June 3, 2025 • 29 mins
LOVE LESSONS
Heidi B. Friedman, an environmental attorney and divorced mother of two, set out on a mission to find true love. Determined to understand the complexities of relationships, she immersed herself in research, embraced dating, and committed to doing whatever it took to find the right partner. Over a decade, she went on 104 dates (not with 104 different men!) and interviewed numerous couples, uncovering invaluable love lessons along the way. Written over 15 years, Love Lessons: 104 Dates and the Stories That Led Me to True Love chronicles Heidi’s journey—everything she learned, every challenge she faced, and ultimately, how she found lasting love with the man who is now her husband.
Heidi shares the invaluable lessons she’s learned to help women, men, and even young adults navigate their own journeys to true love. While there’s no official handbook for choosing the right life partner, her book comes remarkably close, offering wisdom, insights, and real-world guidance for anyone seeking a meaningful and lasting relationship.
Book: Love Lessons: 104 Dates and the Stories That Led Me to True Love
Follow HeidiHeidi Friedman|Love Lessons Author (@lovelessons104) • Instagram photos and videos
instagram.com
Heidi B. Friedman, an environmental attorney and divorced mother of two, set out on a mission to find true love. Determined to understand the complexities of relationships, she immersed herself in research, embraced dating, and committed to doing whatever it took to find the right partner. Over a decade, she went on 104 dates (not with 104 different men!) and interviewed numerous couples, uncovering invaluable love lessons along the way. Written over 15 years, Love Lessons: 104 Dates and the Stories That Led Me to True Love chronicles Heidi’s journey—everything she learned, every challenge she faced, and ultimately, how she found lasting love with the man who is now her husband.
Heidi shares the invaluable lessons she’s learned to help women, men, and even young adults navigate their own journeys to true love. While there’s no official handbook for choosing the right life partner, her book comes remarkably close, offering wisdom, insights, and real-world guidance for anyone seeking a meaningful and lasting relationship.
Book: Love Lessons: 104 Dates and the Stories That Led Me to True Love
Follow HeidiHeidi Friedman|Love Lessons Author (@lovelessons104) • Instagram photos and videos
instagram.com
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hi, I'm Wendy, and this is Divorce Doesn't Suck. I'm
talking all about the life you can live after divorce.
You'll hear regular people's stories about their divorces and how
they reinvented themselves and grew. You'll also get invaluable advice
from experts who serve in the divorce community. A little
about me. I'm a former TV producer and mom of two.
I got divorced in two thousand and eight when there
were really no outlets or platforms for me to turn to.
(00:22):
So I'm paying it forward and have created a platform
to help men and women learn that there absolutely is
a fresh, new and exciting life after divorce. Come with
me on this journey and paint your brand new blank
canvas of happily ever after divorce. This episode is brought
to in part by the Needle Kuda Law Firm Guidance
that Moves Lives Forward. Welcome to another episode of Divorce
(00:43):
Doesn't Suck. I'm Wendy Sloan, your host and my guest. Today,
after being single for almost ten years and surviving one
hundred and four dates, well not actually one hundred and
four people, but we'll get to that. My guest today
is living happily ever after. She is a successful partner
at a large law firm and just released her first book,
(01:04):
Love Lessons, one hundred and four Dates and the Stories
That Led Me to True Love. I have goosebums just
saying that. Welcome to my show, Heidi Friedman.
Speaker 2 (01:14):
Thanks, Wendy, It's so fun to be here. Can't wait
to chat with you.
Speaker 1 (01:17):
Oh, I'm so excited for this one hundred and four date,
but not actually one hundred and four, but I want
to know about that. But okay, big law firms specialized
in the area's environmental author of this book, And before
we dive all into that and your ten year journey
to finding your person, can you start before that, because
in between that so much building a law practice. As
(01:39):
a single mom, you got divorced. Can we back up
to that part of life and then we'll venture in
to the newest.
Speaker 2 (01:48):
Absolutely. So, I got divorced when my kids worth three
and five, and I was a true single mama. So
their dad ended up not having much of a role,
and I was privileged enough to have an a pair
at some point who became someone of my life, partner
(02:08):
and helping me raise the kids, and she's part of
my family. I'm a very much it takes a village
kind of person, and I really was trying to build
my law practice at the same time, so it was
a lot of put the kids to bed, work afterwards,
all of those things. And I'm so glad I did
because once the kids are out of the house, it's
(02:29):
absolutely lovely to be able to have a professional career
that I'm excited about and now I can put my
passion into my book as well. So those were not
fun times. I think I include a lot of journal
entries that I kept. I will tell you there were
lonely days and nights, and sometimes I felt like I
was not being a good mom or a good lawyer.
(02:51):
But I certainly did the best I can. Yeah, I
certainly did the best that I could during those times.
