108. 104 Dates: A Midlife Journey to Authentic Love

Is true love still possible after 40? Heidi Friedman’s remarkable journey—from her divorce to dating 104 times over ten years—reveals a transformative path to authentic connection and genuine partnership later in life. Drawing from her extensive experiences and interviews with happily married couples, Heidi shares inspiring insights and practical wisdom for anyone navigating love in midlife.

In this candid conversation, Heidi discusses how therapy helped her break patterns and become her own best date before meeting her husband. She recounts hilarious dating disasters—like the date who brought legal documents for her review—and meaningful lessons about what she truly needs in a partner. 

Her guiding mantra, “I will be alone before I be with the wrong person,” ultimately led her to discover heartfelt, lasting love.

Highlights & Key Takeaways:

• Working on yourself first is essential—self-love and confidence attract the right partner.
• Dating with confidence involves an open heart, multiple avenues, and setting realistic expectations.
• Approaching dating apps with patience and proper screening can lead to meaningful connections.
• Becoming your own “best date” prepares you for genuine, fulfilling partnership.
• Boundaries and taking breaks are crucial for personal growth and clarity.
• Never ignore red flags—trust your intuition over chemistry or fleeting feelings.

Heidi Friedman Bio

Heidi B. Friedman, formerly Goldstein and born Eisman, is a successful attorney and partner at a large law firm specializing in all areas of environmental law and environmental, social and governance (ESG) based counseling. Love Lessons is her first book, but Heidi has written related to her professional life and experience as a female lawyer.

Heidi lives in Cleveland Heights, Ohio, with her husband Will, and has four children. Two children she birthed, Morgan (25) and Zach (21) and two are her bonus children, Max (28) and Ben (26). In her life, she has a strong network of amazing women who she treasures and who provide support, guidance and company for drinking wine.

Find Heidi Online: Instagram, Website, Buy Book (Amazon)

Chapters

• 0:00 Finding Love in Midlife
• 5:14 The Birth of "Love Lessons"
• 10:22 Dating with Confidence
• 16:36 Navigating Blended Families
• 22:01 Learning to Be Taken Care Of
• 29:33 Modern Dating Across Generations

Transcript

Speaker 1: 0:00

If you find yourself divorced or single and wondering whether or not you can rediscover love in midlife, then today you're in for a treat. On today's episode, I'm joined by Heidi Friedman, a divorced mother of two who found herself in the middle of midlife wondering hey, does true love even exist? So, determined to find the answer, she immersed herself in research and dating 104 different dates over a 10-year span, and let me tell you that turned into a book. She's the author of Love Lessons 104 Dates and Stories that Led Her to True Love, and so we're going to jump into her journey today and find out all the things you ever wanted to know about finding true love in midlife. Heidi, welcome to this Emptiness Life.

Speaker 2: 0:45

Thank you so much. I am so excited to be here and to join you and your listeners to chat about love lessons.

Speaker 1: 0:51

So we were talking a little bit beforehand about there are different components to love life as the kids grow. But I wouldn't be a good host if I didn't ask this first question. You said 104 dates in 10 years. Seriously, 104 dates.

Speaker 2: 1:06

Seriously 104 days, not 104 guys, it was about 55 guys.

Speaker 1: 1:11

People will be wondering that question 104 different people. How does that even possible?

Speaker 2: 1:14

Yes, it is the number one question I get. So there was three or four guys who I dated for some period of time. My youngest son taught me the term situationship, which is, like you know, not definitely not equivalent to a relationship, which none of them really were, but I did count those dates.

Speaker 1: 1:34

Yeah, situationships that's, I think, a new term for folks especially you know, our age like Gen Xers and people who are in midlife and maybe empty nested. I know some of the younger coaches out there who deal in relationships. All they talk about is situations.

Speaker 2: 1:48

Right, exactly, exactly. So I'm learning as I go.

Speaker 1: 1:52

Well, hopefully not now. Now you're remarried, right yeah, so hopefully that kind of life is done.

