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Podcast Ep. 53: How to find and nurture deep friendships with executive matchmaker, Sophy Singer

In this episode

On this episode of the Yes Collective Podcast, we talk to executive matchmaker and mom Sophy Singer. She finds life partners for CEOs, lawyers, and brain surgeons, and on this episode she's bringing her years of experience to the world of friendship. We talk about why it was so much easier to make friends as kids, whether parenthood makes it harder to find really good new friends, how we can find really good new friends in adulthood, how we can nurture these friendships, and so much more. Tune in to hear us dig deep on friendship with the amazing and wise Sophy Singer.

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About our guest

Sophy Singer is an executive matchmaker and founder of Sophy Love, a boutique concierge matchmaking agency. She started her career in matchmaking in 2010 as a dating coach, and found she had both a passion and knack for mentoring people to become their best selves as they played the dating field.

In 2016, she took a leap of faith, quit her job and joined the largest matchmaking firm in the nation. After countless engagements, marriages and babies born as a result of her matches, however, she wanted to get more personal, so in 2018, Sophy branched out and launched her own agency. At Sophy Love, she is able to bring her bubbly, intuitive and unparalleled charm and optimism to every single client. Her service is personal and personalized, and her results speak for themselves.

Transcript highlights

Justin Wilford (JW)

So, Sophie, I do want to start this podcast though, by just surfacing the fact that we are friends that like so we have friends on the podcast, but many of our podcast guests are just experts, therapists, mental health professionals that we bring on. And they share their wisdom with us. But Sophie, we are friends and we are fellow childhood cancer parents. So we have these connections. And so I just want to just like bring that to the surface that this is a conversation among friends. All right. Yes. All right. So let’s do it.

So, Sophie, this month in the Yes collective, the theme is about emotional health and friendships. And so I thought it'd be really awesome because one of the things that we're dealing with throughout the month is how do we make friends, keep friends, maintain friendships as parents. Now we have our lives are full. We are now grown. Well, we're grown ass adults and so how do we do this? And so you came to mind because you are an executive matchmaker. So you help people come together, but of course, for romantic life partnerships. But I thought, oh, maybe Sophie has some wisdom around the friendship thing. So first, you know, I'm just going to ask right after the beginning. Right at the beginning, how do you feel about talking about friendships?

I know your specialty is about romantic matchmaking. Are you okay with this? Like, how do you feel?

Sophy Singer (SS)

100%. Okay. I actually feel like I'm a major expert on friendships, too.

JW

Okay, so. Sophie. Yeah? I have known you. Like, I feel like I've really gotten to know you. Well, maybe, I don't know. Three months or something like you hasn't been at home and already. I do feel like we're really good friends. I'm just like, Oh, Sophie, where else? But I can assure you have like a you have so many friends.

SS

I have a lot of friends. I was thinking about it actually today and I was thinking about it in reflection of listening to the last podcast you guys put up about friendship. And I honestly, I'm very lucky and honestly privileged to have grown up in one place. Basically my whole childhood. We didn't move around, right? We were in San Diego, but like we moved to different parts of San Diego.

But like I was in San Diego from when I was, I don't know, three or four or five. And then we did not move. That was it. And so when I was like six years old, my parents sent me to this Jewish school, San Diego Jewish Academy, and my kids go there now and like I have this group of friends and we just stayed friends.

I mean, it was like all the way through high school. I went to college with some of them. I went to college with Tammy. I mean, most people do not have that. Like I would say, majority of people do not have that. And so we do have this really special group. And again, maybe we've stayed together all these years because we were lucky enough to be together all the years, and we've been together through one another's traumas and all sorts of life events.

But yeah, I do have a lot of friends, but I've always loved making friends everywhere and I'm still really good friends, like best friends with like a handful of my college besties and then work and that, I don't know, I just keep gathering them.

JW

So it's not your profession and expertise, but you do have a natural expertise around friendships.

SS

So I do, I do. But it really the more I thought about this going into this podcast, friendship, platonic friendship as adults and dating really have a lot of parallel.

JW

All right. So let's get into it first. I would love to know, how did you even get into this? This is such a unique field. When I first heard that this is what you do for a living. Like, my mom was like, what? Oh, I thought that was only in the movies. I but yeah, this is a real thing.

SS

Yeah. And my husband always says whenever I say my wife is a professional matchmaker, he's like, Jeff Bezos could be in the room and everybody will just turn and be like, Wait, what? Tell me about it. And people are like, oh, you do that for a living. Like you make money. And I'm like, Yeah, that's my job. So it happened. I was just kind of called to it through my own life experience. I broke off an engagement in my late twenties and I was kind of back on the dating scene, full blown, like looking for a husband and like a baby daddy.

I was like, I need to get married, have kids, because that's like the next thing. And most of my friends were already married and starting to have families by then. And so I was like really behind. And then I had to do online dating and that was kind of a trip. And so I had never dated before really.

I had just had like a handful of like serious boyfriends. So dating was really difficult emotionally. I mean, it's just a roller coaster and it can like really mess you up. And so it was hard. And so I had like a therapist for these years that I was dating and I had a couple of people that I kind of went to as like mentors to just really help me.

I called it like the trenches of dating, like when you're actually actively dating and then you throw in online dating where there's like all these options and you go on a date and then the next day you see you go on the website and you see that the guy you went out with last night, also online right now, why is he online?

JW

It's so weird to me. So Audra and I met in college. I mean, I was I think it was 19 and like, we dated other people for a long time, but and so I don't think we became romantically involved until  maybe 23 or 24, but but it was like, boom, we're getting married. And here we are. This. Yeah. Like there was no if there was online dating in 1999 of the year 2000 or whenever, like I don't, I don't think there was. But it just it is the way things are now, but is it like is it worse? Do you think people actually had it better before the Internet?

SS

What's so hard to say? But I'm going to say, yes, they had it better. The options are so much more plentiful. And honestly, I met my husband online. So why am I saying this? But ha, it is brutal. It's just so brutal.

JW

And you said the trenches and. Yeah, it's it's trenches. Trenches and it's like, oh my God, that's like that is a World War one metaphor, you know.

SS

That's how I felt. I felt like I was emotionally getting beat up and it was really hard. And I was calling my therapist all the time like, what is going on? Like just all these weird things happening, right? Like you go on a date, you kiss a guy good night, then you go home. You're kind of butterflies and, oh, like thinking about what could be.

And then the next day you get like a pop up notification that someone messaged you and you go on the app and you see that they messaged you and you're like, Oh, but then you notice that the guy you just went out with online now like you could see that he's logged in and like what a mind f like you're like, wait, what it was I just remember being like, this is so messed up from the beginning.

So anyway, it was, it was pretty gnarly. But I, it also, you know, there's just anyway, there's so much to it. So I ended up dating a lot online, offline. I met people, I traveled for work, I was meeting people at trade shows and having long distance boyfriends. And in the end, like I was the go to girl.

First of all, everybody loved hearing my dating stories because I share I'm a sharer as you know. So, yeah, so I would be like, Oh my God, check out this crazy date. I went like, it was just comedic, you know? It was like I had all the good stories and then and I'm really open, so I'll share every detail.

And everybody was like, all over that. And then I got really good at dating. Like, it took me years of, like, therapy and practice and I got good at it. And so then people started sending me their friends like, Oh, Sophie, you need dating advice or you need help with your profile or whatever. They would send me people and then I started charging hourly for that on the side of like my regular job.

And I really enjoyed it and I was like, Yeah, this is cool. And then when I met my goal, it was like, Oh, she did it. Like then suddenly I got a lot of referrals and I really enjoyed it and I was like, It would be so amazing to have a career where I can, like, relieve the discomfort of this for other people and make it easier, just easier to navigate until you find your person, right.

And so I did the date coaching and then after I had the twins, I was like, in between jobs, I couldn't travel anymore. And someone posted, my cousin's friend posted that the matchmaker agency she worked at was hiring. And they were pretty small then. I mean, not small, but compared to now, it's like the largest matchmaking agency in the country.

So I got hired and I mean, within three months I had a couple engaged that I had set up and I was like, this is it. Like this is I love this. It was my jam. Yeah, it was cool. So. Yeah. So that you were hooked?

JW

Yeah, you were hooked. Yeah. All right. So transitioning into this friendship thing here, so I'm now curious as you've had a chance to reflect and I mean, this is kind of obvious, but I really like to start in the most obvious places. What is the difference between a romantic life partnership and friendship? Is it is it just sex?

I mean, if you if you take sex out of it, like, is it basically the same thing? What do you think?

SS

Yeah. So, I mean, I think sex, the physical intimacy is like the obvious main difference between the two. But even the way you approach it to like approach a potential life partner or romantic partner versus a friend. So when you go in to when you're meeting a new person, if your intentions are to date immediately, your mindset is like, Am I attracted to them?

Can I see myself spending my life with them? Like I was dating and I was like interviewing fathers and husbands really. And that's what my clients do too. And I'm like, Stop, stop doing that. But we all do it naturally. That's how you go into a dating scenario. Whereas when you meet a new person without any.

JW

So when you said that you interview fathers and husbands, do you mean you're interviewing this person for the role of. Yes and yes, yes. Yes. Right. And so that would be a big difference because when when you are getting to know somebody to see if they're going to be a friend, you don't have them pegged in like, no, you're going to be a friend who does this with me or you're going to be that friend, or you're just like, let's hang.

SS

Right. But it puts so much less pressure on the connection. And I try to encourage my clients all the time, like let go of the outcome. Like, I know I'm setting you up on a date, but like just see if you want to hang out with this person again. Like go in as if you're maybe meeting a friend, a business partner, who knows, right?

There's so much pressure when people go on a date and then there's like they're they're like, oh, my God, is there a spark? Am I attracted to them? You don't think that when you meet a friend at a party, when you get you know, like if you're talking to a new person, you're not like, oh, like, do I want to take your clothes off? Like, I might, you know, like, there's just none of that usually.

JW

So you take out the physical. Yeah, the physical part of it. And then but this other part is really similar. You're thinking, do I want to spend more time with this person?

SS

Like, do we want a second date? Yeah. Like I tell people, the purpose of a first date is to find out if you want to go on a second date. It is not to find out if this will be your future husband, wife, parent of your children. None of that. I mean, and that's so but but when you take physical intimacy, I think what happens is like when two people meet, right.

And they could have just been friends. But then there's the physical connection and there's some sort of a hookup. Right. Happens. All what this does is it adds this new layer of feelings. And the feelings come from a physical, logical process. Right? Like there's this amazing hormone that I love to talk about called oxytocin. And oxytocin can really mess us up.

I mean, especially women. Are you familiar with oxytocin and all the wonderful things that does?

JW

And hugging, bonding hormone? Yeah.

SS

Yup. And women tend to release a lot of oxytocin, much more than men actually are. We produce a lot more and we release it a lot, a lot of it when we're breastfeeding our children and also when we have an orgasm. And so and men do, too, but women and so this creates this like extra layer of feeling and attachment that feels very real.

And then suddenly there's like new rules around and reactions and emotions around this new connection, right? So if you meet someone, you hang out, you have dinner, you have a great night, you say good night. Bye. And they don't text you the next day. You're not probably even thinking about it much. Like maybe you're like, Oh, I would like to hang out with that person again.

But if you hooked up that night, the next morning, if you are women especially, but men also. You are. You've got that phone out. Who's going to text? Who are they going to text me? Am I going to see them again? Oh, so much starts happening, right?

JW

Yeah. So automatically I'm hearing this, there are levels then when we're talking about romantic relationship. So if you just go out on that first date and you just talk, you have a good time. Nothing happens beyond that. And so you're you're out like maybe just the first level. Like, I don't know, friendship. Yeah. You know, we'll, we'll like, we'll see if we, you know, connect again.

And then the next level up is like, okay, well, if we hook up, you know, then, then we're on to now another level I would imagine. I mean, I, this world is so, so far in the past for me, I'm imagining at least one other level before life partnership. We're together forever. But there are these levels to romantic relationships.

And so I'm curious if you see these same levels in friendships. I mean, yes, like we know like. Okay, that's an acquaintance and that's a really good friend. Do you see the same thing?

SS

Yeah, I think. But what's cool, yes, there are obviously different levels of friendship and also but but the best part about friendship is that they're so much more fluid. So it's really hard in romantic relationships to go back a level you can't. It's really hard to backpedal. Like really hard.

JW

Oh, I haven't thought about that. Yeah.

SS

Yes. So, so when you make a new friend or even with friendships that I've had my whole life, oh my God, there's such an ebb and flow to those friendships or even the friendships I've had for the last five years, nine years, two years, five months. It doesn't matter. It's like there's just this ebb and flow and both people can show up as much or as little as they want to or can, and that like like the parameters are. So there's just so much more elasticity to it.

JW

That's fascinating. So yeah, though that that yeah. So you can't go back in these romantic ways. And that's why when, when there's a divorced couple and we hear that they're still friends and that like everything's cool and they can still hang out, like that's mind blowing. Like what? Because. Yeah, and that's because of this assumption. Like, you just can't go back, love.

SS
Well, yeah. And that becomes really complicated too, because, you know, parents, single, you know, divorced couples who have to they have to co-parent. Usually you would hope that they are right and a very close warm amicable co parenting relationship is really like ideal for the kids. Right. And every everybody really. But then you have these people who are dating and meeting new partners and then the new partners are like, wait, they're like so close with their ex.

Like this feels threatening and so I, I just feel like, I think that as adults and as parents, I think it's just important not to put so much pressure on our, our husbands, wives, spouses, life partners to give us all of that, that friendship. Right? Like we can't get it all from one person. The rules are set for our life partnership.

Okay? Like you've hooked up a ton. You're married, you've got kids. There's like, all these. I mean, that's really has very little flexibility, to be honest, you know, and so I think that's why having friendships as an adult, as a parent outside of your home life partnership is so important. It really is.

JW

I just I just remember one of the really great quotes from the podcast that we released at the beginning of August with Blake, and she says that she thinks about friendships as living organisms. and I love that because like you really, you cultivate it, you nurture it. And, and, you know, like things change. There is this like developmental arc. But I would I have to think that romantic partnerships are also living organisms like they are. The other thing that they have all these rules and they're more structured.

And so I was thinking, okay, what's the difference between these living organisms? And I don't know, this just popped into my head. The romantic relationship is the living organism where you're like, this thing has to bear fruit, like, because this is what I, I'm going to need the fruit to survive. Like I'm going to need the fruit too.

Like, yes. So it's like, oh my God, like, I cannot mess this thing up. But then the other friendships can kind of come and go. It's like, you don't need a flower, you don't need to produce any fruit. Maybe sometimes you will and maybe sometimes you won't. But it's like.

SS

I love that. That's really great. Yes, I love that. That's true. I think it's like that our life partnership should be where we put the most kind of focus and energy on nurturing. Right. And the nice thing is that the more connections you have outside of that, the less kind of pressure there is right to like make everything at home feel perfect if you have if you're if you're getting your emotional needs met in multiple different ways.

Right, because one person can't do it all, you know. Right. Yeah. So, yes.

JW

Yeah. That's that's a that's a big thing. I in previous academic life, one of the things I love to study was this transition, like basically this transition from old world traditional communities to these modern societies that we now live in. And that if we, we can we we can actually trace the history of love and like like the history of paired partnerships and that they used to be part of these large social networks, you know.

And so we wouldn't expect all of our needs to be met by just one other person. But then the world comes along. And in these modern societies, like, Oh my God, now all everything I need in life is put on to this other person. So, right, I'm imagining now that this is probably a really big reason why friendship is so important. Like, is this the key for you?

SS

I think it is, honestly. And I, as a matchmaker, I mean, look, obviously, my clients hire me to find them a romantic partner. But oftentimes I watch these connections unfold as friendships and those have happened to me also. So I have a lot of friends that I made over the years that started as a first date.

JW

So do you have any friendships where things get really serious and then you were able to pull it back to friendship because that is what you mentioned before you like. It's really hard to go back.

SS

Okay. Those friendship. Yes, I'm still friends with men I actually dated, which my husband and I laugh about all the time. Like he'll meet someone and be like, Has he seen you naked?

Maybe, maybe not. I don't know. We're cool. Like, he has his own list and I have mine, so we're cool. Like, it's all good. Like, we're like we neither of us are bothered by it, but so yes, I happen to be, but I'll tell you, those friends are not they're not people I'm friends with, like talk to on a very regular basis, but they're still like, we're in each other's lives.

We hop in and out when it feels right. We're connected. I mean, look, Facebook, Instagram, it's just so easy to stay connected, very loose, like on such a surface level.

JW

Okay, so that's a good yeah. I think just because we, we earlier we mentioned how the online situation just being online social media everything has affected the dating scene. How do you think it's affected friendship?

SS

Oh, honestly, I think it's actually amazing for friendship. I, I love it. I encourage parents. So like I said, I'm so lucky that I have friends still that I talk to every day almost for like 39 years. That's very unusual. But I think that a lot of times, like I've had people reach out to me on Facebook or I've reached out to them just because I felt this like, Oh, I saw a post from like an old friend.

I'll just send her a message because that really touched me. Not a public message, like, not a comment, like a direct message. And then suddenly we like this, like we rekindle this little connection, and then sometimes that turns into something really seasonal but amazing. And so I think that a lot of times people are insecure about like, oh, I would love to reconnect with that person.

Like, do it. There you go. It's so easy. You're hiding behind a computer screen and you never know. Like, you might just reach out and, like, have this. This like a new spark happen again, right? With, like, an old friend and get on a face time and then end up planning a trip to see each other. If you don't live in the same place, or sometimes people will move from with another, like let's say you grew up with somebody and then they live somewhere further, like somewhere else.

And then you realize that they moved back. Hi, like go grab coffee or say hi. I think it's so hard for working parents and just all parents to create and, you know, create friendships and also meet new people. You can also go back to connections that you've had from so long ago. And I think Facebook is a really great way to do that or Instagram.

JW

Well, that's really yeah, the connections that we had so long ago and then reconnecting with those people. I've had this experience as well. It's like, Oh, we were like really good high school friends and then we lost track and then, oh, now we're connecting again and it's almost like this instant, like we can just pick back up. Yes, but making a new friendship at like I'm 45 years old, making a new friendship today.

Well, with you, Sophy, has been just a breeze. But beyond that, you know, it's like it's it's more challenging. And so what do you think makes it so different? Like, why is it so much easier to make friends when we're kids and and teenagers than it is to make friends as adults?

SS

Oh, God. Because kids are just so Zen like moment, like, in the moment, like, oh, cool. We're like playing the same, like, video game right now on our phones, like, whatever, right? Like, I watched I watched Audrey the other night. Sit down next to my friend Sydney's son, and suddenly, like they had never met before, they were playing war with cards.