Speaker 1 (02:58):
It's not easy. It does, and I and I was
I am a single mom, and I was a single
mom raising them mostly by myself as well, So I
totally get that. But but kudos to you for having
that passion for your career too, and something for yourself
as well while raising the kids. So that's pretty amazing.
(03:18):
And then when did the tenuere so you were so
basically single. When did you start the journey on dating
and how did this come up to be a ten
year journey?
Speaker 2 (03:30):
Well, I was at the time hoping it was not
going to be a ten year journey. But I mean
to be honest, I you know, live in Cleveland. It's
a close knit community. I was the first person in
sort of my entire group of friends and things like
that to get divorced, and everyone and their mother literally
was fixing me up. And it wasn't thoughtful fix ups.
(03:50):
It was oh, he's divorced and she's divorced, let you know.
And so you'd leave these dates and you're like, is
this what best person thinks of me? Oh? No, and
it would just I remember after the fourth or fifth date,
I decided to start counting because I said, this is
going to be a journey and I'm just curious to
see where it goes. And I so I started it
(04:13):
pretty quickly after I was divorced, just to kind of
put myself out there. But that process itself was a
couple of years, so you know, it took a while,
and I started actually reconnecting with a friend that I
knew growing up who was also getting divorced, and you know,
that was kind of my first little fling and it
was fun. But then I went on to date about
(04:33):
fifty five people over ten years, and it was a
combination of fix ups and some people that I sort
of met organically but very few, and then some app
things and a lot of the dates were you know,
ten minutes or fifteen minutes, and thank god you had
small kids to go home too, So you know, it
wasn't until I was, I think, in a much different
(04:56):
place and had become a different person and so much
more confident that I was introduced to my now husband,
and so it was sort of right place, right time,
all of that, and it was the end of this
you know, very very long and wine do road.
Speaker 1 (05:13):
So what was so so it was a bunch of
it was a mix of people fixing you up, organically
meeting which is not easy when you're building a career
and you have small kids at home. It's like hard
to find time to get out there. And then the
apps and what was what was each of those journeys
Like what were the apps like? Like was that like
when you got the kids tucked into bed and you
had a minute to yourself and then you start like scrolling.
(05:35):
It's like, you know, you're scrolling on Instagram or TikTok, right.
Speaker 2 (05:39):
You know, it's funny because the apps back fifteen years
ago were so different than they were. It was basically
like eHarmony and Match dot Com and maybe a little Jday,
but you know, nothing really from there for me, and
it was I always I was, you know. I started
a podcast with my son actually called I Love You
More and we're talking about dating and how different the
(06:01):
apps are now and how younger kids used them as
much more of a way to meet people than we did.
And for me, it was kind of a way to
safely put myself out there. And I will say, through
Match dot Com I had two fairly I would call
situationships where I dated someone two different guys at two
(06:23):
different times for a number of months and saw them,
you know, sporadically. But there were two people that I
would have never met otherwise and they were most definitely
not my person. But it allowed me to put myself
out there. But my problem with the apps that I
encourage people to use them all the time when they
asked me, you know, how to do this journey because
(06:44):
it kind of puts you in a dating mindset and
allows you to do your own due diligence. Right. You
can email back and forth with someone, I can decide
he's completely wacko and then not go out with him,
or you know, do my own due diligence. But it
but at the end of the day, I think there's
a lot lack of authenticity around how we put ourselves
out there on the apps. So I don't think you
(07:04):
could start a relationship without being authentic. So that was
my experience on the apps. It was it was fine.
I had some good experience, they were growth experiences, and
then the fix ups were you know, interesting. They weren't
thoughtful for most for the most part, but I was
open to them, and I actually think that is the
(07:25):
number one best way to meet somebody. And when I
met my husband, it was actually through a friend at yoga,
So it was someone I hardly When I say friend,
I'm using that term extremely loosely. Now she's like my
sister by the time, she was like an acquaintance who
I practiced yoga x two for years in the front
row with the other type a people. So you know,
(07:46):
it wasn't like this unbelievable, like you're my best see
kind of thing. It was much more of expanding my circle.
And you know, I think that's how you get to
know people who you would not otherwise meet. And you
know that's how that happened for me.
Speaker 1 (08:02):
So what what what? So the awkward dates, the not's
so good ones, that everything in between, how did you
get out of them? What was? What did it leave
you feeling? Did you act? And when did you start
with the book? When did you start writing? You said
you started, you know, writing down how many dates you
went on, But when did all that begin?
Speaker 2 (08:20):
Sure? So to answer your first question, the awkward dates,
I really used my kids as an excuse constantly. And
so I would, you know, basically say oh my god,
my kids are calling, or you know, something happened at home,
and you know it was just I had to go.
I mean I really did have probably a handful of
(08:41):
more of ten or fifteen minutes, and I was outy,
but I did try to. I didn't try to for
the most part, commit to at least an hour or something.
