233. Lessons From 104 Dates with Heidi Friedman

In this heart-to-heart conversation, I sat down with Heidi Freeman, successful attorney and author of "Love Lessons: 104 Dates and the Stories That Led Me to True Love." Heidi shares how turning 40 sparked her quest to understand what true love looks like by interviewing couples in strong relationships. What began as research turned into 11 core themes about authentic connection. With refreshing honesty, Heidi opens up about her 104-date journey, complete with hilarious mishaps, surprising insights, and the beautiful moment when she finally met her husband Will.

This episode cuts through the anxiety about modern dating to remind us that love requires resilience - and is worth 100 disappointing dates.

Key Moments

• Turning 40: Heidi realized she didn't know what true love looked like or felt like and decided to interview couples in solid partnerships
• Research: Heidi interviewed 50+ couples separately to find themes
• Mutual reciprocity: The most impactful insight was how partners take turns supporting each other through life's waves
• The myth of love at first sight: No one Heidi interviewed mentioned this - instead they talked about initial connection and safety
• D04 dates: Heidi shares both hilarious dating disasters and meaningful lessons learned
• Finding Will: How she met her husband through yoga connections and recognized the difference in how she felt
• Dating in the wild vs. apps: The benefits of meeting people through activities vs. online

Quotes

"I had to put on my big girl underwear and go back out there." - Heidi on persevering after dating disappointments

"I think it's not us. This is the way we are socialized...to value relationships, which is awesome. But then we're also socialized to put our own personal value in relationships, and that's what's harmful." - Sade Curry

"Mutual reciprocity and safety... even if you didn't have all the other sprinkles in a relationship, but you had these, you could make a good relationship out of that." - Sade Curry

"What if the next date is him? I would constantly say that to myself when I didn't want to go." - Heidi on staying hopeful

About Heidi:

Heidi Freeman (formerly Goldstein, born Eisman) is a successful attorney and partner at a large law firm specializing in environmental law and social and environmental governance-based counseling. She's written her first book, "Love Lessons," chronicling her dating journey and the relationship insights she gained. Heidi has previously written for Bloomberg Law, 360, and other professional publications. She lives in Cleveland Heights, Ohio with her husband Will and their blended family - two children of her own and two bonus children with Will.

Connect With Heidi

• https://heidifriedman.com
• http://www.instagram.com/lovelessons104
• Podcast: "I Love You More" with her 22-year-old son Zach (available on Spotify and Apple Podcasts)
• Book: "Love Lessons: 104 Dates and the Stories That Led Me to True Love" (Available on Amazon, Barnes & Noble, and Goodreads)

Ready to Transform Your Dating Life?

If this episode resonated with you, I'd love to help you apply these insights to your own dating journey. Book a complimentary dating consultation call with me at sadecurry.com/info and discover how you can build the confidence, clarity, and connection skills to find your perfect match.

Transcript

Episode 233: Finding Love After 104 Dates with Heidi Friedman

SUMMARY KEYWORDS

Heidi Freeman, Love Lessons, dating journey, mutual reciprocity, relationship themes, initial connection, personal growth, dating apps, authenticity, relationship advice, social media, personal development, dating strategies, love stories, podcast.

SPEAKERS

Sade Curry, Heidi Friedman (Heidi Freeman)

Sade Curry [00:01]
Hello everyone. Welcome back to the podcast. I am your host, Sade Curry, and I am so excited today to bring you my latest guest, Heidi Freeman. I'm gonna read her bio, because Heidi is not a dating coach, you are just a real human who has written her story and wants to tell people. So I'm really intrigued, and I'm just gonna read your bio. Heidi is formerly Goldstein, born Eisman. You're a successful attorney and partner at a large law firm specializing in all areas of environmental law, social and environmental governance based counseling. But you've written a book called Love Lessons.

[00:54]
It's your first book, and

Sade Curry [00:57]
that's what we're here to talk about today. But also you've written regularly for Bloomberg Law, 360 and other publications related to your professional life and your experience as an attorney. You live in Cleveland Heights, Ohio, with your husband Will and your fur baby and your blended family, two children of your own and two bonus children with your partner. So welcome Heidi to the show. It's such a

Heidi Friedman [01:23]
pleasure having me. I'm so excited to chat with you absolutely

Sade Curry [01:27]
so I really want to just dive in into the book, because I love I come from an IT background. So I love data, I love research. And you set out on this journey to figure love out.

Heidi Friedman [01:42]
I did. Tell me about that. What happened there? So I turned 40, which was 15 years ago, and I will say it's a little embarrassing to admit, but I decided, as I was turning 40, and that was kind of this pivotal point for me, for whatever reason I think people have when they reach those decade markers, you know, whether it's 40 or 50 or 30, you sort of contemplate your life, and I decided that I did not know what true love looked like or felt like. I decided I had never been truly in love. And yes, I had been married, and I did love my ex husband, but not in that way that I was looking for.

And so I went around, and I decided that I was going to interview friends and people that I knew fairly well, that based on my own observation, I felt that they were in a very strong, solid, good partnership. And I wanted to ask them why they knew it was that person. How did they know? It was very elusive to me. It just seemed this gray area when I'm a super black and white. I was looking for an answer, and I was all about data, and I was flying around doing depositions, because I had a very national practice. Spent too much time on airplanes back in those days, and I would read over the notes from my research, and I realized that there was themes, and no matter how many people I talked to, the same themes presented themselves over and over again.

And so I ended up writing the themes and chapters of a book that I then parked for a while, because I did get to the point where I started not to hear new, even each story is a little new, a little different, tweaked a bit. It was really the same theme. So I felt that I had done the research and I had put in the back of my head, and then I moved forward.

Sade Curry [03:34]
Were there themes that were surprising to you that was like, oh my goodness, I had no idea this was a part of a good partnership?