We're like, Here's a deck of cards. They just went at it. Like, I was like, Oh God, this is so awesome. Like, it's so hard to even they're playing because they're playing and as adults we don't play that much anymore. We're just like, our brains are so like going.

JW

Okay, so that, okay, what, what just popped into my head as I'm thinking. Absolutely. I totally remember that being in elementary school and how much easier it would, how easy it was to make friends be like, we're just going to go out on the playground and play soccer together. Or, you know what? It's just, boom, we're all we're all together.

And there's this play. But then, of course, middle school comes along, things get often it's weird and hard and I remember that that that's how I felt. And then on into high school and you know, I connected with some friends. What I'm about to say, though, I want to say parents, if you're listening to this in the car and you don't want your children to hear anything about about ex, if you don't want them to hear things about high school that you would rather than not.

So one thing that I'm realizing is one of the reasons I really got into smoking cannabis. I call him cannabis now to be proper you. Yeah we I had ever in high school is that it was like an instant way to connect with other it totally it was like okay basically what toys and playing were when when I was a kid it was like, oh, you smoke weed I smoke weed.

We can hang. And then boom, the walls come back now and now we're connected and boom. My social network expanded so much because of like oh minded too.

SS

I mean, weed and alcohol were just wonderful for that. Like, yes, all the walls come down like all the like, you know, the anxiety, the social anxiety, the neuroses, like all that.

JW

Well, it does also have have. Yeah. So that stuff comes down. But it was always just like the simple act of just. Oh, yeah, just like, oh yeah, doing something together. And this, this is connected.

SS

Here. Hit this, hit this. Yeah. Hey. Yeah.

JW

Well, that's another thing. Yeah. So now as a as an adult, as a parent, I imagine if I developed a, like, regular cannabis habit, I might be able to expand my friendship again. But outside of that, I don't know. I don't know how.

SS

That's going to like, effect your productivity now.

JW

And I don't know exactly, but it does help me to reflect on maybe why it might be harder to make new friends as an adult. So, Sophie, how. Yeah. Can can can you, can you speak a little bit about this? How so? Well, let's just let's just start. Start here. How do you make new friends otherwise? What is your way?

Like, how do you do it for yourself? So.

SS

Okay, so I was thinking about it before we did this. Like the friends I've made as a parent, like new friends, right? That came after I had children. And it's really hard because our free time shrinks to basically nothing at first. I mean, it’s so precious. You just don't you're like, I don't want to spend any of my free time with anyone unless this is like the shit. Sorry. Like, it's just you can't even. It's like gold. It's like it's just you're so and I'm so picky about it. And and to be honest, this really does parallel with what I do for people for a living.

I mean, these people are like busy executive, single parents running their businesses. They're paying me for that time to like find people, meet them, sort through them, and then just give them like the nuggets like that are really good potentials, but you can't do that with friendship. So I encourage, like I found that like my best friends and really like to today I would say to date I have like probably one really, really close friend that I made after my kids were born.

Like, maybe more. But my friend Kim comes to mine and she was just here yesterday. Her twins and my twins went preschool together.

And so we would sit on the playground and talk and just. Just shoot the shit. Like, we would be like. Okay. And we became. Well, it didn't obviously help that Sasha and Audrey and Lillian, they were just like more like happiest together. But we really like, really liked each other. And she would ask me for dating advice because I'm a matchmaker.

And I was actually there at the day she told me about her first date with her husband that she just married two weeks ago. So that was seven years ago. So it was just and what I what I'm getting at is, if possible, when your children are young and you do supervised playdates, where it's a playground or it's someone's house, you don't just drop off a four year old at someone's house.

You're there with the other parent. That is like a really good time to screen them as a friend. Right? I call it screening and matchmaking. I'm going to screen this match for you, but it's just a little kind of forced together time. But it's limited. It's like a first date. You're like your kids are playing and you can chat and.


JW

It has this, well, I like to use the word like instrumental. So it's like, we're not really doing this because we're screening each other, right? Because we need to supervise our kids. And so super low stakes that it like like I have no obligation to reach back out to you. You have no obligation to reach back. Right. So it's like as low stakes.

SS

Absolutely. Exactly. So there's just no pressure and you could get to know and then and then like if things are jiving, you're like, okay, like this could be a front again. It all goes back to letting go of the outcome. Like, I'm like when you're not focused on the outcome of a human connection, I think it just allows things to just organically unfold however they're going to unfold.

And so and it's nice look, but not all of us have little kids anymore. So look, my my twins are nine now. I mean, the other day, I had a mom approach me at camp who was like, hey, our girls really like each other. Can I give you can I get your number? Like, I want to do a playdate with that? And I was like, whoa, this is moving like really fast. What's my number?

JW

Yeah, like, that's the equivalent of like, like kissing before we've even gotten ach other's names. Yeah.

SS

It was really like, whoa. I was like, this is like we just jumped to second base right away, but yeah. Slow your roll. Exactly. And it does get awkward also, I think like sometimes when our kids make friends and then you're like with the other parents or you're at a birthday party or whatever, and then like other parent, another parent is like, Oh, we should get a, we should do a double date, you know, and I'm in my head thinking.

JW

There is no way this woman do that. Okay. So I've, I've two things. First, I'm like if I think of people on a spectrum, yeah, a whole continuum of like people are just naturally super social and boom, boom, they're out there. And then people who are more introverted and quiet and to themselves. So if I think you are on the far end of the more social spectrum, like you are like I am, you're you're out there, you're connecting, you are an actor.

That's why you're such a good executive matchmaker. But I want to like slow down just a little bit and recognize that for a lot of people who are going to be on the other end, who are going to be more introverted, are going to be much more maybe in their heads about that interaction of, yeah, how do I approach another parent?

How do I know? Like they might be the the parent who, who goes too fast because they're like, I don't know how to like, you know, how do I approach that? Like, I think I might be friends with this person or I could be I could see myself becoming friends with this person. So I'm going to ask and see if they want to go on a play date with our kids.

What advice do you have for that parent who is more introverted and is like looking for ways to connect and is afraid of moving too fast?

SS

Don't move too fast. Just think of like a really like ask them on a first date. So, so first parent, mom, dad date. I don't know. To me that is like, like, first of all, if your kids are young enough to do the play date, that's a perfect go to like, let's do a play date. That's a no brainer.

Again, that goes back to like, we're just doing this for our kids and then you can see how that goes. So but for those of us who have older kids, like I dropped Sasha off on that playdate, I wasn't there. I mean, I was just like, good luck. You seem cool. Yeah.

I was really kind of rolling dice there. But but no, but like for people who have older kids, like, you know, nine, ten, 11, whatever, and they're there, but they're like noticing that there is another parent that through the school or wherever or through activities that the kids do. I mean, you can do a couple of different things.

So first of all, you could do something really low pressure like, Hey, we should grab coffee sometime or Hey, after drop off, do you want to like grab coffee or something? A little lower stakes than we should get a glass of wine or we should go out in the evening evenings to have more pressure in general. And by the way, as a matchmaker, I actually highly discourage coffee dates because they're so horrifically unsexy and unromantic.

And so they feel more like a very platonic or even interview. So I'm just like, those are perfect for like and again, you have to think about whether that parent works. Maybe they drop their kid off and go right to work, whereas others don't or have more flexible. I've had people approach me and be like because they know that I go for walks after drop off some time.

Like if you both if like just find something that, you know, maybe the two of you have in common, right? Like if you're both people who probably work out like, hey, do you want to go for a like drop after we drop off our kids or whatever? Like go for a quick walk or a hike or like I said, just really low pressure. Coffee is just so easy. It's just.

JW

Real. Yeah, I'm going to do all this because I. This is just sticking in. My brain went to be good. Okay. Sorry for the romantic matchmaking sphere for a new so people that you're connecting for the first time if they do go out on that coffee date because it's so unsexy and so and romantic that then if there's a connection in that context, then boom, you've you've hit gold.

It's kind of like a way to really see, like, okay, the, like, take, take away all the other stuff is, is there a connection?

SS

You're challenging me. Because I really hate coffee dates for four dates. I guess you're right. Like, I'm actually being like, I'm contradicting myself because I'm telling you, let go of the outcome. Go in. Like you're meeting a new person, a friend, but also coffee dates are really not sexy and romance. They don't just don't lend themselves like there's just and honestly, I'm not I'm not like hard core. Like there are certain people who I match who I actually think do need to go on more of a coffee smoothie non standard date but remember these people are paying me a lot to achieve the romantic outcome.

JW

And so throwing them into just a Starbucks and a like egg like. Right, that's not Starbucks. Broad daylight.

SS

Caffeine. You're drinking caffeine. And you're just like, it's so nerve wracking to go on a first date. A coffee can really like, really exacerbate nerves. People interview for jobs at a coffeehouse like.

JW

All that, all that. And yeah. So I am affirming you or your choice there, but just that thought came up as like if in all these barriers a connection is made, then you know, yes, the goal like I have yet.

SS

I mean I have yet to see to have matched a couple successfully where their first date was a coffee date. So and I've sent out over 1500.

JW

Yeah, yeah. Right, right. It's A lot. You, you have some experience there. Yes.

SS

Yeah. So I don't know. It's just but but for friendship and for parents, it's awesome. And it's just I love it. Like, I love that idea and it's just like super low pressure. The other thing that kind of comes up for me though, is when another parent approaches me, right? Or maybe you're more introverted parent, right? And a person and some crazy extrovert like me comes over and is like, Oh, we should like, let's go for a hike or whatever.

And you're like, Wait, I don't know. It feels it could be like really uncomfortable in that moment because it's really hard for people, even extroverted people like me, to be honest in the it's really hard to like reject someone, right? Or like, God, it's so hard, so hard. So I thought about this and like I give this type of advice to all my clients who go on dates and at the end there's the so like, we should do this again.

I had a really good time and like, how do you respond if you're not sure, right? Or whatever. So I would say, like, if you're that kind of a little bit more like introverted person and you're being approached by a very outgoing person like me, I think like a really nice way to respond is to give yourself a, like, more time, right?

Like, Oh yeah, that could be fun. Let's text and see what, like what we can arrange over the next few weeks. Few weeks. That's like plenty of time. There's no, like, pressure. Not like this week or tomorrow. And then you can go home and think about it and decide and then like move slow. So I just kind of wanted to put that out there.

Yeah, because it's really hard sometimes for people and even for me sometimes, you know, to be like, No, that doesn't actually sound like something I want to do right now. Like, I'm too busy a new person. I don't know you well enough, you know? So, yeah. So that, that also kind of popped in my head as I was thinking about parent dating and friend friendship dating in the parenting world.

JW

I want to also talk about breaking up. And so I don't know. Now you're not I imagine you don't have really you're not there for the romantic breakup. You're there to put people together.

SS

No, I'm there for you. I'm there for both. Oh, no, no, no, no, no, no. I'm there for some a lot. Oh, yeah. Because I mean, I imagine a lot of people who will date and then they'll date for two or three months and then realize, all right, like, okay.

JW

Okay, there's a lot.

There are sometimes friendships where it's time to break up. I mean, if it happens. So, yeah, how can you help us think about letting go of a friendship when that time has come?

SS

Well, first of all, it's like deciding right for yourself. Like, is this friendship serving me anymore? Like what? What is. What's what's going on here? I found this happened to me in my life multiple times. Where I a couple times where even somebody that I knew from when I was in college, you know, and we had been like best friends.

So actually it happened with my roommate, one of my roommates in college. We lived together for four years in our lives. Just took these like really different paths. And she moved to San Diego at some point and just was like suddenly integrated with my friend group. Or I was obviously like, Oh my God, you're in San Diego. Like, Let's hang out and it didn't work well.

Like it was just like really uncomfortable for her. For me, she felt a lot of like it was just it just wasn't a fit at the time. We were in like really different places in life and eventually it hit like a breakup. And I think we were just like, like at that point, this is like with a history with someone, right?

Like we had to like have an honest conversation about it and it was more just like, listen, like this is not working like ever. Like, I don't feel good when we interact, when we talk. But I don't think that most friendship break ups happen that way. That was like a very honest, raw, long term one. I think sometimes honestly, things just fizzle.

Like, Have you ever had that happen?

JW

Well, that's that ebb and flow. And right where there's just an ebb and it never flows again.

SS

Exactly. And I think I think you need to just think about what a friendship, how that friend makes you feel like. How do you feel when they when you even get a text from them? And I actually just it's funny enough, I just had a conversation I think yesterday or the day before with a girlfriend of mine. I think I even told you about it, Justin, who went on to tell me, Oh, I'm having I'm going to an IFS lecture tonight like we had actually not, we've known each other since we were very little.

She's part of that crew, the Jew crew and we had really like drifted apart. And that was conscious on her part for the last few years. And yesterday or the day before we talked and she told me, I've just pulled back from you because I felt judged. I felt like you were always trying to fix my single hood.

My I mean, it was really and I actually knew it deep down inside. I knew it couldn't help myself with her before and then. Now it just it was pretty rad because we had this, like, amazing conversation. And I almost feel like we just got back together.

So I think you just need to decide. And that's what she did. She decided it for herself. I was reaching out to her all the time and she was like, Aha, aha. Like she was blowing me off as a friend and I didn't push because I kind of knew I'm like, This isn't she's not down for this right now.

And I think we just all need to be aware of like a, how we feel in a friendship and when it's time to sort of back off or let them back off, you back off, whatever it is, right? Yeah. So that's kind of my.

JW

Thought on that mean last friendship question and never will go into our our final three. Mm hmm. Well, I want to just briefly talk about being a parent and being friends with other parents. That makes sense. But being a parent and being friends with non-parents there feels to me like there's a gap there. Like I can think about my non parent friends and we're like we're friends.

But it's like there's something, we're like, you don't really get my life because being a parent is so radically different way. It just changes everything. So I'm curious, first off, do you have any non parent friends who are like super, super good friends? Yeah, I do. Oh I was. I did.

SS

Again, it's going to parallel a parallels to dating also and I'm I'm doing this because I'm so matchmaker Sophie talking here this is such a catch 22 in dating because single parents are like, oh my God, I like, I want to meet somebody who gets it, who gets the, like, all consuming existence of being a parent. It's just all consuming.

And you're like, Oh, I just want somebody. And then but then the problem is, and I think this problem comes in also with adult with with parent friends, right. If you were at the mercy of our children's schedules, activities, illnesses, medical emergency, medical conditions, I mean, yeah.

Just throw those some big medical conditions in the mix. I mean, suddenly you're like, when can and then the other parent has their things. And that happens with dating too. It's like, sure, we get each other and when we're together and connecting there is so that understanding. And so there's this like bond and understanding and connection that happens between two parents, both in dating and friendship, but logistics.

It becomes really logistical sometimes, and it's almost difficult to make time or for them to make time and you guys to have the right times line up, to spend time together, talk to each other, even on the phone right. Okay.

JW

So I just realized that I that I have this because I do have several really good non parent friends like just dear, dear, non-parent friends and just realize I carry this silent suppressed judgment any time that we're trying to connect and their schedule is somehow blocked off. And I'm just like, what are you doing? Like you have kids, you do not I I'm sorry.

Whatever is how I do that. Your life I guess that's juggling like I do that you should be able to fit into my schedule right.

SS

And that's we have to be careful as parents not to do that. I do the same thing. So I have to I would say to really close friends both from college who are like two of my best friends. I know I say that about a lot of people just end, but they are there's like a very. Yes, trust me, if you ask them, they're going to say the same thing.

So but they're both from college and they're both unmarried with no kids. And there's just something so great about connecting them. And suddenly I'm not just talking about my kids the whole time. Suddenly I am Sophie. Pre-mom Sophie and it's awesome. It's amazing to be able to just reconnect with like who we are, the parts of us that aren't a parent, like we're not, you know what I mean? Like who we were before we were parents and just it when I am with my friends, we talk to the ones that are married with kids. Like we talk about our kids and our husbands and our wives and our everything.

Like, it's just like those conversations just keep happening. It does. It's, like, impossible to get away from them. But it's so fun to sit down with somebody who isn't all consumed by that. And then suddenly you're like, Oh my God, there's this whole other part of me that I miss. Yeah. So I think it's important and nice and I really, I really enjoy that. But I do the same thing, by the way. I'm like, What? You're busy. Like, what in God's name could you be doing right now?

JW

It's like, I love, Oh, all right. So at the end of every podcast, we ask our guests these three questions, so we just roll. Rotherham Just and I love how we can compare how each each guest answers these. So the first one is Sophie, if you could put a giant Post-it note on every parent's fridge tomorrow morning, they wake up, boom, the post-it note is there. What does it say?

SS

Okay, this is going to sound like kind of generic, but it's just it's what I came up with. You can do hard things.

JW

Right? You're tired, you're exhausted. Your kids lunches need to be made. Everybody. The lunch closed and out the door. You can do it. And then after running that gantlet, then you have to go to work and you can do it. Yeah. So Sophie, is there a quote recently that has changed the way you think or feel?

SS

Okay, so I thought about that. I mean, this didn't change the way I think or feel, but it definitely ever since I saw this quote, it like fully embodied my experience as a parent and as like a human in general. It's the real quote. Let everything happen to you, beauty and terror. Just keep going. No feeling is final.

JW

And then finally, what is your favorite thing about kids lately?

SS

I've found that my favorite thing is I love explaining to kids these cons that's in life that are so mundane to us as 45 year old grown ass adults like something as simple as like, I don't know, just like medical insurance. Like they look at a bill and they're like, What is this? And I'm like, Oh, this piece of mail. Here's what's on it. Like, here's how this works.

Here's the medical bill, or here's even like a power bill, whatever. Just like that sense of like the ability that if you kind of just really get into the moment with kids like be present, you can kind of relive that, like, sense of wonder, terror and newness that we just you lose as you get older and live more years, you know?

Podcast Ep. 53: How to find and nurture deep friendships with executive matchmaker, Sophy Singer

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Podcast Ep. 53: How to find and nurture deep friendships with executive matchmaker, Sophy Singer

Executive matchmaker, Sophy Singer, brings her decades of matchmaking skills to our theme of the month: finding and nurturing deep friendships in parenthood.

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In this episode

On this episode of the Yes Collective Podcast, we talk to executive matchmaker and mom Sophy Singer. She finds life partners for CEOs, lawyers, and brain surgeons, and on this episode she's bringing her years of experience to the world of friendship. We talk about why it was so much easier to make friends as kids, whether parenthood makes it harder to find really good new friends, how we can find really good new friends in adulthood, how we can nurture these friendships, and so much more. Tune in to hear us dig deep on friendship with the amazing and wise Sophy Singer.