Speaker 2: 1:56

We just had our 10-year anniversary so all is good.

Speaker 1: 2:00

Tell me about the book itself. It's a really intriguing title for me and for my listeners, who it's like, hey, they find themselves in midlife maybe never married or having had, like this, you know, what they thought was a great marriage. And then the kids go off to college and then I've talked about it on the show before Gray divorce happens and people are kind of like blindsided and they find themselves wondering ooh, is this it so? Is it? Clearly it's not about your journey.

Speaker 2: 2:29

It's not. It's not. And I just had a friend go through literally exactly as you described and she read the book and she was really said. I gave her hope which is all I'm trying to do spread some love and give some hope.

Speaker 2: 2:42

So the book actually was born around my 40th birthday, because I had woken up on my 40th birthday and I had been divorced for several years and had decided okay, I don't know why, but I don't think I have ever been truly in love which you can judge me. I was married, but it was a different situation, not that sort of partnership, deep true love, that where you're totally madly in love with someone. And so I started interviewing friends who I thought had what I saw, as you know, idyllic marriages, or at least they like, really loved each other, you know. And my questions were how did you know it was your person, you know. And my questions were how did you know it was your person? How does it keep? How does he or she keep you happy? What is the best part of your relationship? All of the things.

Speaker 2: 3:32

I never talked to a couple together. I always talked to in, like the husband and wife individually, if I talked to both of them, because I only spoke to people who I had pretty significant relationships with, because I was really looking for people that I thought had figured it out. And so I'm an attorney by day and I was traveling all over the country at the time doing depositions and on planes. I would look at my notes from my meetings and I realized after some time that it was the same themes were popping up over and over again and I so I wrote about eight chapters and with some of those themes, and then I parked it because I had started to got to the point, actually, that I kept hearing the same things over and over and I sort of was like, Okay, well, I figured it out.

Speaker 2: 4:20

So I now I know what kind of these themes are and I continued to date and then I actually forgot about the book. I met my husband in 2013. And then I had found the book, maybe about three or four years ago, and I was like, wow, it'd be really interesting to think about my current relationship, how it applies to these themes, think more about my dates and just my journey. And I honestly wrote the book 1000% for our four kids we have. I have two kids and two bonus two kids that I've birthed and two bonus children, all of which are adulting at different levels, from ages 22 to almost 29 now, but I have seen some of them in what I would call not the best choice relationships and I really wanted them to learn from my mistakes and not settle. So that was how the book was born and really the reason why I ended up writing it.

Speaker 1: 5:20

I love that so much For people who are listening. We talked about finding love in midlife and they're like, oh, but that was you know, you were in your late 30s as opposed to being in your 50s. But I feel like everything we're going to talk about today applies no matter where you are, in what stage of life.

Speaker 2: 5:35

you could, you know, connect with me at the end and I have gotten emails from super random people, even married couples, who said that they used it as a tool to kind of re-monitor and re-evaluate their current relationship, and they found it super helpful. And I've definitely. I've done a bunch of book signings and I've met a lot of, especially women who are in midlife or even a little bit beyond. I just had a 70-year-old reach out to me who's dating again for the first time. So there's hope for all of us and it's just a matter of putting yourself out there in various different ways and I think everyone can find love again if they really want to.

Speaker 1: 6:19

You mentioned your son, talked about situationships, but younger folks talk about red flag, green flags and yellow flags and their relationship. Have you learned about those two? And then did you find those in your journey of these 104 dates?

Speaker 2: 6:33

There was only the red flag concept back in my day. These other flags are sort of new to me. I definitely had a lot of red flag dates. I think the number one question I get is you know what was your worst, craziest date? And there were so many that it's actually hard to pick. I think what happened is when I started my journey, I was not very confident personally but I was confident professionally and I kind of grew over this 10-year process into someone who is much more confident, much more able to tune up my gut and find the red flags and therefore look for the waving green flag at the end of the day which are sometimes hard to find.