Heidi Friedman [03:43]
I would say that they were less surprising than they were impactful or insightful. Meaning, I think the me that knew what a good relationship looked like had these ideas, even though I had never felt them. Probably the most impactful one, and I wouldn't say it was surprising, but it was really how folks talked about taking turns taking care of each other. I am a serial fixer, and sort of always jumping in and things like that. And these couples and I never interviewed them together, I always like to talk to people separately, but even separately, they would always talk about "this happened, and she pulled me up, and this happened, and I pulled my partner up," and so it was a lot of sharing back and forth.

And it was at a time when I was doing a lot of therapy. I'm a huge fan, and my therapist and I had already come up with this weird visual about life being a series of waves, and basically you're going to go under at some point and you need someone to pull you up, and you can't be the puller upper every single time, or it's going to be exhausting. And so I had already had that visual in my mind, and then it came to life through these interviews. So that was the one that was the most impactful to me.

The only thing I would say that was surprising is that I talked to 50 some people the first time, and maybe six more when I was writing the rest of the book post COVID. I wanted to make sure the theme still stuck and they were still true. No one talked about love at first sight. People talked about an initial connection. "I knew I had. It felt different. I felt like I could share myself. I felt safe." But no one used the word like "I saw her across the room. It was love at first sight," or "I saw him," whatever. And so that was probably the only thing that was surprising to me. And maybe that's just a little bit of a fantasy, that idea.

Sade Curry [05:47]
I think it is. Not that it can't happen, but that the way we center it in love stories, in the media, in our young teenage fantasy crushes, I think, is harmful, because there can be interest at first sight. There can be something interesting or something that catches your eye, right? It could be the way the person is talking, or the way they are dressed, or even how hot they are, like all of that is legitimate. Is legitimate interest at first sight. 100% of love at first sight, I think, is not as useful as we've tried to make it.

Heidi Friedman [06:29]
I think I'm not even sure that's possible. I think it's attraction at first sight is kind of where you're going and what I believe. There definitely needs to be a physical attraction component. You can't make yourself like somebody, and I talk about that a lot, but it's different to be physically attracted to someone than to actually feel true love, which I think actually develops over time, and you know it when you feel it, which was amazing to me, because it was this aloof thing, and then when it happened to me, I had no doubt in my mind.

So it really is about listening to your gut but also tuning it up. I mean, I had gone through 10 years Sade of like, so many dates and like self discovery. It sounds super cheesy, but it was like I did not have confidence in my personal life. In my professional life, I was a badass already. I mean, I knew what I was doing. I felt good about my professional career, but personally, for some reason, I didn't feel worthy. And it took 10 years and 104 dates and lots of other things to happen for me to really feel worthy of the partner I finally was able to get.

Sade Curry [07:41]
I mean that story, I've just heard that so many times over and over all my coaching sessions, women I've interviewed on the podcast, and it's not, I think it's not us. This is the way we are socialized, right? We're socialized to value relationships, which is awesome. It's not a problem. But then we're also then socialized to put our own personal value in relationships, and that's what's harmful. So it's sort of like this fairy tale that you have to have to have accomplished, in one of my clients words, to have accomplished adulthood, you have to have achieved this. And it's quote, unquote, so hard that it's hard to feel confident when your entire existence as a human is hinging on.

Heidi Friedman [08:27]
Well, I mean, I heard something yesterday on a podcast with a friend, and she came up with the term Noah's Ark syndrome, which I just caught on to that, which is sort of this syndrome of feeling like you have to be paired up, right? You have to have an other. And there's lots of reasons people don't. I know there's sort of single by choice. What is that? SBC, these people use that terminology. I'm not cool enough to know all of those, but there's also people that do want to be paired up, but are smart enough to wait.

I mean, I wrote the book, in all honesty, even though I did the research initially, I actually wrote the book 12, 13, 14 years later for my four kids, because I really did not want them to make the same mistakes that I made, or that Will might have made, in terms of like not settling for what we really wanted in life, and in trying to make sure you found the best partner for yourself. And I think that it's accomplished its purpose. I believe for the most part, they all took it in, and we have a lot of good relationship discussions now. And my son and I started a podcast, which we can talk about later, but that was the real purpose for me to write it.

So the fact that, I mean, if I can help one more person have hope and find love, I would be thrilled. I love fixing people up, because I got fixed up, so I want to pay it forward. And I just think the world needs more love and hope now. I mean, and that is not a bad thing, and so the more we can spread it for ourselves. You know, with connections, whether they're friendships or professional or romantic. Yeah, 100%.

Sade Curry [10:21]
And you know, you had said that one of the most impactful things that you discovered was what I've referred to, and I think generally is referred to as mutual reciprocity, in that where one partner pulls the other person up when they need it, and then the other partner does their turn. And it's like this. You know, both petals are peddling depending on what part of the cycle that you're in. And I think that's also something that is missing in many ways in society. That's how the human race has survived, right?

I was reading this story about, they found these 1000 year old bones of a woman or something, and her femur was broken. So this was an elderly person, and the thigh bone was broken, and where they found it, and the other fact that they found it with the village and on the trail showed that humans have been caring for the most vulnerable for 1000s of years. That's how we have survived as a species, is caring for people who can't care for themselves. And that's just exactly what came to my mind.

I was like, yeah, at different points in time in a relationship, if it's gonna last a long time, you're gonna go through all kinds of things, and it's important for each partner to do their part. And often, when we find that relationships don't work, it's because that's missing.

Heidi Friedman [11:58]
Right, where someone's trying to fix somebody or change somebody. I have a whole chapter on no project dating type of situations. I have plenty of those as well. So that's just disappointment and frustration, frankly. So I made that mistake way too many times and it's really part of valuing yourself is finding someone who doesn't require that, that you guys can grow together, rather than feeling like you have an obligation to make them different or better or quit something or whatever.