And you know, see if maybe you know, the initial
awkwardness would go away. But and then I'd often have
friends saying, oh, just try one more time, go out
with them again. I know, he asked, and you know
I don't like wasting time, so I very much would
(09:04):
respond and say, you know, I don't think it's a connection,
but I wish you luck, and I'm I'm just pretty
truthful about that. But in the book, So what happened
with the book is I woke up and I was
turning forty. I mean, I didn't wake up and I
was turning forty, but I was turning forty. I had
a couple of years of dating under my belt. I'd
obviously been married, and it's probably pretty pathetic to admit,
(09:26):
but I decided I didn't know what true love looked like.
I really felt that I had not felt true love,
and so I decided to do research. I'm a super
analytical person. I like data. Data is everything to me.
And I started interviewing mostly women, but some men who
I felt like were in good marriages, and I asked
(09:47):
them a bunch of questions, how did you know? What
you know? What was it like? And I gathered all
this data, and at the time, I was traveling a
lot for work of a very national practice. I was
on airplanes a lot. Every time I would fly, I
would take out my notes and I would kind of
think about things, and I realized that the more people
I talked to, the same themes were emerging, and I
(10:10):
thought it was so interesting, and so I started writing
the first you know, one third of the book when
I was forty and with about these themes for my research,
and then I put it away. I think they were
in the back of my head as I move forward dating,
and then I found it a few years ago. I
was like, Wow, it would be so cool to think
about these themes in connection with my current relationship with
(10:32):
my now husband, and so I did it, and then
one thing led to another and I ended up, you know,
writing the book. But the initial part of the book
is you know, over fifteen years old.
Speaker 1 (10:42):
Actually, I was amazed when I read that. I was
amazed by that. I was like, oh my gosh, we're
going to take a very quick break with sponsor will
be right back with a commercial break. The book is
Love Lessons, one hundred and four Dates and the Stories
that led Me to true Love. I still want to
ask you more about the couple that you interviewed, and
then I want to ask you about will your person
(11:04):
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We're back with Heidi Friedman, author attorney, her new book
(12:30):
Love Lessons one hundred and four Dates and the Stories
that Led Me to True Love. I could say that
one hundred times because I love the title of that book. Okay,
the couples that you interviewed, you said there was a common,
something so common. Tell me because it's so funny, because
so much of you. I see me in because I
would go on a few dates way way way back then,
and I'd be like, oh yeah, sure, I'll go get
(12:51):
your son from football. Oh yeah, I've got to go.
I would like break away really quick if I and
like walk out like you. I don't want to waste
any time. And then I also so I just want
to break this in there, and I hope I can
do this because I've never done this on this podcast.
But I was listening to an interview that you did
and you were like, well what they said, what was
the song that reminded you of you? And I'm like,
(13:14):
holy moly. When I had my radio show, it was
one of my theme songs. So I'm just going to
play it really quick so hopefully it works. And I
thought this was funny. Ready, yes, coming.
Speaker 3 (13:44):
I could hear it a little bit, but yes, the
fight song Rachel Platten, that was one of my theme
songs during my radio show.
Speaker 1 (13:55):
I had changed it several times, but that was one
of them. And I was like, I so connected with
you on so many levels, and we would like playing.
Speaker 2 (14:02):
It at the top of our lungs. And if you
ask my kids, they like have saying it a hundred
times because it just gave me, I don't know, some
kind of outlet of okay, it's all going to be okay.
I don't know what it is. I love that song.
That's so funny, but I know, so that's why.
Speaker 1 (14:18):
And then just like you know, reading about you before
I even interviewed, I like, oh god, we have so
much in common. Okay, So the interview was what was
the theme? And by the way, I when I see couples,
I always say I'm not interviewing them, but I'm like,
what's your secret, what's the magic? What is it?
Speaker 2 (14:34):
So there was about ten themes, and I would say,
there's a couple that really stuck with me. And the
number one theme was that they took turns, basically caring
for each other and supporting each other. And my therapist
I read about this in the book, had this analogy
for me because I am a serial fixer and helper
(14:58):
and all of that, and you know, in a real
good relationship. Her analogy was it picture yourself in an ocean.
If you're going under, someone's pulling your up, and then
that person goes under and you pull them up, and
it's just a back and forth versus the same person
pulling up, you know, the serial puller upper or whatever
you want to call her. And a lot of these
(15:21):
people talked about the fact that they had hard times
and they took turns and it wasn't one sided, and
that was just so profound to me, I think. And
then another one was really the fact that it just
felt easy. It was not square peg in round hole.
(15:41):
It was authentic, it was natural from the beginning. It
felt like home. I mean, that's how some people described it,
and those really stuck with me in a really good way.
They really showed me that it does have to feel right.
You have to listen into your gut, you have to
(16:01):
have a true partnership, and you know there are There
are several others, but those are probably the two that
were most impactful to me.