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About our guest

Sophy Singer is an executive matchmaker and founder of Sophy Love, a boutique concierge matchmaking agency. She started her career in matchmaking in 2010 as a dating coach, and found she had both a passion and knack for mentoring people to become their best selves as they played the dating field.

In 2016, she took a leap of faith, quit her job and joined the largest matchmaking firm in the nation. After countless engagements, marriages and babies born as a result of her matches, however, she wanted to get more personal, so in 2018, Sophy branched out and launched her own agency. At Sophy Love, she is able to bring her bubbly, intuitive and unparalleled charm and optimism to every single client. Her service is personal and personalized, and her results speak for themselves.

Transcript highlights

Justin Wilford (JW)

So, Sophie, I do want to start this podcast though, by just surfacing the fact that we are friends that like so we have friends on the podcast, but many of our podcast guests are just experts, therapists, mental health professionals that we bring on. And they share their wisdom with us. But Sophie, we are friends and we are fellow childhood cancer parents. So we have these connections. And so I just want to just like bring that to the surface that this is a conversation among friends. All right. Yes. All right. So let’s do it.

So, Sophie, this month in the Yes collective, the theme is about emotional health and friendships. And so I thought it'd be really awesome because one of the things that we're dealing with throughout the month is how do we make friends, keep friends, maintain friendships as parents. Now we have our lives are full. We are now grown. Well, we're grown ass adults and so how do we do this? And so you came to mind because you are an executive matchmaker. So you help people come together, but of course, for romantic life partnerships. But I thought, oh, maybe Sophie has some wisdom around the friendship thing. So first, you know, I'm just going to ask right after the beginning. Right at the beginning, how do you feel about talking about friendships?

I know your specialty is about romantic matchmaking. Are you okay with this? Like, how do you feel?

Sophy Singer (SS)

100%. Okay. I actually feel like I'm a major expert on friendships, too.

JW

Okay, so. Sophie. Yeah? I have known you. Like, I feel like I've really gotten to know you. Well, maybe, I don't know. Three months or something like you hasn't been at home and already. I do feel like we're really good friends. I'm just like, Oh, Sophie, where else? But I can assure you have like a you have so many friends.

SS

I have a lot of friends. I was thinking about it actually today and I was thinking about it in reflection of listening to the last podcast you guys put up about friendship. And I honestly, I'm very lucky and honestly privileged to have grown up in one place. Basically my whole childhood. We didn't move around, right? We were in San Diego, but like we moved to different parts of San Diego.

But like I was in San Diego from when I was, I don't know, three or four or five. And then we did not move. That was it. And so when I was like six years old, my parents sent me to this Jewish school, San Diego Jewish Academy, and my kids go there now and like I have this group of friends and we just stayed friends.

I mean, it was like all the way through high school. I went to college with some of them. I went to college with Tammy. I mean, most people do not have that. Like I would say, majority of people do not have that. And so we do have this really special group. And again, maybe we've stayed together all these years because we were lucky enough to be together all the years, and we've been together through one another's traumas and all sorts of life events.

But yeah, I do have a lot of friends, but I've always loved making friends everywhere and I'm still really good friends, like best friends with like a handful of my college besties and then work and that, I don't know, I just keep gathering them.

JW

So it's not your profession and expertise, but you do have a natural expertise around friendships.

SS

So I do, I do. But it really the more I thought about this going into this podcast, friendship, platonic friendship as adults and dating really have a lot of parallel.

JW

All right. So let's get into it first. I would love to know, how did you even get into this? This is such a unique field. When I first heard that this is what you do for a living. Like, my mom was like, what? Oh, I thought that was only in the movies. I but yeah, this is a real thing.

SS

Yeah. And my husband always says whenever I say my wife is a professional matchmaker, he's like, Jeff Bezos could be in the room and everybody will just turn and be like, Wait, what? Tell me about it. And people are like, oh, you do that for a living. Like you make money. And I'm like, Yeah, that's my job. So it happened. I was just kind of called to it through my own life experience. I broke off an engagement in my late twenties and I was kind of back on the dating scene, full blown, like looking for a husband and like a baby daddy.

I was like, I need to get married, have kids, because that's like the next thing. And most of my friends were already married and starting to have families by then. And so I was like really behind. And then I had to do online dating and that was kind of a trip. And so I had never dated before really.

I had just had like a handful of like serious boyfriends. So dating was really difficult emotionally. I mean, it's just a roller coaster and it can like really mess you up. And so it was hard. And so I had like a therapist for these years that I was dating and I had a couple of people that I kind of went to as like mentors to just really help me.

I called it like the trenches of dating, like when you're actually actively dating and then you throw in online dating where there's like all these options and you go on a date and then the next day you see you go on the website and you see that the guy you went out with last night, also online right now, why is he online?

JW

It's so weird to me. So Audra and I met in college. I mean, I was I think it was 19 and like, we dated other people for a long time, but and so I don't think we became romantically involved until  maybe 23 or 24, but but it was like, boom, we're getting married. And here we are. This. Yeah. Like there was no if there was online dating in 1999 of the year 2000 or whenever, like I don't, I don't think there was. But it just it is the way things are now, but is it like is it worse? Do you think people actually had it better before the Internet?

SS

What's so hard to say? But I'm going to say, yes, they had it better. The options are so much more plentiful. And honestly, I met my husband online. So why am I saying this? But ha, it is brutal. It's just so brutal.

JW

And you said the trenches and. Yeah, it's it's trenches. Trenches and it's like, oh my God, that's like that is a World War one metaphor, you know.

SS

That's how I felt. I felt like I was emotionally getting beat up and it was really hard. And I was calling my therapist all the time like, what is going on? Like just all these weird things happening, right? Like you go on a date, you kiss a guy good night, then you go home. You're kind of butterflies and, oh, like thinking about what could be.

And then the next day you get like a pop up notification that someone messaged you and you go on the app and you see that they messaged you and you're like, Oh, but then you notice that the guy you just went out with online now like you could see that he's logged in and like what a mind f like you're like, wait, what it was I just remember being like, this is so messed up from the beginning.

So anyway, it was, it was pretty gnarly. But I, it also, you know, there's just anyway, there's so much to it. So I ended up dating a lot online, offline. I met people, I traveled for work, I was meeting people at trade shows and having long distance boyfriends. And in the end, like I was the go to girl.

First of all, everybody loved hearing my dating stories because I share I'm a sharer as you know. So, yeah, so I would be like, Oh my God, check out this crazy date. I went like, it was just comedic, you know? It was like I had all the good stories and then and I'm really open, so I'll share every detail.

And everybody was like, all over that. And then I got really good at dating. Like, it took me years of, like, therapy and practice and I got good at it. And so then people started sending me their friends like, Oh, Sophie, you need dating advice or you need help with your profile or whatever. They would send me people and then I started charging hourly for that on the side of like my regular job.

And I really enjoyed it and I was like, Yeah, this is cool. And then when I met my goal, it was like, Oh, she did it. Like then suddenly I got a lot of referrals and I really enjoyed it and I was like, It would be so amazing to have a career where I can, like, relieve the discomfort of this for other people and make it easier, just easier to navigate until you find your person, right.

And so I did the date coaching and then after I had the twins, I was like, in between jobs, I couldn't travel anymore. And someone posted, my cousin's friend posted that the matchmaker agency she worked at was hiring. And they were pretty small then. I mean, not small, but compared to now, it's like the largest matchmaking agency in the country.

So I got hired and I mean, within three months I had a couple engaged that I had set up and I was like, this is it. Like this is I love this. It was my jam. Yeah, it was cool. So. Yeah. So that you were hooked?

JW

Yeah, you were hooked. Yeah. All right. So transitioning into this friendship thing here, so I'm now curious as you've had a chance to reflect and I mean, this is kind of obvious, but I really like to start in the most obvious places. What is the difference between a romantic life partnership and friendship? Is it is it just sex?

I mean, if you if you take sex out of it, like, is it basically the same thing? What do you think?

SS

Yeah. So, I mean, I think sex, the physical intimacy is like the obvious main difference between the two. But even the way you approach it to like approach a potential life partner or romantic partner versus a friend. So when you go in to when you're meeting a new person, if your intentions are to date immediately, your mindset is like, Am I attracted to them?

Can I see myself spending my life with them? Like I was dating and I was like interviewing fathers and husbands really. And that's what my clients do too. And I'm like, Stop, stop doing that. But we all do it naturally. That's how you go into a dating scenario. Whereas when you meet a new person without any.

JW

So when you said that you interview fathers and husbands, do you mean you're interviewing this person for the role of. Yes and yes, yes. Yes. Right. And so that would be a big difference because when when you are getting to know somebody to see if they're going to be a friend, you don't have them pegged in like, no, you're going to be a friend who does this with me or you're going to be that friend, or you're just like, let's hang.

SS

Right. But it puts so much less pressure on the connection. And I try to encourage my clients all the time, like let go of the outcome. Like, I know I'm setting you up on a date, but like just see if you want to hang out with this person again. Like go in as if you're maybe meeting a friend, a business partner, who knows, right?

There's so much pressure when people go on a date and then there's like they're they're like, oh, my God, is there a spark? Am I attracted to them? You don't think that when you meet a friend at a party, when you get you know, like if you're talking to a new person, you're not like, oh, like, do I want to take your clothes off? Like, I might, you know, like, there's just none of that usually.

JW

So you take out the physical. Yeah, the physical part of it. And then but this other part is really similar. You're thinking, do I want to spend more time with this person?

SS

Like, do we want a second date? Yeah. Like I tell people, the purpose of a first date is to find out if you want to go on a second date. It is not to find out if this will be your future husband, wife, parent of your children. None of that. I mean, and that's so but but when you take physical intimacy, I think what happens is like when two people meet, right.

And they could have just been friends. But then there's the physical connection and there's some sort of a hookup. Right. Happens. All what this does is it adds this new layer of feelings. And the feelings come from a physical, logical process. Right? Like there's this amazing hormone that I love to talk about called oxytocin. And oxytocin can really mess us up.

I mean, especially women. Are you familiar with oxytocin and all the wonderful things that does?

JW

And hugging, bonding hormone? Yeah.

SS

Yup. And women tend to release a lot of oxytocin, much more than men actually are. We produce a lot more and we release it a lot, a lot of it when we're breastfeeding our children and also when we have an orgasm. And so and men do, too, but women and so this creates this like extra layer of feeling and attachment that feels very real.

And then suddenly there's like new rules around and reactions and emotions around this new connection, right? So if you meet someone, you hang out, you have dinner, you have a great night, you say good night. Bye. And they don't text you the next day. You're not probably even thinking about it much. Like maybe you're like, Oh, I would like to hang out with that person again.

But if you hooked up that night, the next morning, if you are women especially, but men also. You are. You've got that phone out. Who's going to text? Who are they going to text me? Am I going to see them again? Oh, so much starts happening, right?

JW

Yeah. So automatically I'm hearing this, there are levels then when we're talking about romantic relationship. So if you just go out on that first date and you just talk, you have a good time. Nothing happens beyond that. And so you're you're out like maybe just the first level. Like, I don't know, friendship. Yeah. You know, we'll, we'll like, we'll see if we, you know, connect again.

And then the next level up is like, okay, well, if we hook up, you know, then, then we're on to now another level I would imagine. I mean, I, this world is so, so far in the past for me, I'm imagining at least one other level before life partnership. We're together forever. But there are these levels to romantic relationships.

And so I'm curious if you see these same levels in friendships. I mean, yes, like we know like. Okay, that's an acquaintance and that's a really good friend. Do you see the same thing?

SS

Yeah, I think. But what's cool, yes, there are obviously different levels of friendship and also but but the best part about friendship is that they're so much more fluid. So it's really hard in romantic relationships to go back a level you can't. It's really hard to backpedal. Like really hard.

JW

Oh, I haven't thought about that. Yeah.

SS

Yes. So, so when you make a new friend or even with friendships that I've had my whole life, oh my God, there's such an ebb and flow to those friendships or even the friendships I've had for the last five years, nine years, two years, five months. It doesn't matter. It's like there's just this ebb and flow and both people can show up as much or as little as they want to or can, and that like like the parameters are. So there's just so much more elasticity to it.

JW

That's fascinating. So yeah, though that that yeah. So you can't go back in these romantic ways. And that's why when, when there's a divorced couple and we hear that they're still friends and that like everything's cool and they can still hang out, like that's mind blowing. Like what? Because. Yeah, and that's because of this assumption. Like, you just can't go back, love.

SS
Well, yeah. And that becomes really complicated too, because, you know, parents, single, you know, divorced couples who have to they have to co-parent. Usually you would hope that they are right and a very close warm amicable co parenting relationship is really like ideal for the kids. Right. And every everybody really. But then you have these people who are dating and meeting new partners and then the new partners are like, wait, they're like so close with their ex.

Like this feels threatening and so I, I just feel like, I think that as adults and as parents, I think it's just important not to put so much pressure on our, our husbands, wives, spouses, life partners to give us all of that, that friendship. Right? Like we can't get it all from one person. The rules are set for our life partnership.

Okay? Like you've hooked up a ton. You're married, you've got kids. There's like, all these. I mean, that's really has very little flexibility, to be honest, you know, and so I think that's why having friendships as an adult, as a parent outside of your home life partnership is so important. It really is.

JW

I just I just remember one of the really great quotes from the podcast that we released at the beginning of August with Blake, and she says that she thinks about friendships as living organisms. and I love that because like you really, you cultivate it, you nurture it. And, and, you know, like things change. There is this like developmental arc. But I would I have to think that romantic partnerships are also living organisms like they are. The other thing that they have all these rules and they're more structured.

And so I was thinking, okay, what's the difference between these living organisms? And I don't know, this just popped into my head. The romantic relationship is the living organism where you're like, this thing has to bear fruit, like, because this is what I, I'm going to need the fruit to survive. Like I'm going to need the fruit too.

Like, yes. So it's like, oh my God, like, I cannot mess this thing up. But then the other friendships can kind of come and go. It's like, you don't need a flower, you don't need to produce any fruit. Maybe sometimes you will and maybe sometimes you won't. But it's like.

SS

I love that. That's really great. Yes, I love that. That's true. I think it's like that our life partnership should be where we put the most kind of focus and energy on nurturing. Right. And the nice thing is that the more connections you have outside of that, the less kind of pressure there is right to like make everything at home feel perfect if you have if you're if you're getting your emotional needs met in multiple different ways.

Right, because one person can't do it all, you know. Right. Yeah. So, yes.

JW

Yeah. That's that's a that's a big thing. I in previous academic life, one of the things I love to study was this transition, like basically this transition from old world traditional communities to these modern societies that we now live in. And that if we, we can we we can actually trace the history of love and like like the history of paired partnerships and that they used to be part of these large social networks, you know.

And so we wouldn't expect all of our needs to be met by just one other person. But then the world comes along. And in these modern societies, like, Oh my God, now all everything I need in life is put on to this other person. So, right, I'm imagining now that this is probably a really big reason why friendship is so important. Like, is this the key for you?

SS

I think it is, honestly. And I, as a matchmaker, I mean, look, obviously, my clients hire me to find them a romantic partner. But oftentimes I watch these connections unfold as friendships and those have happened to me also. So I have a lot of friends that I made over the years that started as a first date.

JW

So do you have any friendships where things get really serious and then you were able to pull it back to friendship because that is what you mentioned before you like. It's really hard to go back.

SS

Okay. Those friendship. Yes, I'm still friends with men I actually dated, which my husband and I laugh about all the time. Like he'll meet someone and be like, Has he seen you naked?

Maybe, maybe not. I don't know. We're cool. Like, he has his own list and I have mine, so we're cool. Like, it's all good. Like, we're like we neither of us are bothered by it, but so yes, I happen to be, but I'll tell you, those friends are not they're not people I'm friends with, like talk to on a very regular basis, but they're still like, we're in each other's lives.

We hop in and out when it feels right. We're connected. I mean, look, Facebook, Instagram, it's just so easy to stay connected, very loose, like on such a surface level.

JW

Okay, so that's a good yeah. I think just because we, we earlier we mentioned how the online situation just being online social media everything has affected the dating scene. How do you think it's affected friendship?

SS

Oh, honestly, I think it's actually amazing for friendship. I, I love it. I encourage parents. So like I said, I'm so lucky that I have friends still that I talk to every day almost for like 39 years. That's very unusual. But I think that a lot of times, like I've had people reach out to me on Facebook or I've reached out to them just because I felt this like, Oh, I saw a post from like an old friend.

I'll just send her a message because that really touched me. Not a public message, like, not a comment, like a direct message. And then suddenly we like this, like we rekindle this little connection, and then sometimes that turns into something really seasonal but amazing. And so I think that a lot of times people are insecure about like, oh, I would love to reconnect with that person.

Like, do it. There you go. It's so easy. You're hiding behind a computer screen and you never know. Like, you might just reach out and, like, have this. This like a new spark happen again, right? With, like, an old friend and get on a face time and then end up planning a trip to see each other. If you don't live in the same place, or sometimes people will move from with another, like let's say you grew up with somebody and then they live somewhere further, like somewhere else.

And then you realize that they moved back. Hi, like go grab coffee or say hi. I think it's so hard for working parents and just all parents to create and, you know, create friendships and also meet new people. You can also go back to connections that you've had from so long ago. And I think Facebook is a really great way to do that or Instagram.

JW

Well, that's really yeah, the connections that we had so long ago and then reconnecting with those people. I've had this experience as well. It's like, Oh, we were like really good high school friends and then we lost track and then, oh, now we're connecting again and it's almost like this instant, like we can just pick back up. Yes, but making a new friendship at like I'm 45 years old, making a new friendship today.

Well, with you, Sophy, has been just a breeze. But beyond that, you know, it's like it's it's more challenging. And so what do you think makes it so different? Like, why is it so much easier to make friends when we're kids and and teenagers than it is to make friends as adults?

SS

Oh, God. Because kids are just so Zen like moment, like, in the moment, like, oh, cool. We're like playing the same, like, video game right now on our phones, like, whatever, right? Like, I watched I watched Audrey the other night. Sit down next to my friend Sydney's son, and suddenly, like they had never met before, they were playing war with cards.

We're like, Here's a deck of cards. They just went at it. Like, I was like, Oh God, this is so awesome. Like, it's so hard to even they're playing because they're playing and as adults we don't play that much anymore. We're just like, our brains are so like going.

JW

Okay, so that, okay, what, what just popped into my head as I'm thinking. Absolutely. I totally remember that being in elementary school and how much easier it would, how easy it was to make friends be like, we're just going to go out on the playground and play soccer together. Or, you know what? It's just, boom, we're all we're all together.