Sade Curry [12:40]
One of the principles I teach my clients is that there are certain you don't do married things when you're dating, like, so the mutual reciprocity, where you're pouring into someone's career, that's for later, right? That's not for the third date, which I have a client who went on a first date, and this man spent the entire day talking about how he lost his job.

Heidi Friedman [13:06]
Right? And she's your therapist? But you know, so I'd say to my kids, it's something I've always said, which is, like we all try to be our best selves, right? And I truly believe that you need to be your best self before you're ready to have a relationship with anyone else. And most of us have a lot of work to do. And I certainly did mine, and I was talking to my son today, actually, about the fact that when you're 22 like he is, for example, you're not even emotionally involved. And so people that get in these long term relationships in high school or college. It amazes me, and they are the exception to the rule.

And I've decided my parents, for example, have been together since high school, and they are most definitely each other's person, and gave me this idealistic, almost marriage situation that I didn't necessarily ever understand, to be honest with you, because they've been together for 60 some years now. And they just probably, I think, knew what each other wanted at an earlier age. And I think most people do, it was also a different day and age back then, which things are a little bit different now.

Sade Curry [14:20]
I've looked at some of those couples as well, and what you'll find, because there were a lot of marriages in that day and time that didn't work either. So there are social psychologists have done studies on what creates longevity in long term relationships, and some people just happen to without trying fall into that either, because they saw those relationships. So by osmosis, in their own families and in their own environment, they picked up on those cues. And so they just kind of do things because it's part of the environment.

There are those people and God bless them, they're so blessed to just have that. It's like when you're born into a family of hunters, you just kind of know how to pass the deer. Nobody has to teach you that kind of her hair, right? And so some people do have that. But there are actually things like, I think similarity is one of them. So similarity of values is highly important. Similarity of lifestyle, the opposites attract cliche is not true at all.

Heidi Friedman [15:31]
That one's super interesting. Today, I feel like I saw as many opposites that did attract, that didn't attract, and I didn't find that to be very significant to me, because I did. There was plenty of places where people were sort of opposite and they played off each other. And then there's, like, my situation where my kids, our kids, make fun of us, and my husband and I have our same like, literally have the same brain. So, you know, I think it just depends.

Sade Curry [16:06]
Fit. Yeah, it's not because they're opposites or not opposites. It's the other thing. So you could be opposites, but if your lifestyle is similar and your values are similar, and you're in the right place in life at the same time, that kind of works out. And then if you are similar, and all those other things are in place. So I mean, they talk about proximity, they have a list of things. Esthetics is part of it. So we tend to look for someone who has sort of like, not necessarily similar features to our caregivers, but like similar micro expressions.

All of those little things play into that, but I do love that you brought up mutual reciprocity, because that is, I think, even if you didn't have all the other sprinkles in a relationship, but you had mutual reciprocity and safety, you could make a good relationship out of that.

Heidi Friedman [17:02]
Sure, safety is an interesting one, and so the one thing I'll say about safety is, while it showed up in the initial interviews, not using the term safe the initial interviews, it was much more "I felt like I was at home. I felt comfortable. He embraced my crazy," like those were the kinds of words that I had written down.

I did six interviews last year just because I said it's post COVID - what if relationships are different and it's not the same? And so I interviewed different people, and I heard the same themes all over again, but the new theme that emerged so clearly was "I feel safe," and I personally wonder if that relates to what happened during COVID, which made people realize that the significant other they had in their life brought them safety during this very unsafe time. And all six people I talked to talked about the element of safety and how important it was as a foundational piece to the relationship. So I do feel that that's a post 2020 not that it's different. It's sort of enhanced what I heard before.

Sade Curry [18:16]
Amazing. Now, did you write the book while you were going on the 104 days after, like, where was this happening?

Heidi Friedman [18:24]
So I wrote the first book, part of the book, in my 40s, and I had kept a journal through most of the process in the book, there's like little journal entries throughout the book. Those were the hardest, by the way, we can certainly talk about that, but that I hate thinking back how lonely and unhappy I was, but anyways, and then I wrote, it had interspersed a little bit about my dating in it, but then I found it several years ago on my computer, which seems crazy after you write a first part of a book, you forgot about it, but I did, life happened, and I was stopped.

And I was like, I would love to apply this to Will in our relationship, and I wonder what it would look like. And I reread it, and I decided all the themes applied, including the new ones, and I had a few of my own. And then I just started going through and talking about some of my dates, interspersed with the themes and Will. And then at the end, you have 11 love lessons that I learned through the journey of my research, my relationship, my dates, all of those things.

And so I did have a bunch of notes in my journals about my dates, and frankly, the ones that I wrote about I would never forget about because there was some really bad, awful dates, and I will say, like, also some of the funniest experiences of my natural life, and really good cocktail banter when you had to show up as a single without a significant other for some kind of wedding or garments for something, I had great cocktail conversation about my dates.

Sade Curry [20:02]
Did you know you would end up going on over 100 dates before finding your person?

Heidi Friedman [20:09]
I would have never, ever thought that I would have. Now wasn't 104 guys, it was about 55 people. There was three or four people that I dated for some period of time. So I met, went on multiple dates, and I did count those, and none of them were really relationships. My son taught me the term situationship, and I think they were more situationships, to be honest with you.

But no, I mean, I started counting after the fourth date, and I was being fixed up 10 ways to Tuesday, and I was like, okay, this is going to be a journey, and I'm going to just start counting. But I would have never, and there was many times that I was like, done. In fact, I think pretty close to right before I met Will, I was like, I'm done.