Speaker 1 (16:09):
I love that when you said it feels like home,
and I guess you'll know it. You know you'll know it.
So meeting will Yes, you're forever and you joined your
families together. Tell us, tell us how that went, and
tell us about the first date, and tell us how
when the moment that you knew and all that.
Speaker 2 (16:31):
Of course, so it was a fix up. I definitely
would not have gone out with. And this is another
big thing for me. Do not have too many rules.
He was ten years old. That he is ten years
older than me, and at first I was like, that's
too old. And he had also not been completely divorced,
and I had this role that they had to be
(16:51):
like at least a year out of the divorce, but
he had a very extended divorce for a variety of reasons.
And so we went on a first date. We met
actually at it called stagrant Instagram falls. It's this suburb
cute little place. Had a drink. Drink turned into dinner,
dinner turned into another drink. You know, Like we ended
up having quite a long date and we connected, I
(17:12):
mean unbelievably. It was literally like I had known him forever,
but he had not been a date on a date
in twenty seven years, and so I was definitely like
seven years. I mean right, he was married for twenty
four and then he was with his ex wife for
three years before that, so it was for maybe twenty
four years. It was some insane amount of time. He
(17:34):
had never really text before. Text was sort of just
coming into you know, our lives then as well. And
so I even kissed him good night, like I was
being a little more aggressive than usual, which is.
Speaker 1 (17:44):
Not like me.
Speaker 2 (17:46):
But you know, I wouldn't say I knew that night.
I knew it was different that night. And we were
not supposed to see each other for another week, and
we ended up seeing each other sooner, and I would
say by the third time I saw him, absolutely new
and it was you know, challenging. You know, we I
had two kids, he has two kids, and you know,
(18:07):
bringing your kids together is something I had. Despite the
fact that I had dated fifty some people, no one
had met my kids. And I feel very proud of
that because I felt like my kids were not dating
and my son at the time was dying for, like,
you know, a guy in his life that was a
father figure, and I knew it would not work out
well if I broke up with somebody and so, but
(18:30):
I pretty quickly introduced Will, so that could tell you
where my confidence level was. And so we just took
our time with the kids and brought them together a
little slowly, and like it's funny when I look back now,
because we are truly, like, like incredibly blended. I mean,
one of my boys and one of will boys are
like besties and talk every day, and you know, the
(18:53):
whole thing, and our family vacations are my everything. I
love when the four of us, the six of us
together with the four kids, you know, it's fantastic. So
it's one of those beautiful stories for sure. And I
truly believe that kids can't have enough people that love them,
and so my kids have had the gift of Will,
(19:13):
and I hope his kids feel like they have the
gift of me. And we I treasure my relationships with
my bonus kids. Incredibly, they have added so much to
my life. So it's a really beautiful story. That is
a beautiful story.
Speaker 1 (19:27):
I'm so happy for you and I and I loved
everything that you said about the whole way like you knew,
you knew, and I like you. I didn't introduce my
kids to anyone. I just for for some reason that
was like, I have no regrets. That was my safe
place for them. And and you did it. You did
it when the timing was right for you. So all
of this life today, life in Cleveland with your husband,
(19:51):
will your mixed rescue Felix, your four kids, your two
could your two and your two combined life today? Would
you looking back all of that happened, which is exactly
what my show is. This is what happened to me.
This is how I got here, and this is how
I'm living my best life. It's you. You are. This book,
your book, Love Lessons, one hundred and four Dates and
(20:12):
the stories that led me to true love. There's so
much in this book besides just about your dates as
well and just about the couples that you internefinitely like that.
There's so much to be you know so much in
this book. What about life Heidi today.
Speaker 2 (20:26):
Heidi today is beyond grateful. I literally like We'll always
make some I me because sometimes I'll just stare at
him and I'm just like, I can't believe I have
you in my life. And he had breast cancer a
couple of years ago. Meant that's my PSA and men
can get breast cancer too, And it was like the
(20:47):
scariest time of my life. It was worse than anything
I'd been through. And he was, you know, a warrior,
and you know, we knock on wood every day, and
you know, we just you know, I pray and I
hope that we have another thirty years together. But we
love being empty nesters. We are certainly working on parenting
our adult children. Some are adulting better than others, and
(21:10):
it's a journey, especially in the world today and the challenges.
But I truly feel like if I have him by
my side, I can do anything. There is nowhere I
rather be than with him. We have built a wonderful community,
We have fabulous friends and all of that, and I'm
super inspired. Like my goal right now with my book
is to spread love and hope. And I think we're
(21:32):
living in a time where we lack love and hope,
and that's what Zach and I are trying to do
with our podcast, I Love You More Too, is just
to talk about it doesn't matter if you're twenty two
or fifty two or seventy two. I think you can
find love and you can have hope, and you have
to do it your way. And so that's my journey now.