And there's this play. But then, of course, middle school comes along, things get often it's weird and hard and I remember that that that's how I felt. And then on into high school and you know, I connected with some friends. What I'm about to say, though, I want to say parents, if you're listening to this in the car and you don't want your children to hear anything about about ex, if you don't want them to hear things about high school that you would rather than not.

So one thing that I'm realizing is one of the reasons I really got into smoking cannabis. I call him cannabis now to be proper you. Yeah we I had ever in high school is that it was like an instant way to connect with other it totally it was like okay basically what toys and playing were when when I was a kid it was like, oh, you smoke weed I smoke weed.

We can hang. And then boom, the walls come back now and now we're connected and boom. My social network expanded so much because of like oh minded too.

SS

I mean, weed and alcohol were just wonderful for that. Like, yes, all the walls come down like all the like, you know, the anxiety, the social anxiety, the neuroses, like all that.

JW

Well, it does also have have. Yeah. So that stuff comes down. But it was always just like the simple act of just. Oh, yeah, just like, oh yeah, doing something together. And this, this is connected.

SS

Here. Hit this, hit this. Yeah. Hey. Yeah.

JW

Well, that's another thing. Yeah. So now as a as an adult, as a parent, I imagine if I developed a, like, regular cannabis habit, I might be able to expand my friendship again. But outside of that, I don't know. I don't know how.

SS

That's going to like, effect your productivity now.

JW

And I don't know exactly, but it does help me to reflect on maybe why it might be harder to make new friends as an adult. So, Sophie, how. Yeah. Can can can you, can you speak a little bit about this? How so? Well, let's just let's just start. Start here. How do you make new friends otherwise? What is your way?

Like, how do you do it for yourself? So.

SS

Okay, so I was thinking about it before we did this. Like the friends I've made as a parent, like new friends, right? That came after I had children. And it's really hard because our free time shrinks to basically nothing at first. I mean, it’s so precious. You just don't you're like, I don't want to spend any of my free time with anyone unless this is like the shit. Sorry. Like, it's just you can't even. It's like gold. It's like it's just you're so and I'm so picky about it. And and to be honest, this really does parallel with what I do for people for a living.

I mean, these people are like busy executive, single parents running their businesses. They're paying me for that time to like find people, meet them, sort through them, and then just give them like the nuggets like that are really good potentials, but you can't do that with friendship. So I encourage, like I found that like my best friends and really like to today I would say to date I have like probably one really, really close friend that I made after my kids were born.

Like, maybe more. But my friend Kim comes to mine and she was just here yesterday. Her twins and my twins went preschool together.

And so we would sit on the playground and talk and just. Just shoot the shit. Like, we would be like. Okay. And we became. Well, it didn't obviously help that Sasha and Audrey and Lillian, they were just like more like happiest together. But we really like, really liked each other. And she would ask me for dating advice because I'm a matchmaker.

And I was actually there at the day she told me about her first date with her husband that she just married two weeks ago. So that was seven years ago. So it was just and what I what I'm getting at is, if possible, when your children are young and you do supervised playdates, where it's a playground or it's someone's house, you don't just drop off a four year old at someone's house.

You're there with the other parent. That is like a really good time to screen them as a friend. Right? I call it screening and matchmaking. I'm going to screen this match for you, but it's just a little kind of forced together time. But it's limited. It's like a first date. You're like your kids are playing and you can chat and.


JW

It has this, well, I like to use the word like instrumental. So it's like, we're not really doing this because we're screening each other, right? Because we need to supervise our kids. And so super low stakes that it like like I have no obligation to reach back out to you. You have no obligation to reach back. Right. So it's like as low stakes.

SS

Absolutely. Exactly. So there's just no pressure and you could get to know and then and then like if things are jiving, you're like, okay, like this could be a front again. It all goes back to letting go of the outcome. Like, I'm like when you're not focused on the outcome of a human connection, I think it just allows things to just organically unfold however they're going to unfold.

And so and it's nice look, but not all of us have little kids anymore. So look, my my twins are nine now. I mean, the other day, I had a mom approach me at camp who was like, hey, our girls really like each other. Can I give you can I get your number? Like, I want to do a playdate with that? And I was like, whoa, this is moving like really fast. What's my number?

JW

Yeah, like, that's the equivalent of like, like kissing before we've even gotten ach other's names. Yeah.

SS

It was really like, whoa. I was like, this is like we just jumped to second base right away, but yeah. Slow your roll. Exactly. And it does get awkward also, I think like sometimes when our kids make friends and then you're like with the other parents or you're at a birthday party or whatever, and then like other parent, another parent is like, Oh, we should get a, we should do a double date, you know, and I'm in my head thinking.

JW

There is no way this woman do that. Okay. So I've, I've two things. First, I'm like if I think of people on a spectrum, yeah, a whole continuum of like people are just naturally super social and boom, boom, they're out there. And then people who are more introverted and quiet and to themselves. So if I think you are on the far end of the more social spectrum, like you are like I am, you're you're out there, you're connecting, you are an actor.

That's why you're such a good executive matchmaker. But I want to like slow down just a little bit and recognize that for a lot of people who are going to be on the other end, who are going to be more introverted, are going to be much more maybe in their heads about that interaction of, yeah, how do I approach another parent?

How do I know? Like they might be the the parent who, who goes too fast because they're like, I don't know how to like, you know, how do I approach that? Like, I think I might be friends with this person or I could be I could see myself becoming friends with this person. So I'm going to ask and see if they want to go on a play date with our kids.

What advice do you have for that parent who is more introverted and is like looking for ways to connect and is afraid of moving too fast?

SS

Don't move too fast. Just think of like a really like ask them on a first date. So, so first parent, mom, dad date. I don't know. To me that is like, like, first of all, if your kids are young enough to do the play date, that's a perfect go to like, let's do a play date. That's a no brainer.

Again, that goes back to like, we're just doing this for our kids and then you can see how that goes. So but for those of us who have older kids, like I dropped Sasha off on that playdate, I wasn't there. I mean, I was just like, good luck. You seem cool. Yeah.

I was really kind of rolling dice there. But but no, but like for people who have older kids, like, you know, nine, ten, 11, whatever, and they're there, but they're like noticing that there is another parent that through the school or wherever or through activities that the kids do. I mean, you can do a couple of different things.

So first of all, you could do something really low pressure like, Hey, we should grab coffee sometime or Hey, after drop off, do you want to like grab coffee or something? A little lower stakes than we should get a glass of wine or we should go out in the evening evenings to have more pressure in general. And by the way, as a matchmaker, I actually highly discourage coffee dates because they're so horrifically unsexy and unromantic.

And so they feel more like a very platonic or even interview. So I'm just like, those are perfect for like and again, you have to think about whether that parent works. Maybe they drop their kid off and go right to work, whereas others don't or have more flexible. I've had people approach me and be like because they know that I go for walks after drop off some time.

Like if you both if like just find something that, you know, maybe the two of you have in common, right? Like if you're both people who probably work out like, hey, do you want to go for a like drop after we drop off our kids or whatever? Like go for a quick walk or a hike or like I said, just really low pressure. Coffee is just so easy. It's just.

JW

Real. Yeah, I'm going to do all this because I. This is just sticking in. My brain went to be good. Okay. Sorry for the romantic matchmaking sphere for a new so people that you're connecting for the first time if they do go out on that coffee date because it's so unsexy and so and romantic that then if there's a connection in that context, then boom, you've you've hit gold.

It's kind of like a way to really see, like, okay, the, like, take, take away all the other stuff is, is there a connection?

SS

You're challenging me. Because I really hate coffee dates for four dates. I guess you're right. Like, I'm actually being like, I'm contradicting myself because I'm telling you, let go of the outcome. Go in. Like you're meeting a new person, a friend, but also coffee dates are really not sexy and romance. They don't just don't lend themselves like there's just and honestly, I'm not I'm not like hard core. Like there are certain people who I match who I actually think do need to go on more of a coffee smoothie non standard date but remember these people are paying me a lot to achieve the romantic outcome.

JW

And so throwing them into just a Starbucks and a like egg like. Right, that's not Starbucks. Broad daylight.

SS

Caffeine. You're drinking caffeine. And you're just like, it's so nerve wracking to go on a first date. A coffee can really like, really exacerbate nerves. People interview for jobs at a coffeehouse like.

JW

All that, all that. And yeah. So I am affirming you or your choice there, but just that thought came up as like if in all these barriers a connection is made, then you know, yes, the goal like I have yet.

SS

I mean I have yet to see to have matched a couple successfully where their first date was a coffee date. So and I've sent out over 1500.

JW

Yeah, yeah. Right, right. It's A lot. You, you have some experience there. Yes.

SS

Yeah. So I don't know. It's just but but for friendship and for parents, it's awesome. And it's just I love it. Like, I love that idea and it's just like super low pressure. The other thing that kind of comes up for me though, is when another parent approaches me, right? Or maybe you're more introverted parent, right? And a person and some crazy extrovert like me comes over and is like, Oh, we should like, let's go for a hike or whatever.

And you're like, Wait, I don't know. It feels it could be like really uncomfortable in that moment because it's really hard for people, even extroverted people like me, to be honest in the it's really hard to like reject someone, right? Or like, God, it's so hard, so hard. So I thought about this and like I give this type of advice to all my clients who go on dates and at the end there's the so like, we should do this again.

I had a really good time and like, how do you respond if you're not sure, right? Or whatever. So I would say, like, if you're that kind of a little bit more like introverted person and you're being approached by a very outgoing person like me, I think like a really nice way to respond is to give yourself a, like, more time, right?

Like, Oh yeah, that could be fun. Let's text and see what, like what we can arrange over the next few weeks. Few weeks. That's like plenty of time. There's no, like, pressure. Not like this week or tomorrow. And then you can go home and think about it and decide and then like move slow. So I just kind of wanted to put that out there.

Yeah, because it's really hard sometimes for people and even for me sometimes, you know, to be like, No, that doesn't actually sound like something I want to do right now. Like, I'm too busy a new person. I don't know you well enough, you know? So, yeah. So that, that also kind of popped in my head as I was thinking about parent dating and friend friendship dating in the parenting world.

JW

I want to also talk about breaking up. And so I don't know. Now you're not I imagine you don't have really you're not there for the romantic breakup. You're there to put people together.

SS

No, I'm there for you. I'm there for both. Oh, no, no, no, no, no, no. I'm there for some a lot. Oh, yeah. Because I mean, I imagine a lot of people who will date and then they'll date for two or three months and then realize, all right, like, okay.

JW

Okay, there's a lot.

There are sometimes friendships where it's time to break up. I mean, if it happens. So, yeah, how can you help us think about letting go of a friendship when that time has come?

SS

Well, first of all, it's like deciding right for yourself. Like, is this friendship serving me anymore? Like what? What is. What's what's going on here? I found this happened to me in my life multiple times. Where I a couple times where even somebody that I knew from when I was in college, you know, and we had been like best friends.

So actually it happened with my roommate, one of my roommates in college. We lived together for four years in our lives. Just took these like really different paths. And she moved to San Diego at some point and just was like suddenly integrated with my friend group. Or I was obviously like, Oh my God, you're in San Diego. Like, Let's hang out and it didn't work well.

Like it was just like really uncomfortable for her. For me, she felt a lot of like it was just it just wasn't a fit at the time. We were in like really different places in life and eventually it hit like a breakup. And I think we were just like, like at that point, this is like with a history with someone, right?

Like we had to like have an honest conversation about it and it was more just like, listen, like this is not working like ever. Like, I don't feel good when we interact, when we talk. But I don't think that most friendship break ups happen that way. That was like a very honest, raw, long term one. I think sometimes honestly, things just fizzle.

Like, Have you ever had that happen?

JW

Well, that's that ebb and flow. And right where there's just an ebb and it never flows again.

SS

Exactly. And I think I think you need to just think about what a friendship, how that friend makes you feel like. How do you feel when they when you even get a text from them? And I actually just it's funny enough, I just had a conversation I think yesterday or the day before with a girlfriend of mine. I think I even told you about it, Justin, who went on to tell me, Oh, I'm having I'm going to an IFS lecture tonight like we had actually not, we've known each other since we were very little.

She's part of that crew, the Jew crew and we had really like drifted apart. And that was conscious on her part for the last few years. And yesterday or the day before we talked and she told me, I've just pulled back from you because I felt judged. I felt like you were always trying to fix my single hood.

My I mean, it was really and I actually knew it deep down inside. I knew it couldn't help myself with her before and then. Now it just it was pretty rad because we had this, like, amazing conversation. And I almost feel like we just got back together.

So I think you just need to decide. And that's what she did. She decided it for herself. I was reaching out to her all the time and she was like, Aha, aha. Like she was blowing me off as a friend and I didn't push because I kind of knew I'm like, This isn't she's not down for this right now.

And I think we just all need to be aware of like a, how we feel in a friendship and when it's time to sort of back off or let them back off, you back off, whatever it is, right? Yeah. So that's kind of my.

JW

Thought on that mean last friendship question and never will go into our our final three. Mm hmm. Well, I want to just briefly talk about being a parent and being friends with other parents. That makes sense. But being a parent and being friends with non-parents there feels to me like there's a gap there. Like I can think about my non parent friends and we're like we're friends.

But it's like there's something, we're like, you don't really get my life because being a parent is so radically different way. It just changes everything. So I'm curious, first off, do you have any non parent friends who are like super, super good friends? Yeah, I do. Oh I was. I did.

SS

Again, it's going to parallel a parallels to dating also and I'm I'm doing this because I'm so matchmaker Sophie talking here this is such a catch 22 in dating because single parents are like, oh my God, I like, I want to meet somebody who gets it, who gets the, like, all consuming existence of being a parent. It's just all consuming.

And you're like, Oh, I just want somebody. And then but then the problem is, and I think this problem comes in also with adult with with parent friends, right. If you were at the mercy of our children's schedules, activities, illnesses, medical emergency, medical conditions, I mean, yeah.

Just throw those some big medical conditions in the mix. I mean, suddenly you're like, when can and then the other parent has their things. And that happens with dating too. It's like, sure, we get each other and when we're together and connecting there is so that understanding. And so there's this like bond and understanding and connection that happens between two parents, both in dating and friendship, but logistics.

It becomes really logistical sometimes, and it's almost difficult to make time or for them to make time and you guys to have the right times line up, to spend time together, talk to each other, even on the phone right. Okay.

JW

So I just realized that I that I have this because I do have several really good non parent friends like just dear, dear, non-parent friends and just realize I carry this silent suppressed judgment any time that we're trying to connect and their schedule is somehow blocked off. And I'm just like, what are you doing? Like you have kids, you do not I I'm sorry.

Whatever is how I do that. Your life I guess that's juggling like I do that you should be able to fit into my schedule right.

SS

And that's we have to be careful as parents not to do that. I do the same thing. So I have to I would say to really close friends both from college who are like two of my best friends. I know I say that about a lot of people just end, but they are there's like a very. Yes, trust me, if you ask them, they're going to say the same thing.

So but they're both from college and they're both unmarried with no kids. And there's just something so great about connecting them. And suddenly I'm not just talking about my kids the whole time. Suddenly I am Sophie. Pre-mom Sophie and it's awesome. It's amazing to be able to just reconnect with like who we are, the parts of us that aren't a parent, like we're not, you know what I mean? Like who we were before we were parents and just it when I am with my friends, we talk to the ones that are married with kids. Like we talk about our kids and our husbands and our wives and our everything.

Like, it's just like those conversations just keep happening. It does. It's, like, impossible to get away from them. But it's so fun to sit down with somebody who isn't all consumed by that. And then suddenly you're like, Oh my God, there's this whole other part of me that I miss. Yeah. So I think it's important and nice and I really, I really enjoy that. But I do the same thing, by the way. I'm like, What? You're busy. Like, what in God's name could you be doing right now?

JW

It's like, I love, Oh, all right. So at the end of every podcast, we ask our guests these three questions, so we just roll. Rotherham Just and I love how we can compare how each each guest answers these. So the first one is Sophie, if you could put a giant Post-it note on every parent's fridge tomorrow morning, they wake up, boom, the post-it note is there. What does it say?

SS

Okay, this is going to sound like kind of generic, but it's just it's what I came up with. You can do hard things.

JW

Right? You're tired, you're exhausted. Your kids lunches need to be made. Everybody. The lunch closed and out the door. You can do it. And then after running that gantlet, then you have to go to work and you can do it. Yeah. So Sophie, is there a quote recently that has changed the way you think or feel?

SS

Okay, so I thought about that. I mean, this didn't change the way I think or feel, but it definitely ever since I saw this quote, it like fully embodied my experience as a parent and as like a human in general. It's the real quote. Let everything happen to you, beauty and terror. Just keep going. No feeling is final.

JW

And then finally, what is your favorite thing about kids lately?

SS

I've found that my favorite thing is I love explaining to kids these cons that's in life that are so mundane to us as 45 year old grown ass adults like something as simple as like, I don't know, just like medical insurance. Like they look at a bill and they're like, What is this? And I'm like, Oh, this piece of mail. Here's what's on it. Like, here's how this works.

Here's the medical bill, or here's even like a power bill, whatever. Just like that sense of like the ability that if you kind of just really get into the moment with kids like be present, you can kind of relive that, like, sense of wonder, terror and newness that we just you lose as you get older and live more years, you know?

In this episode

On this episode of the Yes Collective Podcast, we talk to executive matchmaker and mom Sophy Singer. She finds life partners for CEOs, lawyers, and brain surgeons, and on this episode she's bringing her years of experience to the world of friendship. We talk about why it was so much easier to make friends as kids, whether parenthood makes it harder to find really good new friends, how we can find really good new friends in adulthood, how we can nurture these friendships, and so much more. Tune in to hear us dig deep on friendship with the amazing and wise Sophy Singer.

Listen here

Listen on Apple Podcasts, Spotify, Stitcher, or Overcast

About our guest

Sophy Singer is an executive matchmaker and founder of Sophy Love, a boutique concierge matchmaking agency. She started her career in matchmaking in 2010 as a dating coach, and found she had both a passion and knack for mentoring people to become their best selves as they played the dating field.

In 2016, she took a leap of faith, quit her job and joined the largest matchmaking firm in the nation. After countless engagements, marriages and babies born as a result of her matches, however, she wanted to get more personal, so in 2018, Sophy branched out and launched her own agency. At Sophy Love, she is able to bring her bubbly, intuitive and unparalleled charm and optimism to every single client. Her service is personal and personalized, and her results speak for themselves.