I had to go to a wedding by myself, and it was just the worst experience after I was dating somebody and had RSVFed for two and then she said, "well, it's too late to change. You're just gonna have to sit next to an empty seat." Now, is that not symbolic of my life at the time? But then that was literally the low that led me to the high of the fix up of Will. So you just gotta keep on keeping on. It's a journey. And if I was still laying in bed crying about that wedding, my life would be so much different. And so you just gotta, as I like to tell my kids, put on your big girl underwear and go back out there.

Sade Curry [21:33]
Yeah, if you want it. Because of podcasts and social media relationships seem like they're really fraught right now, like, oh my god, it's really hard to find a person. And it's never used to be this way. It's always been this way. I think.

Heidi Friedman [21:52]
It's always been this way. I think it's more publicized, and I think there's more experts on it. The one thing I think that's an interesting shift is, talking to girlfriends that are single and other people, people are very interested again, in dating in the wild, getting back into it, versus the kids who are in their 20s who are so tied to technology and the apps and all of that.

And so I think the people that are trying to find two life partners when you're in your 30s and 40s, there's this reinvigoration into dating in the wild and having in person events and meeting people and making connections, which I love, because I think an authentic meeting is always going to be better than trying to portray something on an app that is very hard to be your authentic self through that device.

Sade Curry [22:44]
It's interesting that you say that. My experience has been, people say a lot of things and do things actually quite differently from what they say. So 100% everyone wants to meet their partner in the wild. However, it takes a lot more effort. Yes, and so I will encounter people who are talking very vigorously about meeting people in the wild, but spending more time on the apps.

Yeah, so when I'm coaching women, one of the things we - our coaching model starts with the circumstance. So what are the facts? Okay? And when I, whenever we explore the facts of what's happening, it's interesting that the facts are that more a lot of people are on the apps now. They don't like the apps.

I think that's true. On that Friday night, right? They don't have any invitations, and nothing's happening. There's just all it's just one click away. And so what I what if I try to evangelize, is more of a balanced approach, because it can be a perfectionist fantasy to believe that you're going to go out in the depending on people's circumstances, children, career, travel, energy, I try to say, hey, why don't we just do all the things? Okay, so then that way we have what I call all the portals are open, and if he wants to step through one of the...

Heidi Friedman [24:13]
Portals, I like that. That's a good way to say it.

Sade Curry [24:17]
He's coming through. And you sort of have this sustainable energy where you are. You have your social calendar, whatever social calendar you can sustain versus "I gotta go out three times a week, even though I'm very busy." So you've got that. And then you've got the apps. And then you're talking to your friends and having them fix you up. And then you're talking about your dating journey on social media. So people who are in your network online, just keep it all open. I think that kind of takes off the pressure.

Heidi Friedman [24:47]
I totally agree, the one thing I would add, though, Sade, I think, is instead of just telling your friends, this is my big speech that I always give. So it's probably getting a little bit old for some people now, but you have to explore Intel people outside of your network. And if you just tell your current network, it's going to be the same people all the time.

And so I can't even tell you how many times I have counseled somebody to do this, so I'll quickly tell you the story about how I met my husband. So I am a huge yogi. I love hot yoga. I go to Cleveland yoga here, my friend Tammy Schneider owns it, and it is just my favorite place in the world. I've been going for decades. So I would go, and I would go on the weekends, and it was my break, and I would go in the front row because type A personality, I need to be staring at a wall in order to be like Zen during yoga.

But I would constantly end up doing yoga next to the same couple of people, and we would say hi and whatever, and then we'd talk a little. And eventually this one woman, Anne, said to me, "so what's your story? Like? Are you married?" And then we ended up really talking, and I would come in and share my bad dates with these - it was two guys and me and Anne. So the four of us, we call us the front row crew, and we really developed a friendship.

But after this whole wedding fiasco thing that happened to me, I came in the next day, and Anne was just beside herself. She wanted me to take her husband to the wedding, because no one should have to do that. And she told me that every time she sees this guy who she did not know that well, she thinks of me, and she wondered if I'll be open to getting fixed up with him.

And so at the time, by the way, I had absolved all my rules. He was 10 years older than me. I had this stupid rule that I wasn't dating anybody who was more than five years older than me. I hate rules. There should be no rules. And so I said, sure, by that time. And there we went. Now, there's more to it because he hadn't gone on a date in 24 years. He thought you still had to call somebody to ask them out. It took a little provoking. I had to be my aggressive self, but it all happened, and it's happily ever after.

But my point is, if I didn't go to yoga and meet these people who I would probably never normally just meet otherwise and talk to them, I would have probably not met my husband, which seems mind boggling to me, frankly, but it's true.

And my oldest son just moved to California a while back, and he just moved to a new part, and we had this long talk, like, go join a running club. And he's done all the things he learned. He's a quick learner, and he's done, you know, you do things that you love to expand this circle. And even if someone in this new running club is not your match, maybe they know somebody, and they'll end up fixing you up.

It's really about - the visual I like to give is, like, here's your circle. You need to, like, oh, like, there should be lots of other circles around your circle full of people you talk to that say you're interested in getting fixed up, because that is the ticket. I think in my mind, I agree getting to where I want to be.

Sade Curry [28:15]
I agree 100% like 100% because, and not just because you get to meet a lot more people also, because when you're looking at core values, when you're looking at who would be a match for you. Again, like the psychologist, social psychologist, say similarity and similarity of values is super important. Well, you're most likely going to find people of similar interests and similar values as add ons to your network versus the apps, which are useful. I think they're very useful. I have clients who've met their person on the apps, but they are more like a bar.