Speaker 1: 7:17

That is true. I would imagine as part of your journey, you worked a lot on yourself. First, is that fair? Worked a lot on yourself first, is that fair?

Speaker 2: 7:23

Absolutely. I talk a lot about therapy. I'm a huge fan. I've made my children huge fans. I think I had a lot to unpack and I learned a lot through the process, and I think I truly do believe that each relationship, even if it doesn't work out, teaches you something that you can take with you on to the next relationship, and you just sort of have to figure out what it is, and sometimes, when you're knee deep in it, you can't see it, but when you get some space from it, you look backwards. Then I think it comes to life and tells you what that lesson is, that you can carry on as you kind of move towards what maybe and hopefully would be your sort of true love or your person.

Speaker 1: 8:04

Let's say, you work on yourself a little bit and then how do you, or how does someone, date with confidence? What does that even look like?

Speaker 2: 8:12

You know it's hard. I will be honest with you. First of all, I think you have to have an open heart and be ready to date. I did a book thing last week and I had someone come up and ask a question and she's still trying to get out of an old relationship but also doing all these things and I basically said until that chapter is closed you're not going to have this open heart and open vibe. That until that chapter is closed you're not going to have this open heart and open vibe.

Speaker 2: 8:42

And I actually, as much as I also hate the apps, I love the apps because I think it's a safe way to put yourself out there, as long as you have low expectations.

Speaker 2: 8:47

My 22 year old will tell you the apps are just you make him crazy and he has a love-hate relationship with them and I think those kids that age have a different dating philosophy.

Speaker 2: 8:57

But I think for older folks in our middle age and above that, it allows you to safely you can do due diligence. You can Google people, look at social media, make sure they're not serial killers or bankrupt or whatever you want to check, and you can email back and forth until you get comfortable and then you just go with like make maybe I'm making a new friend. This is not going to be the love of my life, but it just gives you practice. Like I always say, would you go into your dream job interview without doing prep work and prep interviews? And so I look a little bit at online dating and people haven't met their significant other, so I'm not poo pooing it if it happens, but I think if you go into it more as a training type thing, it works. And then I also think you just have to tell everyone you know and I don't mean like your little circle of friends, because that's your circle you have to grow that bigger and wider, bigger and wider.

Speaker 2: 9:58

I'm a huge hot yoga fan and it kept me sane through being a single mom and a divorce and stuff and I'm in the front row always because I'm a type A have to stare at the wall to like be focused kind of person. And I was next to the same three people all the time on the weekends and we became friendly and rushing ahead to the end of the punchline. One of those people who I hardly knew and basically took a couple of years to even say hello to, fixed me up with my husband, who she didn't even know that well, but she worked with him and just thought of me every time she was with him and she has wonderful intuition and she definitely did a better job fixing up than many people. I had some bad fix ups but it was about, you know, telling people outside your circle, like through running club or yoga club or pickleball or whatever people do these days.

Speaker 1: 10:45

I love that. So like from hot mess to hot yoga to hot love, right Like that's.

Speaker 2: 10:52

Exactly, it was a transition.

Speaker 1: 10:54

Yeah, what was the biggest transition for you on that journey?

Speaker 2: 10:58

That's an interesting question. I honestly think that after a while of being single and being a single mom, I'm a super independent person. Anyways, I've always been able to support myself. I was one of the lucky people. When you know, the choice to divorce was mine. I was able to support myself and my children, so it was much easier, and I have extensive sympathy for women who are not in that same situation and I help and talk to those women quite, quite often.

Speaker 2: 11:28

You can imagine, after so many years you kind of develop this lifestyle and independence that I almost thought I'm never going to be able to fit somebody into this equation anymore because I got so used to uncomfortable kind of being alone. I had definitely decided that I will be alone before I be with the wrong person, even though I kept trying. So I think, like figuring out how to integrate someone into my life although Will made it very easy. He's my husband and then of course, one of the things to think about is at the time he had two boys who he was still caring for and the primary person for, and we had to integrate these kids and that transition was really hard. We were much slower with that than we were introducing him to my kids, although in my 10 years of dating he was the only introducing him to my kids, although he I.