Transcript highlights

Justin Wilford (JW)

So, Sophie, I do want to start this podcast though, by just surfacing the fact that we are friends that like so we have friends on the podcast, but many of our podcast guests are just experts, therapists, mental health professionals that we bring on. And they share their wisdom with us. But Sophie, we are friends and we are fellow childhood cancer parents. So we have these connections. And so I just want to just like bring that to the surface that this is a conversation among friends. All right. Yes. All right. So let’s do it.

So, Sophie, this month in the Yes collective, the theme is about emotional health and friendships. And so I thought it'd be really awesome because one of the things that we're dealing with throughout the month is how do we make friends, keep friends, maintain friendships as parents. Now we have our lives are full. We are now grown. Well, we're grown ass adults and so how do we do this? And so you came to mind because you are an executive matchmaker. So you help people come together, but of course, for romantic life partnerships. But I thought, oh, maybe Sophie has some wisdom around the friendship thing. So first, you know, I'm just going to ask right after the beginning. Right at the beginning, how do you feel about talking about friendships?

I know your specialty is about romantic matchmaking. Are you okay with this? Like, how do you feel?

Sophy Singer (SS)

100%. Okay. I actually feel like I'm a major expert on friendships, too.

JW

Okay, so. Sophie. Yeah? I have known you. Like, I feel like I've really gotten to know you. Well, maybe, I don't know. Three months or something like you hasn't been at home and already. I do feel like we're really good friends. I'm just like, Oh, Sophie, where else? But I can assure you have like a you have so many friends.

SS

I have a lot of friends. I was thinking about it actually today and I was thinking about it in reflection of listening to the last podcast you guys put up about friendship. And I honestly, I'm very lucky and honestly privileged to have grown up in one place. Basically my whole childhood. We didn't move around, right? We were in San Diego, but like we moved to different parts of San Diego.

But like I was in San Diego from when I was, I don't know, three or four or five. And then we did not move. That was it. And so when I was like six years old, my parents sent me to this Jewish school, San Diego Jewish Academy, and my kids go there now and like I have this group of friends and we just stayed friends.

I mean, it was like all the way through high school. I went to college with some of them. I went to college with Tammy. I mean, most people do not have that. Like I would say, majority of people do not have that. And so we do have this really special group. And again, maybe we've stayed together all these years because we were lucky enough to be together all the years, and we've been together through one another's traumas and all sorts of life events.

But yeah, I do have a lot of friends, but I've always loved making friends everywhere and I'm still really good friends, like best friends with like a handful of my college besties and then work and that, I don't know, I just keep gathering them.

JW

So it's not your profession and expertise, but you do have a natural expertise around friendships.

SS

So I do, I do. But it really the more I thought about this going into this podcast, friendship, platonic friendship as adults and dating really have a lot of parallel.

JW

All right. So let's get into it first. I would love to know, how did you even get into this? This is such a unique field. When I first heard that this is what you do for a living. Like, my mom was like, what? Oh, I thought that was only in the movies. I but yeah, this is a real thing.

SS

Yeah. And my husband always says whenever I say my wife is a professional matchmaker, he's like, Jeff Bezos could be in the room and everybody will just turn and be like, Wait, what? Tell me about it. And people are like, oh, you do that for a living. Like you make money. And I'm like, Yeah, that's my job. So it happened. I was just kind of called to it through my own life experience. I broke off an engagement in my late twenties and I was kind of back on the dating scene, full blown, like looking for a husband and like a baby daddy.

I was like, I need to get married, have kids, because that's like the next thing. And most of my friends were already married and starting to have families by then. And so I was like really behind. And then I had to do online dating and that was kind of a trip. And so I had never dated before really.

I had just had like a handful of like serious boyfriends. So dating was really difficult emotionally. I mean, it's just a roller coaster and it can like really mess you up. And so it was hard. And so I had like a therapist for these years that I was dating and I had a couple of people that I kind of went to as like mentors to just really help me.

I called it like the trenches of dating, like when you're actually actively dating and then you throw in online dating where there's like all these options and you go on a date and then the next day you see you go on the website and you see that the guy you went out with last night, also online right now, why is he online?

JW

It's so weird to me. So Audra and I met in college. I mean, I was I think it was 19 and like, we dated other people for a long time, but and so I don't think we became romantically involved until  maybe 23 or 24, but but it was like, boom, we're getting married. And here we are. This. Yeah. Like there was no if there was online dating in 1999 of the year 2000 or whenever, like I don't, I don't think there was. But it just it is the way things are now, but is it like is it worse? Do you think people actually had it better before the Internet?

SS

What's so hard to say? But I'm going to say, yes, they had it better. The options are so much more plentiful. And honestly, I met my husband online. So why am I saying this? But ha, it is brutal. It's just so brutal.

JW

And you said the trenches and. Yeah, it's it's trenches. Trenches and it's like, oh my God, that's like that is a World War one metaphor, you know.

SS

That's how I felt. I felt like I was emotionally getting beat up and it was really hard. And I was calling my therapist all the time like, what is going on? Like just all these weird things happening, right? Like you go on a date, you kiss a guy good night, then you go home. You're kind of butterflies and, oh, like thinking about what could be.

And then the next day you get like a pop up notification that someone messaged you and you go on the app and you see that they messaged you and you're like, Oh, but then you notice that the guy you just went out with online now like you could see that he's logged in and like what a mind f like you're like, wait, what it was I just remember being like, this is so messed up from the beginning.

So anyway, it was, it was pretty gnarly. But I, it also, you know, there's just anyway, there's so much to it. So I ended up dating a lot online, offline. I met people, I traveled for work, I was meeting people at trade shows and having long distance boyfriends. And in the end, like I was the go to girl.

First of all, everybody loved hearing my dating stories because I share I'm a sharer as you know. So, yeah, so I would be like, Oh my God, check out this crazy date. I went like, it was just comedic, you know? It was like I had all the good stories and then and I'm really open, so I'll share every detail.

And everybody was like, all over that. And then I got really good at dating. Like, it took me years of, like, therapy and practice and I got good at it. And so then people started sending me their friends like, Oh, Sophie, you need dating advice or you need help with your profile or whatever. They would send me people and then I started charging hourly for that on the side of like my regular job.

And I really enjoyed it and I was like, Yeah, this is cool. And then when I met my goal, it was like, Oh, she did it. Like then suddenly I got a lot of referrals and I really enjoyed it and I was like, It would be so amazing to have a career where I can, like, relieve the discomfort of this for other people and make it easier, just easier to navigate until you find your person, right.

And so I did the date coaching and then after I had the twins, I was like, in between jobs, I couldn't travel anymore. And someone posted, my cousin's friend posted that the matchmaker agency she worked at was hiring. And they were pretty small then. I mean, not small, but compared to now, it's like the largest matchmaking agency in the country.

So I got hired and I mean, within three months I had a couple engaged that I had set up and I was like, this is it. Like this is I love this. It was my jam. Yeah, it was cool. So. Yeah. So that you were hooked?

JW

Yeah, you were hooked. Yeah. All right. So transitioning into this friendship thing here, so I'm now curious as you've had a chance to reflect and I mean, this is kind of obvious, but I really like to start in the most obvious places. What is the difference between a romantic life partnership and friendship? Is it is it just sex?

I mean, if you if you take sex out of it, like, is it basically the same thing? What do you think?

SS

Yeah. So, I mean, I think sex, the physical intimacy is like the obvious main difference between the two. But even the way you approach it to like approach a potential life partner or romantic partner versus a friend. So when you go in to when you're meeting a new person, if your intentions are to date immediately, your mindset is like, Am I attracted to them?

Can I see myself spending my life with them? Like I was dating and I was like interviewing fathers and husbands really. And that's what my clients do too. And I'm like, Stop, stop doing that. But we all do it naturally. That's how you go into a dating scenario. Whereas when you meet a new person without any.

JW

So when you said that you interview fathers and husbands, do you mean you're interviewing this person for the role of. Yes and yes, yes. Yes. Right. And so that would be a big difference because when when you are getting to know somebody to see if they're going to be a friend, you don't have them pegged in like, no, you're going to be a friend who does this with me or you're going to be that friend, or you're just like, let's hang.

SS

Right. But it puts so much less pressure on the connection. And I try to encourage my clients all the time, like let go of the outcome. Like, I know I'm setting you up on a date, but like just see if you want to hang out with this person again. Like go in as if you're maybe meeting a friend, a business partner, who knows, right?

There's so much pressure when people go on a date and then there's like they're they're like, oh, my God, is there a spark? Am I attracted to them? You don't think that when you meet a friend at a party, when you get you know, like if you're talking to a new person, you're not like, oh, like, do I want to take your clothes off? Like, I might, you know, like, there's just none of that usually.

JW

So you take out the physical. Yeah, the physical part of it. And then but this other part is really similar. You're thinking, do I want to spend more time with this person?

SS

Like, do we want a second date? Yeah. Like I tell people, the purpose of a first date is to find out if you want to go on a second date. It is not to find out if this will be your future husband, wife, parent of your children. None of that. I mean, and that's so but but when you take physical intimacy, I think what happens is like when two people meet, right.

And they could have just been friends. But then there's the physical connection and there's some sort of a hookup. Right. Happens. All what this does is it adds this new layer of feelings. And the feelings come from a physical, logical process. Right? Like there's this amazing hormone that I love to talk about called oxytocin. And oxytocin can really mess us up.

I mean, especially women. Are you familiar with oxytocin and all the wonderful things that does?

JW

And hugging, bonding hormone? Yeah.

SS

Yup. And women tend to release a lot of oxytocin, much more than men actually are. We produce a lot more and we release it a lot, a lot of it when we're breastfeeding our children and also when we have an orgasm. And so and men do, too, but women and so this creates this like extra layer of feeling and attachment that feels very real.

And then suddenly there's like new rules around and reactions and emotions around this new connection, right? So if you meet someone, you hang out, you have dinner, you have a great night, you say good night. Bye. And they don't text you the next day. You're not probably even thinking about it much. Like maybe you're like, Oh, I would like to hang out with that person again.

But if you hooked up that night, the next morning, if you are women especially, but men also. You are. You've got that phone out. Who's going to text? Who are they going to text me? Am I going to see them again? Oh, so much starts happening, right?

JW

Yeah. So automatically I'm hearing this, there are levels then when we're talking about romantic relationship. So if you just go out on that first date and you just talk, you have a good time. Nothing happens beyond that. And so you're you're out like maybe just the first level. Like, I don't know, friendship. Yeah. You know, we'll, we'll like, we'll see if we, you know, connect again.

And then the next level up is like, okay, well, if we hook up, you know, then, then we're on to now another level I would imagine. I mean, I, this world is so, so far in the past for me, I'm imagining at least one other level before life partnership. We're together forever. But there are these levels to romantic relationships.

And so I'm curious if you see these same levels in friendships. I mean, yes, like we know like. Okay, that's an acquaintance and that's a really good friend. Do you see the same thing?

SS

Yeah, I think. But what's cool, yes, there are obviously different levels of friendship and also but but the best part about friendship is that they're so much more fluid. So it's really hard in romantic relationships to go back a level you can't. It's really hard to backpedal. Like really hard.

JW

Oh, I haven't thought about that. Yeah.

SS

Yes. So, so when you make a new friend or even with friendships that I've had my whole life, oh my God, there's such an ebb and flow to those friendships or even the friendships I've had for the last five years, nine years, two years, five months. It doesn't matter. It's like there's just this ebb and flow and both people can show up as much or as little as they want to or can, and that like like the parameters are. So there's just so much more elasticity to it.

JW

That's fascinating. So yeah, though that that yeah. So you can't go back in these romantic ways. And that's why when, when there's a divorced couple and we hear that they're still friends and that like everything's cool and they can still hang out, like that's mind blowing. Like what? Because. Yeah, and that's because of this assumption. Like, you just can't go back, love.

SS
Well, yeah. And that becomes really complicated too, because, you know, parents, single, you know, divorced couples who have to they have to co-parent. Usually you would hope that they are right and a very close warm amicable co parenting relationship is really like ideal for the kids. Right. And every everybody really. But then you have these people who are dating and meeting new partners and then the new partners are like, wait, they're like so close with their ex.

Like this feels threatening and so I, I just feel like, I think that as adults and as parents, I think it's just important not to put so much pressure on our, our husbands, wives, spouses, life partners to give us all of that, that friendship. Right? Like we can't get it all from one person. The rules are set for our life partnership.

Okay? Like you've hooked up a ton. You're married, you've got kids. There's like, all these. I mean, that's really has very little flexibility, to be honest, you know, and so I think that's why having friendships as an adult, as a parent outside of your home life partnership is so important. It really is.

JW

I just I just remember one of the really great quotes from the podcast that we released at the beginning of August with Blake, and she says that she thinks about friendships as living organisms. and I love that because like you really, you cultivate it, you nurture it. And, and, you know, like things change. There is this like developmental arc. But I would I have to think that romantic partnerships are also living organisms like they are. The other thing that they have all these rules and they're more structured.

And so I was thinking, okay, what's the difference between these living organisms? And I don't know, this just popped into my head. The romantic relationship is the living organism where you're like, this thing has to bear fruit, like, because this is what I, I'm going to need the fruit to survive. Like I'm going to need the fruit too.

Like, yes. So it's like, oh my God, like, I cannot mess this thing up. But then the other friendships can kind of come and go. It's like, you don't need a flower, you don't need to produce any fruit. Maybe sometimes you will and maybe sometimes you won't. But it's like.

SS

I love that. That's really great. Yes, I love that. That's true. I think it's like that our life partnership should be where we put the most kind of focus and energy on nurturing. Right. And the nice thing is that the more connections you have outside of that, the less kind of pressure there is right to like make everything at home feel perfect if you have if you're if you're getting your emotional needs met in multiple different ways.

Right, because one person can't do it all, you know. Right. Yeah. So, yes.

JW

Yeah. That's that's a that's a big thing. I in previous academic life, one of the things I love to study was this transition, like basically this transition from old world traditional communities to these modern societies that we now live in. And that if we, we can we we can actually trace the history of love and like like the history of paired partnerships and that they used to be part of these large social networks, you know.

And so we wouldn't expect all of our needs to be met by just one other person. But then the world comes along. And in these modern societies, like, Oh my God, now all everything I need in life is put on to this other person. So, right, I'm imagining now that this is probably a really big reason why friendship is so important. Like, is this the key for you?

SS

I think it is, honestly. And I, as a matchmaker, I mean, look, obviously, my clients hire me to find them a romantic partner. But oftentimes I watch these connections unfold as friendships and those have happened to me also. So I have a lot of friends that I made over the years that started as a first date.

JW

So do you have any friendships where things get really serious and then you were able to pull it back to friendship because that is what you mentioned before you like. It's really hard to go back.

SS

Okay. Those friendship. Yes, I'm still friends with men I actually dated, which my husband and I laugh about all the time. Like he'll meet someone and be like, Has he seen you naked?

Maybe, maybe not. I don't know. We're cool. Like, he has his own list and I have mine, so we're cool. Like, it's all good. Like, we're like we neither of us are bothered by it, but so yes, I happen to be, but I'll tell you, those friends are not they're not people I'm friends with, like talk to on a very regular basis, but they're still like, we're in each other's lives.

We hop in and out when it feels right. We're connected. I mean, look, Facebook, Instagram, it's just so easy to stay connected, very loose, like on such a surface level.

JW

Okay, so that's a good yeah. I think just because we, we earlier we mentioned how the online situation just being online social media everything has affected the dating scene. How do you think it's affected friendship?

SS

Oh, honestly, I think it's actually amazing for friendship. I, I love it. I encourage parents. So like I said, I'm so lucky that I have friends still that I talk to every day almost for like 39 years. That's very unusual. But I think that a lot of times, like I've had people reach out to me on Facebook or I've reached out to them just because I felt this like, Oh, I saw a post from like an old friend.

I'll just send her a message because that really touched me. Not a public message, like, not a comment, like a direct message. And then suddenly we like this, like we rekindle this little connection, and then sometimes that turns into something really seasonal but amazing. And so I think that a lot of times people are insecure about like, oh, I would love to reconnect with that person.

Like, do it. There you go. It's so easy. You're hiding behind a computer screen and you never know. Like, you might just reach out and, like, have this. This like a new spark happen again, right? With, like, an old friend and get on a face time and then end up planning a trip to see each other. If you don't live in the same place, or sometimes people will move from with another, like let's say you grew up with somebody and then they live somewhere further, like somewhere else.

And then you realize that they moved back. Hi, like go grab coffee or say hi. I think it's so hard for working parents and just all parents to create and, you know, create friendships and also meet new people. You can also go back to connections that you've had from so long ago. And I think Facebook is a really great way to do that or Instagram.

JW

Well, that's really yeah, the connections that we had so long ago and then reconnecting with those people. I've had this experience as well. It's like, Oh, we were like really good high school friends and then we lost track and then, oh, now we're connecting again and it's almost like this instant, like we can just pick back up. Yes, but making a new friendship at like I'm 45 years old, making a new friendship today.

Well, with you, Sophy, has been just a breeze. But beyond that, you know, it's like it's it's more challenging. And so what do you think makes it so different? Like, why is it so much easier to make friends when we're kids and and teenagers than it is to make friends as adults?

SS

Oh, God. Because kids are just so Zen like moment, like, in the moment, like, oh, cool. We're like playing the same, like, video game right now on our phones, like, whatever, right? Like, I watched I watched Audrey the other night. Sit down next to my friend Sydney's son, and suddenly, like they had never met before, they were playing war with cards.

We're like, Here's a deck of cards. They just went at it. Like, I was like, Oh God, this is so awesome. Like, it's so hard to even they're playing because they're playing and as adults we don't play that much anymore. We're just like, our brains are so like going.

JW

Okay, so that, okay, what, what just popped into my head as I'm thinking. Absolutely. I totally remember that being in elementary school and how much easier it would, how easy it was to make friends be like, we're just going to go out on the playground and play soccer together. Or, you know what? It's just, boom, we're all we're all together.

And there's this play. But then, of course, middle school comes along, things get often it's weird and hard and I remember that that that's how I felt. And then on into high school and you know, I connected with some friends. What I'm about to say, though, I want to say parents, if you're listening to this in the car and you don't want your children to hear anything about about ex, if you don't want them to hear things about high school that you would rather than not.

So one thing that I'm realizing is one of the reasons I really got into smoking cannabis. I call him cannabis now to be proper you. Yeah we I had ever in high school is that it was like an instant way to connect with other it totally it was like okay basically what toys and playing were when when I was a kid it was like, oh, you smoke weed I smoke weed.

We can hang. And then boom, the walls come back now and now we're connected and boom. My social network expanded so much because of like oh minded too.

SS

I mean, weed and alcohol were just wonderful for that. Like, yes, all the walls come down like all the like, you know, the anxiety, the social anxiety, the neuroses, like all that.