And so we have to be really strategic and work the algorithm. And we do all kinds of things like make it work so it's not super stressful. But when you're dating within your network and outside of your network, you're actually meeting - it's like who knows who. And so a woman will go to a dance club for the first time, when she got there, and she was like, it was all these older couples, like in their 60s, and no one was single. And I'm like, okay, the point is not for you, just like you said, is not to go to the dance class and meet your person, right? The point is to go to the dance class and meet people and create community and let people get to know you. Because guess what? Older grandpa and grandmas have, they have sons, they have nephews, they have cousins, and if they like you, they'll definitely introduce you to that son of theirs who's been single way too long, in their opinion. Right?

Heidi Friedman [30:00]
It's so true. And I just want to say I agree with you on the apps. In fact, one thing I always encourage people to go on the apps for when, even when they say, I hate the apps, I'm not doing the apps - and I don't mean like young kids, because I'm going to put that aside. I'm going to say people who are probably ready to meet the person - it's because it puts you in this open dating vibe mind.

I think some people, I just said this to a really good friend who had a bad relationship a while back and is starting to think about getting back out there. And I was very blunt with her, and I adore her. She's just one of my favorite people. But I was like, you have a closed vibe, you need to open your vibe. And part of the way you open it is just, I liked the safety of the apps at first. I'm very analytical. I can do my due diligence. You can Google them. You can look on the apps. You can kind of see what you can figure out. Let's make sure they're not bankrupt, they're not a serial killer, whatever the things are.

But then you can email back and forth. And I do think you get a feeling of whether someone's normal enough to go out with or whatever, in those emails. And so I try to make it not a quick fix, but an investment. And when you invest in that process, I just think, okay, tell yourself you're gonna go out with three app dates over the next month, and it just changes your vibe. It says, "Okay, I'm open to dating." It's almost like practice. It's, I say the same thing to my kid. Let's do a mock job interview before you do the real job interview, because you don't want to be unprepared. Preparation plus opportunity equals luck, and there is a luck.

Sade Curry [31:46]
Okay, when I think about the me I was - I was in the dating pool for 18 months, start to finish.

[31:57]
Pretty quick sister, by the way.

Sade Curry [32:00]
I feel kind of proud of myself, but when I think of the me that started out and the me that met my husband, we were very different. So I'm kind of like that deep dive rabbit hole kind of person, like when I'm ready to figure something out, nothing else exists. So that's kind of how I did my personal development after my divorce. And so I just kind of figured those things out pretty quickly.

But I remember early on, you're talking, probably the first month I was on the apps, one guy sent me, "hi, how are you" kind of just brief email? And I said I found the email recently. I was telling my clients about it. It was 700 words long. That was my response. So I'm so glad I got that out of the way. Now, of course, looking back, he was definitely not the person for me, like my husband is just so many notches.

Heidi Friedman [32:53]
Above that. So he went to me.

Sade Curry [32:57]
Naive, desperate, pick me energy out of your way very quickly. Those early guys.

Heidi Friedman [33:04]
Yes, exactly. You just, and you don't always say how you when people ask you, "Well, what happened in your marriage?" Or that's assuming you were divorced, or "why are you not married yet?" Or whatever it might be, it sometimes helps to practice and see what you want to say.

But at the end of the day, I do believe in authenticity, because I think every foundation of relationship has to be authentic. And I have a friend, Paula Edgar, and I was on her branding room podcast a little bit ago, and she was saying that she always gives her friends on apps a hard time because they're pretending to they're not being authentic. And she feels like you've got to revisit what you put on the apps and make it more authentic if you want to meet anybody that's worth meeting, that it's a very important thing. It's like not coming to social media, like, "oh, we look happy even when we're not." I mean, I think an idea, at least a general idea, of who you are, has to be out there.

Sade Curry [34:13]
This is my biggest pet peeve - the dating profiles. I have so much to say. People dating profiles, and actually end up I have, like, a $47 product, just for your profile, because I'm just, I'm horrified at it, but I realized we don't know how to do this. It's not - no one is doing it wrong, because no one knows how to do it right. And we're told, like, "okay, you gotta go on the apps, and now you've gotta say what men want," or "you've got to their rules," or "there's etiquette," and there are all these fake rules about how to be out there, but those rules actually don't exist.

And then if you have kind of low confidence, you can think, "okay, well, I want to do it right. I gotta say the right things." When what really - and data shows this. OK Cupid collected data on the people that were on the apps for a very long time, and their data showed that whenever a person had a unique feature, whether the feature was their ears or their hair, were like something that they might feel was something negative - if they leaned into it, like if they showed it off, like if they were fun about it, they actually got more interest.

Heidi Friedman [35:29]
Interesting on the apps, yeah, because everyone else looks the same. I do counsel the boys all the time here in our family, because they've showed me, as I've gotten into this relationship and dating stuff even more. You know, through the book, I'm just obsessed with the whole concept. I want everyone to find their happily ever after. But I'm amazed at sort of the hinge and tenders of the world and how that works right now. It's very different, frankly, than match.com or eHarmony or something back in the day, which makes me ancient, but, and I know some of those are still around.

But the problem, I think, for most people is they look at somebody and say, "Is he attractive, or is he not?" And they look at the picture, and then they're swiping, and you don't look at like, what does that person do for a living? Where are they from? What do they enjoy? And in fact, I think you need to look at all of that stuff first and then think about now, I'm not saying you should go out with someone you're not attracted to. That is not what I'm saying. There is chemistry that is essential to these relationships. But that being said, a first glance at somebody for two seconds doesn't get to what really makes a relationship. And so focus less on a look that you like, and more on what a person's about, and then maybe I'll get a little farther through the process, 100%.

Sade Curry [37:06]
And here's the thing you're not - this always blows people's minds when they get it. They hear it, but then they don't always get it. You're not even interacting with the person yet, right? Exactly? When you're looking at the profile, you're actually not seeing how attractive that person is or isn't yet. I have, if I don't know if you've ever had the opportunity to meet a celebrity in person, they are not as attractive as they look.