Speaker 2: 12:17

In my 10 years of dating he was the only person I introduced my kids to. So I was not. I'm a huge believer in it's not a play date. I think I say in the book, and at the time my little guy was 10 or something. You know seven, eight, nine, 10. And I just knew he would be, like you know, a magnet or glue to whatever guy was in his life, and so I was really careful about it. But that was a really tough transition and I would never give up our now like extended, beautiful little combined family.

Speaker 1: 12:47

But yeah, for those people who may be going through that, let's dig into that a little bit more. The work piece of finding true love when it is a blended family you know it's really, it is sensitive, it's hard.

Speaker 2: 12:59

Someone told me it might have even been the kids therapist that it on average takes seven years for a blended family to feel like a real family. I think we were overachievers not to brag because it was, it was. It was a beautiful thing. I mean, my youngest, who's 22, is besties with Will's oldest, like literally talk all every day, but they're also like both obsessed with basketball and you know certain family guy and certain things that they're very interested in. But we were super careful, like when we came together physically into the same house, which was about a year after we were together physically into the same house, which was about a year after we were together and a year before we got married. We made sure each kid had his or her own space with a bathroom and a bedroom so that no one was on top of each other. We tried to treat everybody equal. It was a unique situation for us because we're both the primary parent for the children and so we had all the kids with us all of the time. So I think in a lot of relationships you have time as a couple or back and forth, and so we didn't have that. We went.

Speaker 2: 14:05

I went from being a mom of two to, you know, being a bonus mom to two others who like and at this point I mean my step sons are my everything. I can't even imagine them not in my life, but I think you do have to give them time. It took one of the boys longer than the other one to kind of embrace me, and I think you just need to push, especially if there is another parent in the picture, that I'm not here to replace that parent, I'm just. My true philosophy is you can never have enough people that love you, and especially nowadays. So I kind of feel like the more people that love you the better. And so, you know, just trying to get that point across. And eventually you know we got there, and now I feel like we were all in Mexico for Thanksgiving and I was like just looking around our table, thinking like I just love this family that we built which is something that's really special.

Speaker 1: 14:57

I love how it came together, and that might not happen for everybody, so a little disclaimer for people who are going through this right it doesn't always work this way, but you also have to work at to make it work.

Speaker 2: 15:09

A hundred percent. There was again lots of therapists involved and you know some some, you know mess ups I'm trying to think of the right word, I didn't want to swear, but some things that like didn't go as we hoped. But I also say like, which I talked to a lot of women about. I do think if you have adult children, like truly you know, if I met Will now and everyone's out of the house, I actually think as much as you want everyone to come together. It's harder, actually, because our kids growing up in the same house, even if it was only for five or seven years, made a huge difference and I think it becomes a little bit less important to be completely integrated as you get a little bit older and your kids are older. It's lovely and hopefully your kids want you to be happy and welcome whoever your new significant other is, but I do think at a certain point it becomes less relevant.

Speaker 1: 16:02

Yeah, for sure, and a little bit, probably more ingrained into like, oh, they're really a part of my life because I'm an adult and I've got this going on over here, right, what's one thing you learned about yourself through this journey.

Speaker 2: 16:11

What's one thing?

Speaker 1: 16:12

you learned about yourself through this journey.

Speaker 2: 16:14

I learned that I actually like having somebody take care of me. And this is I say this because, again, more therapy, no-transcript, basically make sure this was the right choice, even though I knew in my gut that it was. And he did all this testing. He was actually an excellent therapist, but he basically said, yes, you should get divorced, which is funny, but anyways. But he told me afterwards, because you meet with him individually is like, I'm not sure I know what you're looking for in your life, this true partner.