JW

Well, it does also have have. Yeah. So that stuff comes down. But it was always just like the simple act of just. Oh, yeah, just like, oh yeah, doing something together. And this, this is connected.

SS

Here. Hit this, hit this. Yeah. Hey. Yeah.

JW

Well, that's another thing. Yeah. So now as a as an adult, as a parent, I imagine if I developed a, like, regular cannabis habit, I might be able to expand my friendship again. But outside of that, I don't know. I don't know how.

SS

That's going to like, effect your productivity now.

JW

And I don't know exactly, but it does help me to reflect on maybe why it might be harder to make new friends as an adult. So, Sophie, how. Yeah. Can can can you, can you speak a little bit about this? How so? Well, let's just let's just start. Start here. How do you make new friends otherwise? What is your way?

Like, how do you do it for yourself? So.

SS

Okay, so I was thinking about it before we did this. Like the friends I've made as a parent, like new friends, right? That came after I had children. And it's really hard because our free time shrinks to basically nothing at first. I mean, it’s so precious. You just don't you're like, I don't want to spend any of my free time with anyone unless this is like the shit. Sorry. Like, it's just you can't even. It's like gold. It's like it's just you're so and I'm so picky about it. And and to be honest, this really does parallel with what I do for people for a living.

I mean, these people are like busy executive, single parents running their businesses. They're paying me for that time to like find people, meet them, sort through them, and then just give them like the nuggets like that are really good potentials, but you can't do that with friendship. So I encourage, like I found that like my best friends and really like to today I would say to date I have like probably one really, really close friend that I made after my kids were born.

Like, maybe more. But my friend Kim comes to mine and she was just here yesterday. Her twins and my twins went preschool together.

And so we would sit on the playground and talk and just. Just shoot the shit. Like, we would be like. Okay. And we became. Well, it didn't obviously help that Sasha and Audrey and Lillian, they were just like more like happiest together. But we really like, really liked each other. And she would ask me for dating advice because I'm a matchmaker.

And I was actually there at the day she told me about her first date with her husband that she just married two weeks ago. So that was seven years ago. So it was just and what I what I'm getting at is, if possible, when your children are young and you do supervised playdates, where it's a playground or it's someone's house, you don't just drop off a four year old at someone's house.

You're there with the other parent. That is like a really good time to screen them as a friend. Right? I call it screening and matchmaking. I'm going to screen this match for you, but it's just a little kind of forced together time. But it's limited. It's like a first date. You're like your kids are playing and you can chat and.


JW

It has this, well, I like to use the word like instrumental. So it's like, we're not really doing this because we're screening each other, right? Because we need to supervise our kids. And so super low stakes that it like like I have no obligation to reach back out to you. You have no obligation to reach back. Right. So it's like as low stakes.

SS

Absolutely. Exactly. So there's just no pressure and you could get to know and then and then like if things are jiving, you're like, okay, like this could be a front again. It all goes back to letting go of the outcome. Like, I'm like when you're not focused on the outcome of a human connection, I think it just allows things to just organically unfold however they're going to unfold.

And so and it's nice look, but not all of us have little kids anymore. So look, my my twins are nine now. I mean, the other day, I had a mom approach me at camp who was like, hey, our girls really like each other. Can I give you can I get your number? Like, I want to do a playdate with that? And I was like, whoa, this is moving like really fast. What's my number?

JW

Yeah, like, that's the equivalent of like, like kissing before we've even gotten ach other's names. Yeah.

SS

It was really like, whoa. I was like, this is like we just jumped to second base right away, but yeah. Slow your roll. Exactly. And it does get awkward also, I think like sometimes when our kids make friends and then you're like with the other parents or you're at a birthday party or whatever, and then like other parent, another parent is like, Oh, we should get a, we should do a double date, you know, and I'm in my head thinking.

JW

There is no way this woman do that. Okay. So I've, I've two things. First, I'm like if I think of people on a spectrum, yeah, a whole continuum of like people are just naturally super social and boom, boom, they're out there. And then people who are more introverted and quiet and to themselves. So if I think you are on the far end of the more social spectrum, like you are like I am, you're you're out there, you're connecting, you are an actor.

That's why you're such a good executive matchmaker. But I want to like slow down just a little bit and recognize that for a lot of people who are going to be on the other end, who are going to be more introverted, are going to be much more maybe in their heads about that interaction of, yeah, how do I approach another parent?

How do I know? Like they might be the the parent who, who goes too fast because they're like, I don't know how to like, you know, how do I approach that? Like, I think I might be friends with this person or I could be I could see myself becoming friends with this person. So I'm going to ask and see if they want to go on a play date with our kids.

What advice do you have for that parent who is more introverted and is like looking for ways to connect and is afraid of moving too fast?

SS

Don't move too fast. Just think of like a really like ask them on a first date. So, so first parent, mom, dad date. I don't know. To me that is like, like, first of all, if your kids are young enough to do the play date, that's a perfect go to like, let's do a play date. That's a no brainer.

Again, that goes back to like, we're just doing this for our kids and then you can see how that goes. So but for those of us who have older kids, like I dropped Sasha off on that playdate, I wasn't there. I mean, I was just like, good luck. You seem cool. Yeah.

I was really kind of rolling dice there. But but no, but like for people who have older kids, like, you know, nine, ten, 11, whatever, and they're there, but they're like noticing that there is another parent that through the school or wherever or through activities that the kids do. I mean, you can do a couple of different things.

So first of all, you could do something really low pressure like, Hey, we should grab coffee sometime or Hey, after drop off, do you want to like grab coffee or something? A little lower stakes than we should get a glass of wine or we should go out in the evening evenings to have more pressure in general. And by the way, as a matchmaker, I actually highly discourage coffee dates because they're so horrifically unsexy and unromantic.

And so they feel more like a very platonic or even interview. So I'm just like, those are perfect for like and again, you have to think about whether that parent works. Maybe they drop their kid off and go right to work, whereas others don't or have more flexible. I've had people approach me and be like because they know that I go for walks after drop off some time.

Like if you both if like just find something that, you know, maybe the two of you have in common, right? Like if you're both people who probably work out like, hey, do you want to go for a like drop after we drop off our kids or whatever? Like go for a quick walk or a hike or like I said, just really low pressure. Coffee is just so easy. It's just.

JW

Real. Yeah, I'm going to do all this because I. This is just sticking in. My brain went to be good. Okay. Sorry for the romantic matchmaking sphere for a new so people that you're connecting for the first time if they do go out on that coffee date because it's so unsexy and so and romantic that then if there's a connection in that context, then boom, you've you've hit gold.

It's kind of like a way to really see, like, okay, the, like, take, take away all the other stuff is, is there a connection?

SS

You're challenging me. Because I really hate coffee dates for four dates. I guess you're right. Like, I'm actually being like, I'm contradicting myself because I'm telling you, let go of the outcome. Go in. Like you're meeting a new person, a friend, but also coffee dates are really not sexy and romance. They don't just don't lend themselves like there's just and honestly, I'm not I'm not like hard core. Like there are certain people who I match who I actually think do need to go on more of a coffee smoothie non standard date but remember these people are paying me a lot to achieve the romantic outcome.

JW

And so throwing them into just a Starbucks and a like egg like. Right, that's not Starbucks. Broad daylight.

SS

Caffeine. You're drinking caffeine. And you're just like, it's so nerve wracking to go on a first date. A coffee can really like, really exacerbate nerves. People interview for jobs at a coffeehouse like.

JW

All that, all that. And yeah. So I am affirming you or your choice there, but just that thought came up as like if in all these barriers a connection is made, then you know, yes, the goal like I have yet.

SS

I mean I have yet to see to have matched a couple successfully where their first date was a coffee date. So and I've sent out over 1500.

JW

Yeah, yeah. Right, right. It's A lot. You, you have some experience there. Yes.

SS

Yeah. So I don't know. It's just but but for friendship and for parents, it's awesome. And it's just I love it. Like, I love that idea and it's just like super low pressure. The other thing that kind of comes up for me though, is when another parent approaches me, right? Or maybe you're more introverted parent, right? And a person and some crazy extrovert like me comes over and is like, Oh, we should like, let's go for a hike or whatever.

And you're like, Wait, I don't know. It feels it could be like really uncomfortable in that moment because it's really hard for people, even extroverted people like me, to be honest in the it's really hard to like reject someone, right? Or like, God, it's so hard, so hard. So I thought about this and like I give this type of advice to all my clients who go on dates and at the end there's the so like, we should do this again.

I had a really good time and like, how do you respond if you're not sure, right? Or whatever. So I would say, like, if you're that kind of a little bit more like introverted person and you're being approached by a very outgoing person like me, I think like a really nice way to respond is to give yourself a, like, more time, right?

Like, Oh yeah, that could be fun. Let's text and see what, like what we can arrange over the next few weeks. Few weeks. That's like plenty of time. There's no, like, pressure. Not like this week or tomorrow. And then you can go home and think about it and decide and then like move slow. So I just kind of wanted to put that out there.

Yeah, because it's really hard sometimes for people and even for me sometimes, you know, to be like, No, that doesn't actually sound like something I want to do right now. Like, I'm too busy a new person. I don't know you well enough, you know? So, yeah. So that, that also kind of popped in my head as I was thinking about parent dating and friend friendship dating in the parenting world.

JW

I want to also talk about breaking up. And so I don't know. Now you're not I imagine you don't have really you're not there for the romantic breakup. You're there to put people together.

SS

No, I'm there for you. I'm there for both. Oh, no, no, no, no, no, no. I'm there for some a lot. Oh, yeah. Because I mean, I imagine a lot of people who will date and then they'll date for two or three months and then realize, all right, like, okay.

JW

Okay, there's a lot.

There are sometimes friendships where it's time to break up. I mean, if it happens. So, yeah, how can you help us think about letting go of a friendship when that time has come?

SS

Well, first of all, it's like deciding right for yourself. Like, is this friendship serving me anymore? Like what? What is. What's what's going on here? I found this happened to me in my life multiple times. Where I a couple times where even somebody that I knew from when I was in college, you know, and we had been like best friends.

So actually it happened with my roommate, one of my roommates in college. We lived together for four years in our lives. Just took these like really different paths. And she moved to San Diego at some point and just was like suddenly integrated with my friend group. Or I was obviously like, Oh my God, you're in San Diego. Like, Let's hang out and it didn't work well.

Like it was just like really uncomfortable for her. For me, she felt a lot of like it was just it just wasn't a fit at the time. We were in like really different places in life and eventually it hit like a breakup. And I think we were just like, like at that point, this is like with a history with someone, right?

Like we had to like have an honest conversation about it and it was more just like, listen, like this is not working like ever. Like, I don't feel good when we interact, when we talk. But I don't think that most friendship break ups happen that way. That was like a very honest, raw, long term one. I think sometimes honestly, things just fizzle.

Like, Have you ever had that happen?

JW

Well, that's that ebb and flow. And right where there's just an ebb and it never flows again.

SS

Exactly. And I think I think you need to just think about what a friendship, how that friend makes you feel like. How do you feel when they when you even get a text from them? And I actually just it's funny enough, I just had a conversation I think yesterday or the day before with a girlfriend of mine. I think I even told you about it, Justin, who went on to tell me, Oh, I'm having I'm going to an IFS lecture tonight like we had actually not, we've known each other since we were very little.

She's part of that crew, the Jew crew and we had really like drifted apart. And that was conscious on her part for the last few years. And yesterday or the day before we talked and she told me, I've just pulled back from you because I felt judged. I felt like you were always trying to fix my single hood.

My I mean, it was really and I actually knew it deep down inside. I knew it couldn't help myself with her before and then. Now it just it was pretty rad because we had this, like, amazing conversation. And I almost feel like we just got back together.

So I think you just need to decide. And that's what she did. She decided it for herself. I was reaching out to her all the time and she was like, Aha, aha. Like she was blowing me off as a friend and I didn't push because I kind of knew I'm like, This isn't she's not down for this right now.

And I think we just all need to be aware of like a, how we feel in a friendship and when it's time to sort of back off or let them back off, you back off, whatever it is, right? Yeah. So that's kind of my.

JW

Thought on that mean last friendship question and never will go into our our final three. Mm hmm. Well, I want to just briefly talk about being a parent and being friends with other parents. That makes sense. But being a parent and being friends with non-parents there feels to me like there's a gap there. Like I can think about my non parent friends and we're like we're friends.

But it's like there's something, we're like, you don't really get my life because being a parent is so radically different way. It just changes everything. So I'm curious, first off, do you have any non parent friends who are like super, super good friends? Yeah, I do. Oh I was. I did.

SS

Again, it's going to parallel a parallels to dating also and I'm I'm doing this because I'm so matchmaker Sophie talking here this is such a catch 22 in dating because single parents are like, oh my God, I like, I want to meet somebody who gets it, who gets the, like, all consuming existence of being a parent. It's just all consuming.

And you're like, Oh, I just want somebody. And then but then the problem is, and I think this problem comes in also with adult with with parent friends, right. If you were at the mercy of our children's schedules, activities, illnesses, medical emergency, medical conditions, I mean, yeah.

Just throw those some big medical conditions in the mix. I mean, suddenly you're like, when can and then the other parent has their things. And that happens with dating too. It's like, sure, we get each other and when we're together and connecting there is so that understanding. And so there's this like bond and understanding and connection that happens between two parents, both in dating and friendship, but logistics.

It becomes really logistical sometimes, and it's almost difficult to make time or for them to make time and you guys to have the right times line up, to spend time together, talk to each other, even on the phone right. Okay.

JW

So I just realized that I that I have this because I do have several really good non parent friends like just dear, dear, non-parent friends and just realize I carry this silent suppressed judgment any time that we're trying to connect and their schedule is somehow blocked off. And I'm just like, what are you doing? Like you have kids, you do not I I'm sorry.

Whatever is how I do that. Your life I guess that's juggling like I do that you should be able to fit into my schedule right.

SS

And that's we have to be careful as parents not to do that. I do the same thing. So I have to I would say to really close friends both from college who are like two of my best friends. I know I say that about a lot of people just end, but they are there's like a very. Yes, trust me, if you ask them, they're going to say the same thing.

So but they're both from college and they're both unmarried with no kids. And there's just something so great about connecting them. And suddenly I'm not just talking about my kids the whole time. Suddenly I am Sophie. Pre-mom Sophie and it's awesome. It's amazing to be able to just reconnect with like who we are, the parts of us that aren't a parent, like we're not, you know what I mean? Like who we were before we were parents and just it when I am with my friends, we talk to the ones that are married with kids. Like we talk about our kids and our husbands and our wives and our everything.

Like, it's just like those conversations just keep happening. It does. It's, like, impossible to get away from them. But it's so fun to sit down with somebody who isn't all consumed by that. And then suddenly you're like, Oh my God, there's this whole other part of me that I miss. Yeah. So I think it's important and nice and I really, I really enjoy that. But I do the same thing, by the way. I'm like, What? You're busy. Like, what in God's name could you be doing right now?

JW

It's like, I love, Oh, all right. So at the end of every podcast, we ask our guests these three questions, so we just roll. Rotherham Just and I love how we can compare how each each guest answers these. So the first one is Sophie, if you could put a giant Post-it note on every parent's fridge tomorrow morning, they wake up, boom, the post-it note is there. What does it say?

SS

Okay, this is going to sound like kind of generic, but it's just it's what I came up with. You can do hard things.

JW

Right? You're tired, you're exhausted. Your kids lunches need to be made. Everybody. The lunch closed and out the door. You can do it. And then after running that gantlet, then you have to go to work and you can do it. Yeah. So Sophie, is there a quote recently that has changed the way you think or feel?

SS

Okay, so I thought about that. I mean, this didn't change the way I think or feel, but it definitely ever since I saw this quote, it like fully embodied my experience as a parent and as like a human in general. It's the real quote. Let everything happen to you, beauty and terror. Just keep going. No feeling is final.

JW

And then finally, what is your favorite thing about kids lately?

SS

I've found that my favorite thing is I love explaining to kids these cons that's in life that are so mundane to us as 45 year old grown ass adults like something as simple as like, I don't know, just like medical insurance. Like they look at a bill and they're like, What is this? And I'm like, Oh, this piece of mail. Here's what's on it. Like, here's how this works.

Here's the medical bill, or here's even like a power bill, whatever. Just like that sense of like the ability that if you kind of just really get into the moment with kids like be present, you can kind of relive that, like, sense of wonder, terror and newness that we just you lose as you get older and live more years, you know?

In this episode

On this episode of the Yes Collective Podcast, we talk to executive matchmaker and mom Sophy Singer. She finds life partners for CEOs, lawyers, and brain surgeons, and on this episode she's bringing her years of experience to the world of friendship. We talk about why it was so much easier to make friends as kids, whether parenthood makes it harder to find really good new friends, how we can find really good new friends in adulthood, how we can nurture these friendships, and so much more. Tune in to hear us dig deep on friendship with the amazing and wise Sophy Singer.

Listen here

Listen on Apple Podcasts, Spotify, Stitcher, or Overcast

About our guest

Sophy Singer is an executive matchmaker and founder of Sophy Love, a boutique concierge matchmaking agency. She started her career in matchmaking in 2010 as a dating coach, and found she had both a passion and knack for mentoring people to become their best selves as they played the dating field.

In 2016, she took a leap of faith, quit her job and joined the largest matchmaking firm in the nation. After countless engagements, marriages and babies born as a result of her matches, however, she wanted to get more personal, so in 2018, Sophy branched out and launched her own agency. At Sophy Love, she is able to bring her bubbly, intuitive and unparalleled charm and optimism to every single client. Her service is personal and personalized, and her results speak for themselves.

Transcript highlights

Justin Wilford (JW)

So, Sophie, I do want to start this podcast though, by just surfacing the fact that we are friends that like so we have friends on the podcast, but many of our podcast guests are just experts, therapists, mental health professionals that we bring on. And they share their wisdom with us. But Sophie, we are friends and we are fellow childhood cancer parents. So we have these connections. And so I just want to just like bring that to the surface that this is a conversation among friends. All right. Yes. All right. So let’s do it.

So, Sophie, this month in the Yes collective, the theme is about emotional health and friendships. And so I thought it'd be really awesome because one of the things that we're dealing with throughout the month is how do we make friends, keep friends, maintain friendships as parents. Now we have our lives are full. We are now grown. Well, we're grown ass adults and so how do we do this? And so you came to mind because you are an executive matchmaker. So you help people come together, but of course, for romantic life partnerships. But I thought, oh, maybe Sophie has some wisdom around the friendship thing. So first, you know, I'm just going to ask right after the beginning. Right at the beginning, how do you feel about talking about friendships?