And I feel so grateful. And sometimes I think you say,
(21:53):
you know, you have to look back to see where
you are. And I read those journal entries and by
the way, like my kids and well read those and
made them so sad, and because I don't think they
ever saw me in that light, and which I said
is perfect because I don't want you to have known that.
But I read those and I'm just like, wow, it
(22:13):
makes me appreciate my life so much more in order
to be able to see how far I've come. So
it's really a gift. I'm so grateful.
Speaker 1 (22:22):
Yeah, if you hadn't if you hadn't gotten a divorce,
and if you hadn't been a single mom, you know,
building your law practice and going on all those dates,
will might not be It might not be will, and
you might not be living your life. Your book is
full of wisdom. It's authenticity, authentic, it's so insightful. It's
a journey for anyone who's looking for love. And I
(22:43):
agree with you. We should spread more love out there
every single day and we can do this. I mean,
I love what you said. You said you look at
him and you're like so like, can't believe this is
your life. It wouldn't be your life if you hadn't
traveled all those to all those places. This is what
was meant to be for you.
Speaker 2 (23:01):
I think so. I said in our wedding as part
of our rows that my journey, albeit bumpy and windy,
led me to you. So I would go it over
and over again if I had to, because this was
my destination and every step was worth it just to
have him in my life. So I know people think
we're so cheesy and over the top, and would be.
It's where we came from. We appreciate each other so
(23:24):
much more. But it was the bumpy, windy, horrible date.
All of it was worth it.
Speaker 1 (23:31):
Oh absolutely, So what do you want to tell people
out there besides everything that you've already said. Let's talk
more a little bit more about your book. When people
are reading your book, what do you want them to
get from it?
Speaker 2 (23:43):
You know, we have eleven love lessons at the end,
and I really that's a combination of my dating, my relationship,
and my research. And I think that if you're on
a journey, whether it's to connect more with your current
significant other or to find somebody knew for the first
time or for the second time, I hope that those
(24:05):
lessons that I learned will help you on your journey.
And I think the one thing that surprised me more
than anything else about the book, I did think it
would relate to people like us. You write people who
had been divorced, had moved on. That was kind of
who I was targeting. I have had so many women
who read it who are in happy marriages, and they
(24:27):
said that they thought it was so wonderful to realize
what they had, the themes that related to them, the
love lessons that made sense to them and almost made
them want to like double down and refocus on their
significant other. And that just made me elated, Like I
was like, Wow, that's so meaningful to me. And I've
gotten emails from people that I don't you know, don't
(24:48):
know to my Gmail and the book and you know,
saying how impactful and meaningful it was, and that just
makes me so happy. So, I mean, my number one
thing is you have to have an open heart, you
have to have an open mind, and you have to
put yourself out there. I mean, no one is going
to come find you on your couch unless it's like
the Ups guy or Amazon guy or whatever. If you
(25:09):
really want to, you know, add someone to your life,
you have to have this open vibe too. So I
hope those lessons are helpful, and I love hearing from people.
I want people to follow me at Love Lessons one
O four. I hope you'll listen to my podcast with
Zach I Love You More, which is on Spotify and
(25:30):
we're working on getting it on Apple. It's a little bit,
it's been a little bit of a thing.
Speaker 1 (25:35):
Well you'll be on Apple podcast for this interview.
Speaker 2 (25:38):
That's awesome. That's awesome. So and you know, I'm just
I love talking about it. I love speaking about it.
I love just spreading love. I mean, it's it sounds toesy.
I'm a super romantic, but I feel like everyone should
have a will. Everyone deserves this in their life, a
true partner. I mean I have since i've him, I
(26:00):
have never had to do anything alone. And I'm an
independent person. Like don't get me wrong, I am like
misindependent woman. You know. RBG is my idol. But man,
having somebody to support you as everything.
Speaker 1 (26:13):
Oh, I love this. This interview made me so happy.
Reading your book made me so happy. Here made me
so happy. And all that you're doing for everybody out
there makes me happy because you know, because we all,
you know, anyone who's listening has been through some kind
of journey. So this gives everybody like hope and you
know that's what we need, and we need more of that.
(26:34):
We need more love and more hope in this world
and more happily.
Speaker 2 (26:38):
Ever after one hundred percent, I say to my kids too,
if I just sat when things didn't work out on
these days and I just sat there and cried on
my bed all the time, and I did cry in
my bed, don't let me like, Yeah, I certainly did.
But if I didn't get up, you know and put
my big girl on dependent on and go out on
the act date, I mean, it wouldn't have happened. And
so you just got to no matter what you're going through,
(27:00):
you got to keep on keeping on and fake it
till you make it a little bit. And you really
just have to have hope. And I think we all
need hope right now. And I think that it just
just don't get caught in the you know, soccer, whatever
you want to call it, because that's a bad place
to be. And I think sometimes it's just switching your mindset.