Speaker 2: 16:54

I'm not sure you'll ever let anyone in enough to be able to, like, take care of you, like you're saying, and that just stuck with me. I mean, it was so many years ago and I it's, it's the most beautiful. We take care of each other. There's, you know, my analogy in the book where, like, one of the themes is that really strong couples take care of each other. And, like, the analogy is when there's waves like, like, if someone goes under, someone pulls up, and you can't always be the puller upper, you have to take turns pulling each other up, because if not, you know you're going to either be exhausted or drown, basically. So I just we have this wonderful balance of supporting and pulling each other up. I give up like free control to him, because I trust him so inherently, and so that was probably my biggest revelation that I was capable of and what a revelation.

Speaker 1: 17:43

That was to be like thinking perhaps maybe you could never fully give of yourself to someone to take care of you, to be all the way like 180 degree turn to say, oh my goodness, yeah, it is amazing to have someone care for you in the way that you deserve to be cared for.

Speaker 2: 17:59

Totally, totally. I'm always sort of the caretaker, so it's such a nice feeling to have that, and so that was definitely that was a journey to get there for sure.

Speaker 1: 18:12

What's a funny story along this journey. I'm sure people want to know that too.

Speaker 2: 18:15

All right, I'll give you one funny. I have several of them. I actually have many of them, but one of the funniest ones is I was actually a matchcom day back in the day was sort of like matchcom, eharmony and like J day. But that J day was just terrible. As a Jewish woman I was like, oh God, this I'm just. If this is all that's out there here, we're in trouble. But and I found this guy on Match and we had been emailing and it seemed fine. We were meeting at a bar for a drink.

Speaker 2: 18:42

I always tried to like make a date you know short, like not a first date, like not a whole dinner, not like you know some kind of you know short thing, whether it's coffee or a drink or whatever.

Speaker 2: 18:59

It was easier at the time for me to have like some alcohol as I was continuing to try to move past this. But I show up, he doesn't look anything like his picture. Like, literally, he had hair in his picture. He was completely bald, he was wearing some random turtleneck, something I don't know, that's all I remember. But we were there for five minutes and he pulls out what's called a cease and desist order, not, and that he had gotten it from Pepsi because or Coke or something like that, because he was selling stuff out of his garage and so he wanted me to look at it as a lawyer and give him legal advice. And this is the time where you're like, oh my god, thank God I have young children and I was like, oh my god, my daughter's playing and I was, I think I was in and out of there in eight minutes and like running to my car, it was just.

Speaker 2: 19:46

It was like, you know, just one of those things, that. But that went so badly and part of it was just he wanted like some expertise rather than had any interest in me, but just generally. And then he texted me and asked me to go out again. I was like I'm good, we're good.

Speaker 1: 20:02

It's like legal aid turns into like legal right, you know exactly exactly. So for the people who are wondering out, there is like you have found true love. Have you? In the course of your research or talking to other people? Is it like? Have you found folks doing the same thing in midlife? Like finding?

Speaker 2: 20:21

their person, absolutely. I have a couple of friends who are on a second marriage, some of who I interviewed the book, some of who I have not, and they have definitely found their person, who they say was more of their person than in the first marriage. Because I also feel like, I mean, who I am at 45 is very different than who I am at 28 or whatever, and that's why I'm also telling my kids to like, take your time, you do not have to get married by the time you're 30. Like you know, let's figure out who you are and what you want and and all the things. So but but yeah, I mean, and I will say, the vast majority of people that I interviewed for the book the first time, I think only one of them's gotten divorced since I interviewed them, and those are some like there's some serious longevity in those marriages, but I do, I've sort of become like I think when you're, like the first person divorced and I'm a lawyer, anyways, I talked to a lot of women who get divorced, so they might be 30, 40, 50, 70.

Speaker 2: 21:21

I talked to someone 70 last week. You know, it just depends, but I help them. Try to understand. You're at the bottom of this hill and you're going to get over it and it's so beautiful on the other side and all of the things. But you also want to get hope that they're going to be able to find love again, if that's something that they're going to be able to find love again, if that's something that they are interested in, and so I think I'm a symbol of that for a lot of people, which I really appreciate, because I always say everyone needs a will, which is my husband's name, and they should all have a will in their life.