I know your specialty is about romantic matchmaking. Are you okay with this? Like, how do you feel?

Sophy Singer (SS)

100%. Okay. I actually feel like I'm a major expert on friendships, too.

JW

Okay, so. Sophie. Yeah? I have known you. Like, I feel like I've really gotten to know you. Well, maybe, I don't know. Three months or something like you hasn't been at home and already. I do feel like we're really good friends. I'm just like, Oh, Sophie, where else? But I can assure you have like a you have so many friends.

SS

I have a lot of friends. I was thinking about it actually today and I was thinking about it in reflection of listening to the last podcast you guys put up about friendship. And I honestly, I'm very lucky and honestly privileged to have grown up in one place. Basically my whole childhood. We didn't move around, right? We were in San Diego, but like we moved to different parts of San Diego.

But like I was in San Diego from when I was, I don't know, three or four or five. And then we did not move. That was it. And so when I was like six years old, my parents sent me to this Jewish school, San Diego Jewish Academy, and my kids go there now and like I have this group of friends and we just stayed friends.

I mean, it was like all the way through high school. I went to college with some of them. I went to college with Tammy. I mean, most people do not have that. Like I would say, majority of people do not have that. And so we do have this really special group. And again, maybe we've stayed together all these years because we were lucky enough to be together all the years, and we've been together through one another's traumas and all sorts of life events.

But yeah, I do have a lot of friends, but I've always loved making friends everywhere and I'm still really good friends, like best friends with like a handful of my college besties and then work and that, I don't know, I just keep gathering them.

JW

So it's not your profession and expertise, but you do have a natural expertise around friendships.

SS

So I do, I do. But it really the more I thought about this going into this podcast, friendship, platonic friendship as adults and dating really have a lot of parallel.

JW

All right. So let's get into it first. I would love to know, how did you even get into this? This is such a unique field. When I first heard that this is what you do for a living. Like, my mom was like, what? Oh, I thought that was only in the movies. I but yeah, this is a real thing.

SS

Yeah. And my husband always says whenever I say my wife is a professional matchmaker, he's like, Jeff Bezos could be in the room and everybody will just turn and be like, Wait, what? Tell me about it. And people are like, oh, you do that for a living. Like you make money. And I'm like, Yeah, that's my job. So it happened. I was just kind of called to it through my own life experience. I broke off an engagement in my late twenties and I was kind of back on the dating scene, full blown, like looking for a husband and like a baby daddy.

I was like, I need to get married, have kids, because that's like the next thing. And most of my friends were already married and starting to have families by then. And so I was like really behind. And then I had to do online dating and that was kind of a trip. And so I had never dated before really.

I had just had like a handful of like serious boyfriends. So dating was really difficult emotionally. I mean, it's just a roller coaster and it can like really mess you up. And so it was hard. And so I had like a therapist for these years that I was dating and I had a couple of people that I kind of went to as like mentors to just really help me.

I called it like the trenches of dating, like when you're actually actively dating and then you throw in online dating where there's like all these options and you go on a date and then the next day you see you go on the website and you see that the guy you went out with last night, also online right now, why is he online?

JW

It's so weird to me. So Audra and I met in college. I mean, I was I think it was 19 and like, we dated other people for a long time, but and so I don't think we became romantically involved until  maybe 23 or 24, but but it was like, boom, we're getting married. And here we are. This. Yeah. Like there was no if there was online dating in 1999 of the year 2000 or whenever, like I don't, I don't think there was. But it just it is the way things are now, but is it like is it worse? Do you think people actually had it better before the Internet?

SS

What's so hard to say? But I'm going to say, yes, they had it better. The options are so much more plentiful. And honestly, I met my husband online. So why am I saying this? But ha, it is brutal. It's just so brutal.

JW

And you said the trenches and. Yeah, it's it's trenches. Trenches and it's like, oh my God, that's like that is a World War one metaphor, you know.

SS

That's how I felt. I felt like I was emotionally getting beat up and it was really hard. And I was calling my therapist all the time like, what is going on? Like just all these weird things happening, right? Like you go on a date, you kiss a guy good night, then you go home. You're kind of butterflies and, oh, like thinking about what could be.

And then the next day you get like a pop up notification that someone messaged you and you go on the app and you see that they messaged you and you're like, Oh, but then you notice that the guy you just went out with online now like you could see that he's logged in and like what a mind f like you're like, wait, what it was I just remember being like, this is so messed up from the beginning.

So anyway, it was, it was pretty gnarly. But I, it also, you know, there's just anyway, there's so much to it. So I ended up dating a lot online, offline. I met people, I traveled for work, I was meeting people at trade shows and having long distance boyfriends. And in the end, like I was the go to girl.

First of all, everybody loved hearing my dating stories because I share I'm a sharer as you know. So, yeah, so I would be like, Oh my God, check out this crazy date. I went like, it was just comedic, you know? It was like I had all the good stories and then and I'm really open, so I'll share every detail.

And everybody was like, all over that. And then I got really good at dating. Like, it took me years of, like, therapy and practice and I got good at it. And so then people started sending me their friends like, Oh, Sophie, you need dating advice or you need help with your profile or whatever. They would send me people and then I started charging hourly for that on the side of like my regular job.

And I really enjoyed it and I was like, Yeah, this is cool. And then when I met my goal, it was like, Oh, she did it. Like then suddenly I got a lot of referrals and I really enjoyed it and I was like, It would be so amazing to have a career where I can, like, relieve the discomfort of this for other people and make it easier, just easier to navigate until you find your person, right.

And so I did the date coaching and then after I had the twins, I was like, in between jobs, I couldn't travel anymore. And someone posted, my cousin's friend posted that the matchmaker agency she worked at was hiring. And they were pretty small then. I mean, not small, but compared to now, it's like the largest matchmaking agency in the country.

So I got hired and I mean, within three months I had a couple engaged that I had set up and I was like, this is it. Like this is I love this. It was my jam. Yeah, it was cool. So. Yeah. So that you were hooked?

JW

Yeah, you were hooked. Yeah. All right. So transitioning into this friendship thing here, so I'm now curious as you've had a chance to reflect and I mean, this is kind of obvious, but I really like to start in the most obvious places. What is the difference between a romantic life partnership and friendship? Is it is it just sex?

I mean, if you if you take sex out of it, like, is it basically the same thing? What do you think?

SS

Yeah. So, I mean, I think sex, the physical intimacy is like the obvious main difference between the two. But even the way you approach it to like approach a potential life partner or romantic partner versus a friend. So when you go in to when you're meeting a new person, if your intentions are to date immediately, your mindset is like, Am I attracted to them?

Can I see myself spending my life with them? Like I was dating and I was like interviewing fathers and husbands really. And that's what my clients do too. And I'm like, Stop, stop doing that. But we all do it naturally. That's how you go into a dating scenario. Whereas when you meet a new person without any.

JW

So when you said that you interview fathers and husbands, do you mean you're interviewing this person for the role of. Yes and yes, yes. Yes. Right. And so that would be a big difference because when when you are getting to know somebody to see if they're going to be a friend, you don't have them pegged in like, no, you're going to be a friend who does this with me or you're going to be that friend, or you're just like, let's hang.

SS

Right. But it puts so much less pressure on the connection. And I try to encourage my clients all the time, like let go of the outcome. Like, I know I'm setting you up on a date, but like just see if you want to hang out with this person again. Like go in as if you're maybe meeting a friend, a business partner, who knows, right?

There's so much pressure when people go on a date and then there's like they're they're like, oh, my God, is there a spark? Am I attracted to them? You don't think that when you meet a friend at a party, when you get you know, like if you're talking to a new person, you're not like, oh, like, do I want to take your clothes off? Like, I might, you know, like, there's just none of that usually.

JW

So you take out the physical. Yeah, the physical part of it. And then but this other part is really similar. You're thinking, do I want to spend more time with this person?

SS

Like, do we want a second date? Yeah. Like I tell people, the purpose of a first date is to find out if you want to go on a second date. It is not to find out if this will be your future husband, wife, parent of your children. None of that. I mean, and that's so but but when you take physical intimacy, I think what happens is like when two people meet, right.

And they could have just been friends. But then there's the physical connection and there's some sort of a hookup. Right. Happens. All what this does is it adds this new layer of feelings. And the feelings come from a physical, logical process. Right? Like there's this amazing hormone that I love to talk about called oxytocin. And oxytocin can really mess us up.

I mean, especially women. Are you familiar with oxytocin and all the wonderful things that does?

JW

And hugging, bonding hormone? Yeah.

SS

Yup. And women tend to release a lot of oxytocin, much more than men actually are. We produce a lot more and we release it a lot, a lot of it when we're breastfeeding our children and also when we have an orgasm. And so and men do, too, but women and so this creates this like extra layer of feeling and attachment that feels very real.

And then suddenly there's like new rules around and reactions and emotions around this new connection, right? So if you meet someone, you hang out, you have dinner, you have a great night, you say good night. Bye. And they don't text you the next day. You're not probably even thinking about it much. Like maybe you're like, Oh, I would like to hang out with that person again.

But if you hooked up that night, the next morning, if you are women especially, but men also. You are. You've got that phone out. Who's going to text? Who are they going to text me? Am I going to see them again? Oh, so much starts happening, right?

JW

Yeah. So automatically I'm hearing this, there are levels then when we're talking about romantic relationship. So if you just go out on that first date and you just talk, you have a good time. Nothing happens beyond that. And so you're you're out like maybe just the first level. Like, I don't know, friendship. Yeah. You know, we'll, we'll like, we'll see if we, you know, connect again.

And then the next level up is like, okay, well, if we hook up, you know, then, then we're on to now another level I would imagine. I mean, I, this world is so, so far in the past for me, I'm imagining at least one other level before life partnership. We're together forever. But there are these levels to romantic relationships.

And so I'm curious if you see these same levels in friendships. I mean, yes, like we know like. Okay, that's an acquaintance and that's a really good friend. Do you see the same thing?

SS

Yeah, I think. But what's cool, yes, there are obviously different levels of friendship and also but but the best part about friendship is that they're so much more fluid. So it's really hard in romantic relationships to go back a level you can't. It's really hard to backpedal. Like really hard.

JW

Oh, I haven't thought about that. Yeah.

SS

Yes. So, so when you make a new friend or even with friendships that I've had my whole life, oh my God, there's such an ebb and flow to those friendships or even the friendships I've had for the last five years, nine years, two years, five months. It doesn't matter. It's like there's just this ebb and flow and both people can show up as much or as little as they want to or can, and that like like the parameters are. So there's just so much more elasticity to it.

JW

That's fascinating. So yeah, though that that yeah. So you can't go back in these romantic ways. And that's why when, when there's a divorced couple and we hear that they're still friends and that like everything's cool and they can still hang out, like that's mind blowing. Like what? Because. Yeah, and that's because of this assumption. Like, you just can't go back, love.

SS
Well, yeah. And that becomes really complicated too, because, you know, parents, single, you know, divorced couples who have to they have to co-parent. Usually you would hope that they are right and a very close warm amicable co parenting relationship is really like ideal for the kids. Right. And every everybody really. But then you have these people who are dating and meeting new partners and then the new partners are like, wait, they're like so close with their ex.

Like this feels threatening and so I, I just feel like, I think that as adults and as parents, I think it's just important not to put so much pressure on our, our husbands, wives, spouses, life partners to give us all of that, that friendship. Right? Like we can't get it all from one person. The rules are set for our life partnership.

Okay? Like you've hooked up a ton. You're married, you've got kids. There's like, all these. I mean, that's really has very little flexibility, to be honest, you know, and so I think that's why having friendships as an adult, as a parent outside of your home life partnership is so important. It really is.

JW

I just I just remember one of the really great quotes from the podcast that we released at the beginning of August with Blake, and she says that she thinks about friendships as living organisms. and I love that because like you really, you cultivate it, you nurture it. And, and, you know, like things change. There is this like developmental arc. But I would I have to think that romantic partnerships are also living organisms like they are. The other thing that they have all these rules and they're more structured.

And so I was thinking, okay, what's the difference between these living organisms? And I don't know, this just popped into my head. The romantic relationship is the living organism where you're like, this thing has to bear fruit, like, because this is what I, I'm going to need the fruit to survive. Like I'm going to need the fruit too.

Like, yes. So it's like, oh my God, like, I cannot mess this thing up. But then the other friendships can kind of come and go. It's like, you don't need a flower, you don't need to produce any fruit. Maybe sometimes you will and maybe sometimes you won't. But it's like.

SS

I love that. That's really great. Yes, I love that. That's true. I think it's like that our life partnership should be where we put the most kind of focus and energy on nurturing. Right. And the nice thing is that the more connections you have outside of that, the less kind of pressure there is right to like make everything at home feel perfect if you have if you're if you're getting your emotional needs met in multiple different ways.

Right, because one person can't do it all, you know. Right. Yeah. So, yes.

JW

Yeah. That's that's a that's a big thing. I in previous academic life, one of the things I love to study was this transition, like basically this transition from old world traditional communities to these modern societies that we now live in. And that if we, we can we we can actually trace the history of love and like like the history of paired partnerships and that they used to be part of these large social networks, you know.

And so we wouldn't expect all of our needs to be met by just one other person. But then the world comes along. And in these modern societies, like, Oh my God, now all everything I need in life is put on to this other person. So, right, I'm imagining now that this is probably a really big reason why friendship is so important. Like, is this the key for you?

SS

I think it is, honestly. And I, as a matchmaker, I mean, look, obviously, my clients hire me to find them a romantic partner. But oftentimes I watch these connections unfold as friendships and those have happened to me also. So I have a lot of friends that I made over the years that started as a first date.

JW

So do you have any friendships where things get really serious and then you were able to pull it back to friendship because that is what you mentioned before you like. It's really hard to go back.

SS

Okay. Those friendship. Yes, I'm still friends with men I actually dated, which my husband and I laugh about all the time. Like he'll meet someone and be like, Has he seen you naked?

Maybe, maybe not. I don't know. We're cool. Like, he has his own list and I have mine, so we're cool. Like, it's all good. Like, we're like we neither of us are bothered by it, but so yes, I happen to be, but I'll tell you, those friends are not they're not people I'm friends with, like talk to on a very regular basis, but they're still like, we're in each other's lives.

We hop in and out when it feels right. We're connected. I mean, look, Facebook, Instagram, it's just so easy to stay connected, very loose, like on such a surface level.

JW

Okay, so that's a good yeah. I think just because we, we earlier we mentioned how the online situation just being online social media everything has affected the dating scene. How do you think it's affected friendship?

SS

Oh, honestly, I think it's actually amazing for friendship. I, I love it. I encourage parents. So like I said, I'm so lucky that I have friends still that I talk to every day almost for like 39 years. That's very unusual. But I think that a lot of times, like I've had people reach out to me on Facebook or I've reached out to them just because I felt this like, Oh, I saw a post from like an old friend.

I'll just send her a message because that really touched me. Not a public message, like, not a comment, like a direct message. And then suddenly we like this, like we rekindle this little connection, and then sometimes that turns into something really seasonal but amazing. And so I think that a lot of times people are insecure about like, oh, I would love to reconnect with that person.

Like, do it. There you go. It's so easy. You're hiding behind a computer screen and you never know. Like, you might just reach out and, like, have this. This like a new spark happen again, right? With, like, an old friend and get on a face time and then end up planning a trip to see each other. If you don't live in the same place, or sometimes people will move from with another, like let's say you grew up with somebody and then they live somewhere further, like somewhere else.

And then you realize that they moved back. Hi, like go grab coffee or say hi. I think it's so hard for working parents and just all parents to create and, you know, create friendships and also meet new people. You can also go back to connections that you've had from so long ago. And I think Facebook is a really great way to do that or Instagram.

JW

Well, that's really yeah, the connections that we had so long ago and then reconnecting with those people. I've had this experience as well. It's like, Oh, we were like really good high school friends and then we lost track and then, oh, now we're connecting again and it's almost like this instant, like we can just pick back up. Yes, but making a new friendship at like I'm 45 years old, making a new friendship today.

Well, with you, Sophy, has been just a breeze. But beyond that, you know, it's like it's it's more challenging. And so what do you think makes it so different? Like, why is it so much easier to make friends when we're kids and and teenagers than it is to make friends as adults?

SS

Oh, God. Because kids are just so Zen like moment, like, in the moment, like, oh, cool. We're like playing the same, like, video game right now on our phones, like, whatever, right? Like, I watched I watched Audrey the other night. Sit down next to my friend Sydney's son, and suddenly, like they had never met before, they were playing war with cards.

We're like, Here's a deck of cards. They just went at it. Like, I was like, Oh God, this is so awesome. Like, it's so hard to even they're playing because they're playing and as adults we don't play that much anymore. We're just like, our brains are so like going.

JW

Okay, so that, okay, what, what just popped into my head as I'm thinking. Absolutely. I totally remember that being in elementary school and how much easier it would, how easy it was to make friends be like, we're just going to go out on the playground and play soccer together. Or, you know what? It's just, boom, we're all we're all together.

And there's this play. But then, of course, middle school comes along, things get often it's weird and hard and I remember that that that's how I felt. And then on into high school and you know, I connected with some friends. What I'm about to say, though, I want to say parents, if you're listening to this in the car and you don't want your children to hear anything about about ex, if you don't want them to hear things about high school that you would rather than not.

So one thing that I'm realizing is one of the reasons I really got into smoking cannabis. I call him cannabis now to be proper you. Yeah we I had ever in high school is that it was like an instant way to connect with other it totally it was like okay basically what toys and playing were when when I was a kid it was like, oh, you smoke weed I smoke weed.

We can hang. And then boom, the walls come back now and now we're connected and boom. My social network expanded so much because of like oh minded too.

SS

I mean, weed and alcohol were just wonderful for that. Like, yes, all the walls come down like all the like, you know, the anxiety, the social anxiety, the neuroses, like all that.

JW

Well, it does also have have. Yeah. So that stuff comes down. But it was always just like the simple act of just. Oh, yeah, just like, oh yeah, doing something together. And this, this is connected.

SS

Here. Hit this, hit this. Yeah. Hey. Yeah.

JW

Well, that's another thing. Yeah. So now as a as an adult, as a parent, I imagine if I developed a, like, regular cannabis habit, I might be able to expand my friendship again. But outside of that, I don't know. I don't know how.

SS

That's going to like, effect your productivity now.

JW

And I don't know exactly, but it does help me to reflect on maybe why it might be harder to make new friends as an adult. So, Sophie, how. Yeah. Can can can you, can you speak a little bit about this? How so? Well, let's just let's just start. Start here. How do you make new friends otherwise? What is your way?