Speaker 1 (27:25):
So much good information and you did it all as
a single mom, big law, big partner in a big
law firm. I mean that's incredible in itself as well.
And then can you imagine when you look back and
you're like, oh, I was writing down like I was
on my fifth date, I was on my sixth day,
and then starting you know, you had these stories back
there for twelve years or so whatever, right, and then
(27:47):
who would have known that this was going to happen exactly?
We need more of this happiness love Lessons one hundred
and four Dates and the stories that led me to
true love. Heidi Friedman, such a great book, Wisdom, Insight,
follow this Journey was just everyone should read it and
everyone should have this journey for themselves. Thank you so
much for being here.
Speaker 2 (28:06):
Thank you, Wendy. So fun to talk to you. I
love that our stories are so similar.
Speaker 1 (28:12):
I also believe there's another book in you.
Speaker 2 (28:15):
There might be another book in me. I would love
to write another book. If there's anybody who wants to
pick me up, I'd be super grateful.
Speaker 1 (28:22):
I feel like there's another book in you. Thank you
so much, Heidi.
Speaker 2 (28:25):
Thanks Wendy, Take care.
Speaker 1 (28:27):
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(29:13):
two O three five five seven nine five zero zero
Hi, I'm Wendy, and this is Divorce Doesn't Suck. I'm
talking all about the life you can live after divorce.
You'll hear regular people's stories about their divorces and how
they reinvented themselves and grew. You'll also get invaluable advice
from experts who serve in the divorce community. A little
about me. I'm a former TV producer and mom of two.
I got divorced in two thousand and eight when there
were really no outlets or platforms for me to turn to.
(00:22):
So I'm paying it forward and have created a platform
to help men and women learn that there absolutely is
a fresh, new and exciting life after divorce. Come with
me on this journey and paint your brand new blank
canvas of happily ever after divorce. This episode is brought
to in part by the Needle Kuda Law Firm Guidance
that Moves Lives Forward. Welcome to another episode of Divorce
(00:43):
Doesn't Suck. I'm Wendy Sloan, your host and my guest. Today,
after being single for almost ten years and surviving one
hundred and four dates, well not actually one hundred and
four people, but we'll get to that. My guest today
is living happily ever after. She is a successful partner
at a large law firm and just released her first book,
(01:04):
Love Lessons, one hundred and four Dates and the Stories
That Led Me to True Love. I have goosebums just
saying that. Welcome to my show, Heidi Friedman.
Speaker 2 (01:14):
Thanks, Wendy, It's so fun to be here. Can't wait
to chat with you.
Speaker 1 (01:17):
Oh, I'm so excited for this one hundred and four date,
but not actually one hundred and four, but I want
to know about that. But okay, big law firms specialized
in the area's environmental author of this book, And before
we dive all into that and your ten year journey
to finding your person, can you start before that, because
in between that so much building a law practice. As
(01:39):
a single mom, you got divorced. Can we back up
to that part of life and then we'll venture in
to the newest.
Speaker 2 (01:48):
Absolutely. So, I got divorced when my kids worth three
and five, and I was a true single mama. So
their dad ended up not having much of a role,
and I was privileged enough to have an a pair
at some point who became someone of my life, partner
(02:08):
and helping me raise the kids, and she's part of
my family. I'm a very much it takes a village
kind of person, and I really was trying to build
my law practice at the same time, so it was
a lot of put the kids to bed, work afterwards,
all of those things. And I'm so glad I did
because once the kids are out of the house, it's
(02:29):
absolutely lovely to be able to have a professional career
that I'm excited about and now I can put my
passion into my book as well. So those were not
fun times. I think I include a lot of journal
entries that I kept. I will tell you there were
lonely days and nights, and sometimes I felt like I
was not being a good mom or a good lawyer.
(02:51):
But I certainly did the best I can. Yeah, I
certainly did the best that I could during those times.
Speaker 1 (02:58):
It's not easy. It does, and I and I was
I am a single mom, and I was a single
mom raising them mostly by myself as well, So I
totally get that. But but kudos to you for having
that passion for your career too, and something for yourself
as well while raising the kids. So that's pretty amazing.
(03:18):
And then when did the tenuere so you were so
basically single. When did you start the journey on dating
and how did this come up to be a ten
year journey?
Speaker 2 (03:30):
Well, I was at the time hoping it was not
going to be a ten year journey. But I mean
to be honest, I you know, live in Cleveland. It's
a close knit community. I was the first person in
sort of my entire group of friends and things like
that to get divorced, and everyone and their mother literally
was fixing me up. And it wasn't thoughtful fix ups.
(03:50):
It was oh, he's divorced and she's divorced, let you know.