Speaker 1: 21:49

Everybody should have a will. Wait, not that type of will, this type of will. This kind of will exactly Throughout this journey, other than finding will what was a defining moment for you.

Speaker 2: 22:03

I think that I originally, right when I got divorced, I started dating somebody and it was symbolic of some of my bad choices. He turned out to have a drinking problem and it was somebody that I think I did meet him online. Actually, I only dated like two people that I had met online, but I had. I met him online and he was a lawyer and we definitely clicked. There was like chemistry, it was like one of those things.

Speaker 2: 22:34

But I found myself overlooking these bright red flags. I found myself overlooking these bright red flags and, like, I even found out later that he had told me he was divorced but he was really only separated, and so, you know, I was. I was strong enough to like end that and walk away pretty freaking quickly, like compared to before, but I definitely felt that was a defining moment. I'm not going to just find somebody, even if there's chemistry there, if the other pieces of the puzzle are not there for me, and I know what I need now and I need to be careful to not go down that bad road again, and so that was really a defining moment.

Speaker 1: 23:13

That was probably like a year into, maybe two, into being divorced, and I was like, okay, like a year into, maybe two, into being divorced, and I was like, okay, yeah, so where my, where my coach brain goes for my listeners is you? You needed to work on yourself first before you could figure out what you want and you just hop right back into the pool of what wasn't working Exactly.

Speaker 2: 23:29

And then I also realized I need some sort of perspective. I mean, I definitely took over the 10 years I took lots of breaks from dating. There was many times where I'm like I'm not dating anybody for six months, I'm just focusing on me and my kids. And I had busy times at work when I was traveling a lot and all of that, and I kind of took breaks from the process. And I would say the other defining moments were me. For example, my oldest was Bob Mitzvah, bar Mitzvah ages.

Speaker 1: 23:55

We were kind of in the whole thing.

Speaker 2: 23:59

So I had to constantly go to these things by myself. I would never bring a date with me with my kids anyways, but even without my kids like to work thing, this it was like too stressful to me and I never was really in a relationship where like it had reached the level of, okay, we can do this. And so like showing up alone all the time and like being the odd person out really made me kind of assess my life but also realize like, okay, I'm on my own best date and I can do this. And I had lots of hysterical dating stories to share a cocktail hour. So I was very entertaining and you know, I just I found that every time I did it it got a little bit easier.

Speaker 1: 24:38

You just said a nugget in there which I want people to like go back in here is I was my own best date, and I think that's how you become the best version of yourself. For other people is to become your own best date, and then you can figure out how other people fit into that Exactly.

Speaker 2: 24:53

Exactly I really I wanted to be. I did feel like when I met Will that I had become the best version of myself by that time. I'm still learning and growing. I actually think he makes me. One of the things I say in the book is he makes me a better person. Like he's such a good person and he's expanded me culturally and like with arts and all kinds of stuff that I feel like you know makes me a better person. He was so encouraging to write this book or whatever it is that I want to do in my life. He very much supports me and I see him always doing well and doing good and all of that and it makes me want to as well. So it's fun to grow together.

Speaker 1: 25:32

It's interesting that you bring that up. I was just searching for a note that I wrote for my daughter. I was watching a movie, right, all the good things come from movies. It was about finding the right person and there were four questions to ask Is he kind or is she kind? Can you tell him everything in your heart? Does he help you become the best version of yourself? And then the final one is can you imagine him as the father of your kids? But that plays out too, if you're a blended family, like a supporter of your kids, let's say.

Speaker 2: 26:03

But I thought those are easy. Four questions, those are fabulous.

Speaker 1: 26:06

And so my daughter's 25. My son's 27. But I was like oh, I'm writing those down and tucking those away for later. I don't think she listens to this. Oh, she's not going to hear those now.

Speaker 2: 26:23

Well, tell her she's got to read my book because it drives my book very well. I totally will. I'm actually surprised about how many of my friends you know we all sort of have adult. I have tons of friends who have the kids the same age as our kids and so many of them have bought the book for their kids and I've heard from so many of the kids and because I think they hear me my kids talk about how they've learned so much from the process and things like that.