Like, how do you do it for yourself? So.

SS

Okay, so I was thinking about it before we did this. Like the friends I've made as a parent, like new friends, right? That came after I had children. And it's really hard because our free time shrinks to basically nothing at first. I mean, it’s so precious. You just don't you're like, I don't want to spend any of my free time with anyone unless this is like the shit. Sorry. Like, it's just you can't even. It's like gold. It's like it's just you're so and I'm so picky about it. And and to be honest, this really does parallel with what I do for people for a living.

I mean, these people are like busy executive, single parents running their businesses. They're paying me for that time to like find people, meet them, sort through them, and then just give them like the nuggets like that are really good potentials, but you can't do that with friendship. So I encourage, like I found that like my best friends and really like to today I would say to date I have like probably one really, really close friend that I made after my kids were born.

Like, maybe more. But my friend Kim comes to mine and she was just here yesterday. Her twins and my twins went preschool together.

And so we would sit on the playground and talk and just. Just shoot the shit. Like, we would be like. Okay. And we became. Well, it didn't obviously help that Sasha and Audrey and Lillian, they were just like more like happiest together. But we really like, really liked each other. And she would ask me for dating advice because I'm a matchmaker.

And I was actually there at the day she told me about her first date with her husband that she just married two weeks ago. So that was seven years ago. So it was just and what I what I'm getting at is, if possible, when your children are young and you do supervised playdates, where it's a playground or it's someone's house, you don't just drop off a four year old at someone's house.

You're there with the other parent. That is like a really good time to screen them as a friend. Right? I call it screening and matchmaking. I'm going to screen this match for you, but it's just a little kind of forced together time. But it's limited. It's like a first date. You're like your kids are playing and you can chat and.


JW

It has this, well, I like to use the word like instrumental. So it's like, we're not really doing this because we're screening each other, right? Because we need to supervise our kids. And so super low stakes that it like like I have no obligation to reach back out to you. You have no obligation to reach back. Right. So it's like as low stakes.

SS

Absolutely. Exactly. So there's just no pressure and you could get to know and then and then like if things are jiving, you're like, okay, like this could be a front again. It all goes back to letting go of the outcome. Like, I'm like when you're not focused on the outcome of a human connection, I think it just allows things to just organically unfold however they're going to unfold.

And so and it's nice look, but not all of us have little kids anymore. So look, my my twins are nine now. I mean, the other day, I had a mom approach me at camp who was like, hey, our girls really like each other. Can I give you can I get your number? Like, I want to do a playdate with that? And I was like, whoa, this is moving like really fast. What's my number?

JW

Yeah, like, that's the equivalent of like, like kissing before we've even gotten ach other's names. Yeah.

SS

It was really like, whoa. I was like, this is like we just jumped to second base right away, but yeah. Slow your roll. Exactly. And it does get awkward also, I think like sometimes when our kids make friends and then you're like with the other parents or you're at a birthday party or whatever, and then like other parent, another parent is like, Oh, we should get a, we should do a double date, you know, and I'm in my head thinking.

JW

There is no way this woman do that. Okay. So I've, I've two things. First, I'm like if I think of people on a spectrum, yeah, a whole continuum of like people are just naturally super social and boom, boom, they're out there. And then people who are more introverted and quiet and to themselves. So if I think you are on the far end of the more social spectrum, like you are like I am, you're you're out there, you're connecting, you are an actor.

That's why you're such a good executive matchmaker. But I want to like slow down just a little bit and recognize that for a lot of people who are going to be on the other end, who are going to be more introverted, are going to be much more maybe in their heads about that interaction of, yeah, how do I approach another parent?

How do I know? Like they might be the the parent who, who goes too fast because they're like, I don't know how to like, you know, how do I approach that? Like, I think I might be friends with this person or I could be I could see myself becoming friends with this person. So I'm going to ask and see if they want to go on a play date with our kids.

What advice do you have for that parent who is more introverted and is like looking for ways to connect and is afraid of moving too fast?

SS

Don't move too fast. Just think of like a really like ask them on a first date. So, so first parent, mom, dad date. I don't know. To me that is like, like, first of all, if your kids are young enough to do the play date, that's a perfect go to like, let's do a play date. That's a no brainer.

Again, that goes back to like, we're just doing this for our kids and then you can see how that goes. So but for those of us who have older kids, like I dropped Sasha off on that playdate, I wasn't there. I mean, I was just like, good luck. You seem cool. Yeah.

I was really kind of rolling dice there. But but no, but like for people who have older kids, like, you know, nine, ten, 11, whatever, and they're there, but they're like noticing that there is another parent that through the school or wherever or through activities that the kids do. I mean, you can do a couple of different things.

So first of all, you could do something really low pressure like, Hey, we should grab coffee sometime or Hey, after drop off, do you want to like grab coffee or something? A little lower stakes than we should get a glass of wine or we should go out in the evening evenings to have more pressure in general. And by the way, as a matchmaker, I actually highly discourage coffee dates because they're so horrifically unsexy and unromantic.

And so they feel more like a very platonic or even interview. So I'm just like, those are perfect for like and again, you have to think about whether that parent works. Maybe they drop their kid off and go right to work, whereas others don't or have more flexible. I've had people approach me and be like because they know that I go for walks after drop off some time.

Like if you both if like just find something that, you know, maybe the two of you have in common, right? Like if you're both people who probably work out like, hey, do you want to go for a like drop after we drop off our kids or whatever? Like go for a quick walk or a hike or like I said, just really low pressure. Coffee is just so easy. It's just.

JW

Real. Yeah, I'm going to do all this because I. This is just sticking in. My brain went to be good. Okay. Sorry for the romantic matchmaking sphere for a new so people that you're connecting for the first time if they do go out on that coffee date because it's so unsexy and so and romantic that then if there's a connection in that context, then boom, you've you've hit gold.

It's kind of like a way to really see, like, okay, the, like, take, take away all the other stuff is, is there a connection?

SS

You're challenging me. Because I really hate coffee dates for four dates. I guess you're right. Like, I'm actually being like, I'm contradicting myself because I'm telling you, let go of the outcome. Go in. Like you're meeting a new person, a friend, but also coffee dates are really not sexy and romance. They don't just don't lend themselves like there's just and honestly, I'm not I'm not like hard core. Like there are certain people who I match who I actually think do need to go on more of a coffee smoothie non standard date but remember these people are paying me a lot to achieve the romantic outcome.

JW

And so throwing them into just a Starbucks and a like egg like. Right, that's not Starbucks. Broad daylight.

SS

Caffeine. You're drinking caffeine. And you're just like, it's so nerve wracking to go on a first date. A coffee can really like, really exacerbate nerves. People interview for jobs at a coffeehouse like.

JW

All that, all that. And yeah. So I am affirming you or your choice there, but just that thought came up as like if in all these barriers a connection is made, then you know, yes, the goal like I have yet.

SS

I mean I have yet to see to have matched a couple successfully where their first date was a coffee date. So and I've sent out over 1500.

JW

Yeah, yeah. Right, right. It's A lot. You, you have some experience there. Yes.

SS

Yeah. So I don't know. It's just but but for friendship and for parents, it's awesome. And it's just I love it. Like, I love that idea and it's just like super low pressure. The other thing that kind of comes up for me though, is when another parent approaches me, right? Or maybe you're more introverted parent, right? And a person and some crazy extrovert like me comes over and is like, Oh, we should like, let's go for a hike or whatever.

And you're like, Wait, I don't know. It feels it could be like really uncomfortable in that moment because it's really hard for people, even extroverted people like me, to be honest in the it's really hard to like reject someone, right? Or like, God, it's so hard, so hard. So I thought about this and like I give this type of advice to all my clients who go on dates and at the end there's the so like, we should do this again.

I had a really good time and like, how do you respond if you're not sure, right? Or whatever. So I would say, like, if you're that kind of a little bit more like introverted person and you're being approached by a very outgoing person like me, I think like a really nice way to respond is to give yourself a, like, more time, right?

Like, Oh yeah, that could be fun. Let's text and see what, like what we can arrange over the next few weeks. Few weeks. That's like plenty of time. There's no, like, pressure. Not like this week or tomorrow. And then you can go home and think about it and decide and then like move slow. So I just kind of wanted to put that out there.

Yeah, because it's really hard sometimes for people and even for me sometimes, you know, to be like, No, that doesn't actually sound like something I want to do right now. Like, I'm too busy a new person. I don't know you well enough, you know? So, yeah. So that, that also kind of popped in my head as I was thinking about parent dating and friend friendship dating in the parenting world.

JW

I want to also talk about breaking up. And so I don't know. Now you're not I imagine you don't have really you're not there for the romantic breakup. You're there to put people together.

SS

No, I'm there for you. I'm there for both. Oh, no, no, no, no, no, no. I'm there for some a lot. Oh, yeah. Because I mean, I imagine a lot of people who will date and then they'll date for two or three months and then realize, all right, like, okay.

JW

Okay, there's a lot.

There are sometimes friendships where it's time to break up. I mean, if it happens. So, yeah, how can you help us think about letting go of a friendship when that time has come?

SS

Well, first of all, it's like deciding right for yourself. Like, is this friendship serving me anymore? Like what? What is. What's what's going on here? I found this happened to me in my life multiple times. Where I a couple times where even somebody that I knew from when I was in college, you know, and we had been like best friends.

So actually it happened with my roommate, one of my roommates in college. We lived together for four years in our lives. Just took these like really different paths. And she moved to San Diego at some point and just was like suddenly integrated with my friend group. Or I was obviously like, Oh my God, you're in San Diego. Like, Let's hang out and it didn't work well.

Like it was just like really uncomfortable for her. For me, she felt a lot of like it was just it just wasn't a fit at the time. We were in like really different places in life and eventually it hit like a breakup. And I think we were just like, like at that point, this is like with a history with someone, right?

Like we had to like have an honest conversation about it and it was more just like, listen, like this is not working like ever. Like, I don't feel good when we interact, when we talk. But I don't think that most friendship break ups happen that way. That was like a very honest, raw, long term one. I think sometimes honestly, things just fizzle.

Like, Have you ever had that happen?

JW

Well, that's that ebb and flow. And right where there's just an ebb and it never flows again.

SS

Exactly. And I think I think you need to just think about what a friendship, how that friend makes you feel like. How do you feel when they when you even get a text from them? And I actually just it's funny enough, I just had a conversation I think yesterday or the day before with a girlfriend of mine. I think I even told you about it, Justin, who went on to tell me, Oh, I'm having I'm going to an IFS lecture tonight like we had actually not, we've known each other since we were very little.

She's part of that crew, the Jew crew and we had really like drifted apart. And that was conscious on her part for the last few years. And yesterday or the day before we talked and she told me, I've just pulled back from you because I felt judged. I felt like you were always trying to fix my single hood.

My I mean, it was really and I actually knew it deep down inside. I knew it couldn't help myself with her before and then. Now it just it was pretty rad because we had this, like, amazing conversation. And I almost feel like we just got back together.

So I think you just need to decide. And that's what she did. She decided it for herself. I was reaching out to her all the time and she was like, Aha, aha. Like she was blowing me off as a friend and I didn't push because I kind of knew I'm like, This isn't she's not down for this right now.

And I think we just all need to be aware of like a, how we feel in a friendship and when it's time to sort of back off or let them back off, you back off, whatever it is, right? Yeah. So that's kind of my.

JW

Thought on that mean last friendship question and never will go into our our final three. Mm hmm. Well, I want to just briefly talk about being a parent and being friends with other parents. That makes sense. But being a parent and being friends with non-parents there feels to me like there's a gap there. Like I can think about my non parent friends and we're like we're friends.

But it's like there's something, we're like, you don't really get my life because being a parent is so radically different way. It just changes everything. So I'm curious, first off, do you have any non parent friends who are like super, super good friends? Yeah, I do. Oh I was. I did.

SS

Again, it's going to parallel a parallels to dating also and I'm I'm doing this because I'm so matchmaker Sophie talking here this is such a catch 22 in dating because single parents are like, oh my God, I like, I want to meet somebody who gets it, who gets the, like, all consuming existence of being a parent. It's just all consuming.

And you're like, Oh, I just want somebody. And then but then the problem is, and I think this problem comes in also with adult with with parent friends, right. If you were at the mercy of our children's schedules, activities, illnesses, medical emergency, medical conditions, I mean, yeah.

Just throw those some big medical conditions in the mix. I mean, suddenly you're like, when can and then the other parent has their things. And that happens with dating too. It's like, sure, we get each other and when we're together and connecting there is so that understanding. And so there's this like bond and understanding and connection that happens between two parents, both in dating and friendship, but logistics.

It becomes really logistical sometimes, and it's almost difficult to make time or for them to make time and you guys to have the right times line up, to spend time together, talk to each other, even on the phone right. Okay.

JW

So I just realized that I that I have this because I do have several really good non parent friends like just dear, dear, non-parent friends and just realize I carry this silent suppressed judgment any time that we're trying to connect and their schedule is somehow blocked off. And I'm just like, what are you doing? Like you have kids, you do not I I'm sorry.

Whatever is how I do that. Your life I guess that's juggling like I do that you should be able to fit into my schedule right.

SS

And that's we have to be careful as parents not to do that. I do the same thing. So I have to I would say to really close friends both from college who are like two of my best friends. I know I say that about a lot of people just end, but they are there's like a very. Yes, trust me, if you ask them, they're going to say the same thing.

So but they're both from college and they're both unmarried with no kids. And there's just something so great about connecting them. And suddenly I'm not just talking about my kids the whole time. Suddenly I am Sophie. Pre-mom Sophie and it's awesome. It's amazing to be able to just reconnect with like who we are, the parts of us that aren't a parent, like we're not, you know what I mean? Like who we were before we were parents and just it when I am with my friends, we talk to the ones that are married with kids. Like we talk about our kids and our husbands and our wives and our everything.

Like, it's just like those conversations just keep happening. It does. It's, like, impossible to get away from them. But it's so fun to sit down with somebody who isn't all consumed by that. And then suddenly you're like, Oh my God, there's this whole other part of me that I miss. Yeah. So I think it's important and nice and I really, I really enjoy that. But I do the same thing, by the way. I'm like, What? You're busy. Like, what in God's name could you be doing right now?

JW

It's like, I love, Oh, all right. So at the end of every podcast, we ask our guests these three questions, so we just roll. Rotherham Just and I love how we can compare how each each guest answers these. So the first one is Sophie, if you could put a giant Post-it note on every parent's fridge tomorrow morning, they wake up, boom, the post-it note is there. What does it say?

SS

Okay, this is going to sound like kind of generic, but it's just it's what I came up with. You can do hard things.

JW

Right? You're tired, you're exhausted. Your kids lunches need to be made. Everybody. The lunch closed and out the door. You can do it. And then after running that gantlet, then you have to go to work and you can do it. Yeah. So Sophie, is there a quote recently that has changed the way you think or feel?

SS

Okay, so I thought about that. I mean, this didn't change the way I think or feel, but it definitely ever since I saw this quote, it like fully embodied my experience as a parent and as like a human in general. It's the real quote. Let everything happen to you, beauty and terror. Just keep going. No feeling is final.

JW

And then finally, what is your favorite thing about kids lately?

SS

I've found that my favorite thing is I love explaining to kids these cons that's in life that are so mundane to us as 45 year old grown ass adults like something as simple as like, I don't know, just like medical insurance. Like they look at a bill and they're like, What is this? And I'm like, Oh, this piece of mail. Here's what's on it. Like, here's how this works.

Here's the medical bill, or here's even like a power bill, whatever. Just like that sense of like the ability that if you kind of just really get into the moment with kids like be present, you can kind of relive that, like, sense of wonder, terror and newness that we just you lose as you get older and live more years, you know?

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Podcast Ep. 47: Bridget Cross, LCSW, Leads the Yes Collective Therapist's Circle

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The Yes Collective Podcast

Podcast Ep. 46: Anne & Justin's In-between-isode on the Working Mothers (Erin Erenberg) Interview

Podcast

Podcast Ep. 46: Anne & Justin's In-between-isode on the Working Mothers (Erin Erenberg) Interview

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Yes Collective Podcast

Podcast Ep. 56: Waking Up to Trauma and Healing as a Parent, Partner, and Person, with Tanner Wallace, PhD

Podcasts

Podcast Ep. 56: Waking Up to Trauma and Healing as a Parent, Partner, and Person, with Tanner Wallace, PhD

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Yes Collective Podcast

Podcast Ep. 55: Recovering from trauma with therapist and trauma-sensitive yoga facilitator Ruthie Duran Deffley, LCSW

Podcasts

Podcast Ep. 55: Recovering from trauma with therapist and trauma-sensitive yoga facilitator Ruthie Duran Deffley, LCSW

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Yes Collective Podcast

Podcast Ep. 53: How to find and nurture deep friendships with executive matchmaker, Sophy Singer

Podcasts

Podcast Ep. 53: How to find and nurture deep friendships with executive matchmaker, Sophy Singer

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The Yes Collective Podcast

Podcast Ep. 52: Friendship & Emotional Health with Blake Blankenbecler, LPC and Jenny Walters, LMFT

Podcasts

Podcast Ep. 52: Friendship & Emotional Health with Blake Blankenbecler, LPC and Jenny Walters, LMFT

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The Yes Collective

Podcast Ep. 51 - "Best of Yes" with Sleep Scientist, Kate Simon, PhD

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Podcast Ep. 51 - "Best of Yes" with Sleep Scientist, Kate Simon, PhD

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The Yes Collective Podcast

Podcast Ep. 50 - Healing heart & mind through the body with somatic psychotherapist Betsy Powers

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Podcast Ep. 50 - Healing heart & mind through the body with somatic psychotherapist Betsy Powers

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Yes Collective

Podcast Ep. 49: Wellness Reset Meditation: The Power of Three Deep Breaths

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Podcast Ep. 49: Wellness Reset Meditation: The Power of Three Deep Breaths

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Yes Collective Podcast

Podcast Ep. 48: The June Mom-isode with Audra & Anne

Podcasts

Podcast Ep. 48: The June Mom-isode with Audra & Anne

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The Yes Collective Podcast

Podcast Ep. 47: Bridget Cross, LCSW, Leads the Yes Collective Therapist's Circle

Podcasts

Podcast Ep. 47: Bridget Cross, LCSW, Leads the Yes Collective Therapist's Circle

By

The Yes Collective Podcast

Podcast Ep. 46: Anne & Justin's In-between-isode on the Working Mothers (Erin Erenberg) Interview

Podcasts

Podcast Ep. 46: Anne & Justin's In-between-isode on the Working Mothers (Erin Erenberg) Interview

By

Yes Collective Podcast

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