[37:34]
Very few always like to me, but no, it's always

Sade Curry [37:40]
Disappointing. I'm like, what is happening? I've been crushing on you forever. Any chance

Heidi Friedman [37:47]
I'd love to meet him, but, no.

Sade Curry [37:50]
I always tell my clients, interact with the dating profiles like you did, and I love that. I work with our generation with the phone book. The dating apps are a phone book. That's it, until you are on a phone call with the person, or you have messaged back and forth and verified what they said on their profile, did a video call, a FaceTime call, literally, you assume you know nothing about this person.

Heidi Friedman [38:19]
Yeah, that always helps. It's really important. It is, but you know, it's putting yourself out there, and that's what you have to do. And you put yourself out there in every way possible, and then you hope it happens. And sometimes you have to put yourself out there over and over and over again. But it just takes one person, and I always felt and when I probably got to some of my lowest points, I think one of the most significant things I said to myself is, what if the next date is him? And I would constantly say that to myself when I didn't want to go and I said, what if it is? And that's probably kept me going.

Sade Curry [39:08]
That's such a great belief. And it turned out to be, it got to the point where the next one was the one. So I'd love to hear like, a couple of your funny stories, a couple of your disappointing dating stories, and are these in the book as well?

Heidi Friedman [39:25]
So a lot of the dates are spattered throughout the book. One of the funniest situations I was in was actually I did Jewish speed dating. So my mother somehow convinced me to go to this Jewish speed dating. And if you haven't done speed dating, I don't even know if they do it anymore, but it's speed, right? You sit down five minutes. So it was at this bar. I went with this friend, and I walked in and I'm not trying to be overly mean, but for whatever reason, there was guys from 20 to 65 at the time. I was 45 maybe. I mean, I would say several of them lived at home with their mother, and I don't, it's not a Jewish thing.

Usually, I, at the time, was hoping to find a Jewish man, because I, again, like for me, that was important for others. It's not, but it was important for me. And the short version of that story is it was like, I couldn't get over it. And there was not one single person. I was like, I'm moving. Like, I'm literally moving. This is terrible.

Sade Curry [40:29]
I think we all said that. I said it too. Everyone is like, there's no one in my state. I'm terrible.

Heidi Friedman [40:37]
I was but, you know, we let that go. So, that was probably one funny. The other funny experience that I talk about a lot is just that I found a guy on match.com and I will say I did have two match.com relationships, situation ships, I would say, for several months, where I did date each of these guys, and they were guys that I would not normally have interacted with anyway. There's no way I would have met them and one was better than the other, but I grew from both of those relationships. And so it did serve its purpose.

But this particular day, I had gone back and forth and emailed this guy, and I met him in a bar for a drink, and I sit down, he doesn't look anything, I mean, like, he's bald, wearing like a turtle neck, and in the profile, like, in the profile, he had like, full hair and a cool look. It was like, not the same. I'm pretty sure it wasn't the same person. So I get there, we order a drink. Five minutes in, he brings out these papers that were called a cease and desist order, which was like from Pepsi or Coke to him, basically telling him that he had to stop doing whatever he was selling something illegally out of his garage, basically. And he wanted my legal advice to look at this and give him advice.

And I was so taken back. Now this is the time, as I say in the book, my kids were young, and I was like, "oh, my God, something happened. I have to leave." I was in and out of there in probably 12 minutes total. But it was just one of those ones where you're like, this is just a double whammy. So that was probably one of my funnier.

Sade Curry [42:22]
Oh my goodness, like they will stop at nothing.

Heidi Friedman [42:26]
They will stop at nothing. Yes, I had many more bad dates than I had good dates. So and I was not somebody - the other thing I might encourage people to think about, and this might be a contested belief, but I can't tell you how many times I'd go out with somebody once who was like lovely on paper. You know, I got fixed up once. This guy was a surgeon. He had grown girls. He was just like a lovely person. I had zero connection to him. On that first day, I could tell in the first five minutes he was lovely. He just wasn't my person.

And one of my girlfriends at the time was like, "you should just go out again. Maybe he'll grow on you." I'm like, "I don't need someone to grow on me. Like, that's not what I want. I'd rather be alone than have someone grow on me. So I already had someone grow on me. I don't need another one."

So the one thing I did do fairly regularly is if I went out - and sometimes I went out and I liked the person and they didn't like me, so fine. You know, it happens both ways. I want to pretend that I was always the one doing this, but sometimes I was asked out again, and I very clearly said, "You know what, I don't think we're a match, but I wish you the best of luck, and I'm glad I got to meet you." And I was very honest about it, and I didn't want to waste anyone's time, and I didn't want to waste my own time.

And I mean, I'm a single mom. I had two young kids, I had a busy law practice. I was not going out with someone again, just to give it a try. So I do think it's okay to make a judgment quickly, as long as you have an open heart and know yourself well enough to make that judgment.

Sade Curry [44:01]
Yeah, I like to say it a little bit differently, because you say that way and women run off, and I hear them say, "Oh, I know myself really well, and I have my intuition." I'm like, "Oh no, no, no, let's do this. It's okay to say quickly, when you have enough information, when you have enough data," which is exactly what you said, but I don't want to give - I talk to women about this all the time, and they're so slippery.

Heidi Friedman [44:29]
Right? I don't mean, like, make a judgment before you meet someone, or I'm always the one to say, well, just go out one time. I mean, you can't hurt unless there's some other reason that you don't want to. But if you really go and you have, it's not 10 minutes, and you really know afterwards, this is just not going to work for me, then I'm fine calling it a day. I mean myself. I'm also a little bit quick on judgment, sometimes for better or for worse, but I do feel like I'm a pretty good judge of character. So it sounds like.