Speaker 2: 26:39

A friend of mine uses this term, noah's Ark theory, which is kind of the thought that in our world everyone feels like you have to be matched up in a paired up, and so you kind of have this inclination like it's better to have someone in my life rather than to be alone.

Speaker 2: 26:57

And what I'm trying to tell my kids is, first of all, you're not ready to be a partner until you're your best version of yourself. Like for Valentine's Day this year, I sent them all $100, all four of them and I said take yourself out to do something yourself and focus on yourself for at least an hour, because you are your best Valentine and you're not going to be able to be a Valentine to someone else until you do that. And so they're all excited about the money, of course, but still I think they got the message. And so the goal is like for the kids to understand that they don't need to fall into this. I need, need a partner, I need a date, I need whatever. They need to focus on themselves, you know, put your mirror on yourself, and then we can go towards that once we're ready to be there.

Speaker 1: 27:41

That's such a great point, heidi. I'd nail that into my daughter's brain too. It's like you don't need somebody else to complete you right yourself first. Then you find somebody who compliments you doesn't complete you compliment oh, I like that too.

Speaker 2: 27:56

We'll have to alter the theorem.

Speaker 1: 27:57

You compliment me instead of you completely. Yeah, we'll have to have them rewrite it exactly. Vacation exactly together my wife and I and my daughter son is not a beach guy, so he's like, nope, I'm out, but I'm gonna get that book and bring it for the beach so she has some noreen. I'm like listen to this podcast episode first and then I've got something for you Perfect.

Speaker 2: 28:18

Perfect and it's been fun.

Speaker 2: 28:20

I started a podcast with my 22-year-old and he's done podcasts before, but we're calling it I Love you More.

Speaker 2: 28:29

It's available on Spotify and Apple and we're talking about all things dating, relationships and love generationally and I will be honest that it's brought me more joy than anything I've ever done in my life just having these super in-depth conversations with Zach. But at the same time, I have learned so much and just how you know the way these kids will approach people on Tinder or Hinge but not walk up to them at a bar, I mean, and it's just how swiping's almost can be a game sometimes and it's just this. It's just a very. I mean I've learned a million things, but it's just been this interesting journey and I am learning a lot and I think that modern love and modern dating for our kids looks different and I actually am like promoting to my four like let's date in the wild people, like let's delete the apps and let's put yourself out there and do things because you know maybe meeting people will actually be good for you, like in real time.

Speaker 1: 29:33

Exactly. Forget the swipe left and swipe right. How about you know? Be right in front of somebody instead? I love that. So I do have some younger listeners who listen to the show. I'm just curious what are the main differences that you and your son talk about on that?

Speaker 2: 29:50

show so far. We just started it and he's graduating next week, so it's a little bit on hold for a minute. But you know, the main difference is literally, I would definitely say, the technology and I would just say the number of apps and how they're formatted. And we just talked a lot, you know, like what you have to put in and how people are trying to cultivate a vibe rather than authenticity trying to cultivate a vibe rather than authenticity and we've talked a lot about the fact that being authentic is really the foundation for a strong relationship. So, in my head, meeting somebody online like that, when you're not being your true self, is very challenging from like a foundational standpoint, and you know he definitely agreed with that.

Speaker 2: 30:39

We talked a lot about fix-ups, I think last episode and that and you know they're not remotely into that whole thing, I mean.

Speaker 2: 30:45

But he's 22 and even my 25, 27, they've never really been fixed up and and I was, so I said I think I asked him last time would you let me fix you up?

Speaker 2: 30:56

And he's like you know, maybe I do think that they might want to trust like people in their lives, to maybe fix them up at work or in other places and see how that goes. I do sense, though, that there is this kind of burgeoning joining and like turning away from the apps, and I think that, hopefully, leaving college will will change that, at least for like my baby, and hopefully for others, and so you know, it's also I think there's a lot of learning that they're trying to do like. Zach was basically explaining like I'm 22, I'm not the best version of myself. He's a super self aware kid, and he was saying that I know I'm not ready to be in a relationship, I know I've made wrong choices, and so I feel like, even if I dated somebody now, it wouldn't be my person forever, and so I might, when I'm ready for that, I might approach it differently than I do now, which makes total sense.