And so you'd leave these dates and you're like, is
this what best person thinks of me? Oh? No, and
it would just I remember after the fourth or fifth date,
I decided to start counting because I said, this is
going to be a journey and I'm just curious to
see where it goes. And I so I started it
(04:13):
pretty quickly after I was divorced, just to kind of
put myself out there. But that process itself was a
couple of years, so you know, it took a while,
and I started actually reconnecting with a friend that I
knew growing up who was also getting divorced, and you know,
that was kind of my first little fling and it
was fun. But then I went on to date about
(04:33):
fifty five people over ten years, and it was a
combination of fix ups and some people that I sort
of met organically but very few, and then some app
things and a lot of the dates were you know,
ten minutes or fifteen minutes, and thank god you had
small kids to go home too, So you know, it
wasn't until I was, I think, in a much different
(04:56):
place and had become a different person and so much
more confident that I was introduced to my now husband,
and so it was sort of right place, right time,
all of that, and it was the end of this
you know, very very long and wine do road.
Speaker 1 (05:13):
So what was so so it was a bunch of
it was a mix of people fixing you up, organically
meeting which is not easy when you're building a career
and you have small kids at home. It's like hard
to find time to get out there. And then the
apps and what was what was each of those journeys
Like what were the apps like? Like was that like
when you got the kids tucked into bed and you
had a minute to yourself and then you start like scrolling.
(05:35):
It's like, you know, you're scrolling on Instagram or TikTok, right.
Speaker 2 (05:39):
You know, it's funny because the apps back fifteen years
ago were so different than they were. It was basically
like eHarmony and Match dot Com and maybe a little Jday,
but you know, nothing really from there for me, and
it was I always I was, you know. I started
a podcast with my son actually called I Love You
More and we're talking about dating and how different the
(06:01):
apps are now and how younger kids used them as
much more of a way to meet people than we did.
And for me, it was kind of a way to
safely put myself out there. And I will say, through
Match dot Com I had two fairly I would call
situationships where I dated someone two different guys at two
(06:23):
different times for a number of months and saw them,
you know, sporadically. But there were two people that I
would have never met otherwise and they were most definitely
not my person. But it allowed me to put myself
out there. But my problem with the apps that I
encourage people to use them all the time when they
asked me, you know, how to do this journey because
(06:44):
it kind of puts you in a dating mindset and
allows you to do your own due diligence. Right. You
can email back and forth with someone, I can decide
he's completely wacko and then not go out with him,
or you know, do my own due diligence. But it
but at the end of the day, I think there's
a lot lack of authenticity around how we put ourselves
out there on the apps. So I don't think you
(07:04):
could start a relationship without being authentic. So that was
my experience on the apps. It was it was fine.
I had some good experience, they were growth experiences, and
then the fix ups were you know, interesting. They weren't
thoughtful for most for the most part, but I was
open to them, and I actually think that is the
(07:25):
number one best way to meet somebody. And when I
met my husband, it was actually through a friend at yoga,
So it was someone I hardly When I say friend,
I'm using that term extremely loosely. Now she's like my
sister by the time, she was like an acquaintance who
I practiced yoga x two for years in the front
row with the other type a people. So you know,
(07:46):
it wasn't like this unbelievable, like you're my best see
kind of thing. It was much more of expanding my circle.
And you know, I think that's how you get to
know people who you would not otherwise meet. And you
know that's how that happened for me.
Speaker 1 (08:02):
So what what what? So the awkward dates, the not's
so good ones, that everything in between, how did you
get out of them? What was? What did it leave
you feeling? Did you act? And when did you start
with the book? When did you start writing? You said
you started, you know, writing down how many dates you
went on, But when did all that begin?
Speaker 2 (08:20):
Sure? So to answer your first question, the awkward dates,
I really used my kids as an excuse constantly. And
so I would, you know, basically say oh my god,
my kids are calling, or you know, something happened at home,
and you know it was just I had to go.
I mean I really did have probably a handful of
(08:41):
more of ten or fifteen minutes, and I was outy,
but I did try to. I didn't try to for
the most part, commit to at least an hour or something.
And you know, see if maybe you know, the initial
awkwardness would go away. But and then I'd often have
friends saying, oh, just try one more time, go out
with them again. I know, he asked, and you know
I don't like wasting time, so I very much would
(09:04):
respond and say, you know, I don't think it's a connection,
but I wish you luck, and I'm I'm just pretty
truthful about that. But in the book, So what happened
with the book is I woke up and I was
turning forty. I mean, I didn't wake up and I
was turning forty, but I was turning forty. I had
a couple of years of dating under my belt. I'd
obviously been married, and it's probably pretty pathetic to admit,
(09:26):
but I decided I didn't know what true love looked like.
I really felt that I had not felt true love,
and so I decided to do research. I'm a super
analytical person. I like data. Data is everything to me.