Sade Curry [45:07]
You're a person who, whether you know it or not, you're collecting the data exactly. If I asked you, why did you say no to that person? You probably know why, even if you're not conscious. Like what I find is that women will have a feeling, right? And they will say no, and I'm like, "Well, why?" Or this is what's interesting about people who make those judgments without collecting data, is that in other situations, they will have the data and not make the judgment when they leave.

So I will find women who look at a man on the profile and "he's not as attractive as I would like," which is not enough information to say no, right? And to go be like, "Well, no, I kind of know what I want" and all that. However, when a man matches their esthetic, so he's super hot on the profile, and they get on the phone with him and he's disrespectful or flirty, which is data, they tell themselves, "Well, I'm gonna go and just see." And I'm like, "No, you need to flip that check to see how much information you have." And once you have enough information about whether or not this person is respectful or kind or decent, you say, No. And if you meet someone online and you don't have enough information yet, get the information. Like you might say, "Well, I don't want to go on a date. How about I get on a phone call? How about I get on a FaceTime call so that I can see if he is as ugly as he appears to be in his photos," that's okay. As long as you have the information, I'm good.

Heidi Friedman [46:41]
Well, and you have to be self aware of things. And I think sometimes when you meet somebody in person, they look different, they feel different. I've met so many - I've just told you a bad story, but I've had a situation where I wasn't so sure, and I met somebody, and I was like, "Oh, he's super cute." I mean, the first thing I texted Anne when she's like, "I want play by play when you meet Will," the night she fixed us up, and I was like, "He's adorable." That was, like, my big first impression. But it evolved, obviously, so much from that. So there does have to be like that good feeling, but you have to be open and not judgmental, and give it opportunity.

Sade Curry [47:35]
How did you handle this? You know, it looks like you were very open about your journey and your friends and family were all watching this what can feel like a very messy process. And I know a lot of women who hesitate to date because they just want to be able to go out and pick the right guy off the shelf and not have any mess, not have any bad stories or bad situations. And when I say bad, I don't mean unsafe. I just mean the guy moves out his lawsuit for you to look what you can look at. How did you handle just having life's messy?

Heidi Friedman [48:07]
I mean, I think anyone that thinks that looking for a life partner is not messy, or life's not messy is, I mean, a quick aside, Will, a couple of years ago, right after COVID, got breast cancer. My PSA is, men could get breast cancer too. I could not love him more for the warrior he was during that. And it changed our relationship for the better. But it's life's messy, but that's just an example of that.

But I would say I did two things. One is, I did not introduce a single guy to my children during my entire dating process, and I very much - people might judge me for this, and I understand there's single moms that didn't have the same level of help that I did, but you do have family and you have friends and other things. I just felt like my kids were not dating. This is not a play date. This was my own experience, and my son, at the time, was young, and I knew he would attach to any male figure, and I just didn't want any disappointment in his life, and I just didn't feel like he needed that. And so that's how, one way I manage it is I kept it very separate. So until I met Will, my kids had never met a guy that I had gone out with.

And the rest of it was, I will say I didn't bring dates to most - during that time frame, we were in the bar and bat mitzvah circuit, and I was invited to a lot of galas and stuff for work and things like that. 99% of the time I did not bring a date. And one of my other lessons was, I'm not bringing a date into my work situation or my real deep friendship situation until I feel comfortable doing that. There was one guy who I dated for a little while, and he did meet some of my friends and you know, but it wasn't in that kind of situation.

So I think you just need to make strategic choices and figure out what's the right thing for you. And I just had to put up those boundaries so it decreased my stress level. I wasn't someone who felt like I'd rather bring a date just to have anyone. I was missing the my gay best friend at the time who I have now that I would bring everywhere with me, married, but he maybe would have gone with me anyways.

But it's just, it's one of those things that you just have to figure out how to be comfortable in your own shoes. You are your best date, and you have to know that and feel that. And so I did put those walls up in certain places to make my life a little less confusing.

Sade Curry [50:57]
I love that, and I did the same thing with my kids too. The only man I dated that they met was my husband. I dated other people, and I was just like, nope, unless I'm sure this is the one. And even when he met my kids, he met them a little earlier than I would have liked, at four months. We had been dating for four because we were going to see Hamilton, and my daughter loved Hamilton and hadn't seen it like she knew the sound. And I was like, I can't go see it without her, so he has to meet you early, earlier than I would have liked. That's how that happened.

So with Will, how did you know he was the one? I mean, you had dated all these guys, you'd been divorced. What was it about him that was different? And when did you know that this is your person?

Heidi Friedman [51:44]
I would say I was suspicious after so our first day was supposed to be a drink. It was like, then it turned into dinner, and the whole thing we and it was one of the first times I wanted to stay rather than leave. So that was a positive sign. But there was just this natural connection from the beginning. And I think, to be honest, we came from very similar past marriages. We were raised very similarly. We have very similar values and belief systems. He was CEO of our port authority. He had a very big, important, politically high profile job. He understood my job.

And so we just, I had two kids, he had two kids. He's the primary parent for his two kids, as am I. So we just had all of these similarities, and it just became natural and easy to talk to him about anything and everything. And it was funny, because he hadn't been on a date in 24 years. I was the first person he dated. And I kept saying to him, "Are you sure you don't want to date other people first?" And he's like, "I'm good. I heard all your stories. I'm perfectly good."

So that part was a little bit funny, and I'll never forget, we went away, like, four weeks after our first date for his birthday, to Columbus, which is like two hours. And my friend Anne, who fixes up, was having a heart attack, like, "it's too soon, it's too soon," but we told each other we loved each other that weekend. We've got rules again in there, and it was just - and maybe it's because I had been on that journey that I was so sure.