Speaker 1: 31:56

Yeah, you know, I think too it's probably a little bit different for folks. You know the younger kids, right like for us. I was, like you, met people through your circle of friends, which is small, or at a bar right, right. The kids are like so true like even alcohol is less of a thing now, right, yeah?

Speaker 2: 32:13

100.

Speaker 1: 32:15

Remote work plays into that yeah that's a huge.

Speaker 2: 32:20

You know, I didn't think about that. That's a really big point.

Speaker 1: 32:23

They have to turn to the apps. But you know, at the best solution yeah, it's part and parcel of everything, a little bit of both. They're like a really good recipe the apps, meeting people going out there and just talking to anybody, those types of things. So that's, I think that's how you find, after 104 dates, true love.

Speaker 2: 32:42

Right, it's like a little bit of everything. Exactly that's what I say. I mean, you really have to kind of go all in and I think you know, do the apps. I did like a lunch date service. I did like Jewish speed dating one day, which that was also a very funny, terrible story, you know. Do the apps, I did like a lunch date service. I did like Jewish speed dating one day, which that was also a very funny, terrible story. You know, I did all the things. It's like I really was. You know, and I'm super interested in like matchmakers and things like that, because I love I'm.

Speaker 2: 33:12

I one of my goals is to like interview and talk to more matchmakers because I think that that's such an interesting concept. Like my friend, anne has this amazing intuition, but I feel like you really have to have intuition because when you're a matchmaker, your pool's only as good as the people that are in it. So if you're trying to just match up people cause they're in your pool, that's not as good as if you like I recently set somebody up because it was sort of a similar situation. They recently set somebody up because it was sort of a similar situation. They're both in New York and every time I see him, I think of her, which is like weird, and so I? I haven't. They haven't gone out yet but we'll see what happens.

Speaker 1: 33:45

Yeah, all right, before I let you go, heidi, the one question I always love to ask folks is what is your empty nest, or what is your life motto? And perhaps, coming out of this whole journey, what's a couple of word sentence that's like this is this defines?

Speaker 2: 34:04

my life in this moment. That's a. That's a tough, interesting question. So one of my favorite life model, life sayings I don't know why I couldn't think of the word is actually Comparison is the.

Speaker 2: 34:17

Thief of Joy, and I will say that my journey taught me that and I still am working on it.

Speaker 2: 34:27

It's not something, especially as an empty nester. You can see kids getting jobs and being successful while yours are struggling and you really can keep you up at night in not good ways and I am constantly reminding myself that comparison is the thief you know, is the thief of joy, and I tell my kids. And so social media makes that hard. And and then the other thing that kept me going is someone bought me like a little poster when I got divorced that said, when the caterpillar thought life was over, she became a butterfly and I still have like a little cutout of it that I keep next to my desk and I think it's just that's about hope and the whole reason that I am going around talking about this book. I mean, I have a very successful legal career, I love my day job, but I feel like we're in a time where spreading love and hope is just so important and if I can just give one person hope that they may find their person, then I'll feel really good about it.

Speaker 1: 35:28

That's a great way to finish the episode. Here she is, folks Heidi Friedman, helping people with hope of finding their true love, and, if you want it, the book Love Lessons 104 Dates and Stories that Led Me to True Love is available on amazoncom right now. Check it out, put it in the show notes for folks. Heidi, it's been an absolute pleasure having you on.

Speaker 2: 35:49

Thank you so much. This was so fun and I'm going to remember those four questions. I love those four questions. That's perfection. Tell your daughter she needs to listen to you?

Speaker 1: 36:00

I don't know.

Speaker 2: 36:01

You're planting seeds. You're planting seeds, they'll grow, I promise.