And I wish I could tell you like there was something I knew, but it was, it was, I think where we were coming from brought us to this space that worked so well for each other. I think we're both kind of have a helper personality. I think we're both intellectually curious. He's more intellectually curious than I am, and while there's differences, like he's off rafting with his high school friends this week, living in a tent like literally my worst - if you want to make me, like, punish me, make me do that. And he doesn't - he hates yoga, so it just, you know, we still have things that are not our together things, but we have so much together.

And so I just am grateful every single day. And he's the first person I want to tell anything. And my very best friend and everything else in between. And so it's been, I can't believe it's been 10 years we've been married, because at the same time it's like, doesn't feel like that. But then I don't remember my life without him. So I will say I do think my stomach and gut was tuned up to tell me what was right by then, though. So when I say, just this perfect feeling that you know it's right. I didn't have a single doubt on our wedding day in my head whatsoever like none.

Sade Curry [54:52]
I know what you're saying, because people talk about their intuition, right? And I say, like, has your intuition been trained with the right data? You know, if you've only dated your ex and you haven't dated at all, your intuition is not necessarily broken. It just doesn't have enough data. Because intuition, in my opinion, is just pattern recognition, and you have to see a ton of patterns to be sure that you recognize a pattern when you see it. Right? Otherwise it could still turn out to be one thing or the other. And so therapy helps. I'm a big fan of therapy too - a lot of my clients are in therapy and working with me, which is so helpful, because then sometimes when we're in a coaching session, I'll be like, "so what did your therapist say about this?" It's important.

I absolutely love your story, and I love that you mentioned that you have different hobbies, because you will be surprised at how many people will look at a dating profile - they don't like camping, they see he likes camping. And they're like, "no," and I'm like, "no, you don't have to go camping."

Heidi Friedman [56:04]
With him. When you're an adult, no one can make you go camping. That's one of the best things in life. So, and I do say this in the book a little bit - he's a jam band guy, not my favorite thing. Well, I go to a Grateful Dead concert with him? I absolutely will to be a good wife, but it's not what I prefer. I coffee house on serious Kind of person. And we do have separate things. I mean, I finally got him to go to Pilates. So we have some shared things too. I mean, we work out with a trainer together, we love our walks. There's so much that we like to do together, travel, lots of things, but we also have independent interests. I mean, he goes out in a kayak all the time. No, thank you.

So you don't have to have everything align. But I do think how you look at the world should align and where you want your life to go. You know, like, if you're not a traveler and never want to leave where you are and the other person's a traveler, that's a problem. Like, those are the kinds of things. But otherwise, he can go be in his tent, and I'm here this week, seeing some friends and doing some fun stuff.

Sade Curry [57:15]
Yeah, you can't tell the things that matter from a dating profile. Like, you're just not going to be able to tell. I mean, you can tell - there's some people that are clearly jerks from their profile, like those people, with photos and all they have the eggplant emoji running all across their profile. They're probably not for you.

Heidi Friedman [57:36]
Thank God my profiles were pre eggplant emoji. I forgot about that. Although I did get some bad pics sent to me and messages. So it did happen back then, too.

Sade Curry [57:50]
You're like, yeah. I think they've gotten a lot better now, thank God at filtering those things out, but they still happen, especially if you've exchanged numbers and things like that. But oh my gosh, Heidi, your story is so fascinating. I cannot wait. I started the book. I have not finished it, but I cannot wait to read all of the stories. So I don't know if the camera is gonna flip this, but for those of you watching on video on YouTube, this is "Love Lessons: 104 Dates and the Stories that Led Me to True Love" by Heidi Freeman. And I highly, highly recommend that you get the book. It's available on Amazon, I believe is where I go.

Heidi Friedman [58:30]
Amazon, Barnes & Noble, Good Reads, all of those. Be great. Thank you. My newest endeavor is I started a podcast called "I Love You More" with my 22 year old son, Zach, and we're talking about all things love, dating and relationship and the generational differences are fascinating. I love hearing his perspective. It's on Spotify and Apple podcast. We have a few episodes out, and we'd love you to listen and follow.

Sade Curry [59:01]
Absolutely and the link to the book will be in the show notes. The link to the podcast will be in the show notes. And if people want to just connect with you, send you a message, say hi. Where is the best place for them connecting?

Heidi Friedman [59:14]
With people? So at love lessons 104, is my Instagram. You can DM me there or email me at love lessons 104 at gmail.com.

Sade Curry [59:25]
Amazing. And so the Instagram will be in the show notes as well for anyone who wants to connect. Heidi, oh, my God, thank you so much. Thank you.

Heidi Friedman [59:33]
The way you spattered data and analysis and findings into our conversation was riveting. That's my favorite thing. I love that stuff. So thanks for sharing. I learned a lot from you today as well.

Sade Curry [59:48]
Oh, my pleasure. My pleasure. All right, we're gonna wrap up. But is there any wisdom, any advice, any tip that we didn't cover, that you're like, oh, people have got to know this, and you just want to throw it out there?

Heidi Friedman [1:00:00]
The only thing I would say is, it's time to spread more love in the world. The world needs it right now, and so I am making it my personal mission to do so. And I just always say, like, think about who you love, who's - whether it's romantic, professional friendship, just tell someone you love them. I think right now is a good time to keep spreading the love.

Sade Curry [1:00:22]
Oh, so good, so good. We really, really do need that. And there's so - romantic love is not the only kind of love. No, there's all kinds of love.

[1:00:30]
Lots of connections, lots of connections. Thank you. Connected to you.

Sade Curry [1:00:34]
Yes, same here. All right, listeners, we want to thank you for your time and attention today. It has been such a pleasure. I hope you enjoyed this episode as much as I did. Thanks for being a listener, and we will see you next time.