And I started interviewing mostly women, but some men who
I felt like were in good marriages, and I asked
(09:47):
them a bunch of questions, how did you know? What
you know? What was it like? And I gathered all
this data, and at the time, I was traveling a
lot for work of a very national practice. I was
on airplanes a lot. Every time I would fly, I
would take out my notes and I would kind of
think about things, and I realized that the more people
I talked to, the same themes were emerging, and I
(10:10):
thought it was so interesting, and so I started writing
the first you know, one third of the book when
I was forty and with about these themes for my research,
and then I put it away. I think they were
in the back of my head as I move forward dating,
and then I found it a few years ago. I
was like, Wow, it would be so cool to think
about these themes in connection with my current relationship with
(10:32):
my now husband, and so I did it, and then
one thing led to another and I ended up, you know,
writing the book. But the initial part of the book
is you know, over fifteen years old.
Speaker 1 (10:42):
Actually, I was amazed when I read that. I was
amazed by that. I was like, oh my gosh, we're
going to take a very quick break with sponsor will
be right back with a commercial break. The book is
Love Lessons, one hundred and four Dates and the Stories
that led Me to true Love. I still want to
ask you more about the couple that you interviewed, and
then I want to ask you about will your person
(11:04):
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We're back with Heidi Friedman, author attorney, her new book
(12:30):
Love Lessons one hundred and four Dates and the Stories
that Led Me to True Love. I could say that
one hundred times because I love the title of that book. Okay,
the couples that you interviewed, you said there was a common,
something so common. Tell me because it's so funny, because
so much of you. I see me in because I
would go on a few dates way way way back then,
and I'd be like, oh yeah, sure, I'll go get
(12:51):
your son from football. Oh yeah, I've got to go.
I would like break away really quick if I and
like walk out like you. I don't want to waste
any time. And then I also so I just want
to break this in there, and I hope I can
do this because I've never done this on this podcast.
But I was listening to an interview that you did
and you were like, well what they said, what was
the song that reminded you of you? And I'm like,
(13:14):
holy moly. When I had my radio show, it was
one of my theme songs. So I'm just going to
play it really quick so hopefully it works. And I
thought this was funny. Ready, yes, coming.
Speaker 3 (13:44):
I could hear it a little bit, but yes, the
fight song Rachel Platten, that was one of my theme
songs during my radio show.
Speaker 1 (13:55):
I had changed it several times, but that was one
of them. And I was like, I so connected with
you on so many levels, and we would like playing.
Speaker 2 (14:02):
It at the top of our lungs. And if you
ask my kids, they like have saying it a hundred
times because it just gave me, I don't know, some
kind of outlet of okay, it's all going to be okay.
I don't know what it is. I love that song.
That's so funny, but I know, so that's why.
Speaker 1 (14:18):
And then just like you know, reading about you before
I even interviewed, I like, oh god, we have so
much in common. Okay, So the interview was what was
the theme? And by the way, I when I see couples,
I always say I'm not interviewing them, but I'm like,
what's your secret, what's the magic? What is it?
Speaker 2 (14:34):
So there was about ten themes, and I would say,
there's a couple that really stuck with me. And the
number one theme was that they took turns, basically caring
for each other and supporting each other. And my therapist
I read about this in the book, had this analogy
for me because I am a serial fixer and helper
(14:58):
and all of that, and you know, in a real
good relationship. Her analogy was it picture yourself in an ocean.
If you're going under, someone's pulling your up, and then
that person goes under and you pull them up, and
it's just a back and forth versus the same person
pulling up, you know, the serial puller upper or whatever
you want to call her. And a lot of these
(15:21):
people talked about the fact that they had hard times
and they took turns and it wasn't one sided, and
that was just so profound to me, I think. And
then another one was really the fact that it just
felt easy. It was not square peg in round hole.
(15:41):
It was authentic, it was natural from the beginning. It
felt like home. I mean, that's how some people described it,
and those really stuck with me in a really good way.
They really showed me that it does have to feel right.
You have to listen into your gut, you have to
(16:01):
have a true partnership, and you know there are There
are several others, but those are probably the two that
were most impactful to me.
Speaker 1 (16:09):
I love that when you said it feels like home,
and I guess you'll know it. You know you'll know it.
So meeting will Yes, you're forever and you joined your
families together. Tell us, tell us how that went, and
tell us about the first date, and tell us how
when the moment that you knew and all that.
Speaker 2 (16:31):
Of course, so it was a fix up. I definitely
would not have gone out with. And this is another
big thing for me. Do not have too many rules.
He was ten years old. That he is ten years
older than me, and at first I was like, that's
too old. And he had also not been completely divorced,
and I had this role that they had to be
(16:51):
like at least a year out of the divorce, but
he had a very extended divorce for a variety of reasons.
And so we went on a first date. We met
actually at it called stagrant Instagram falls. It's this suburb
cute little place. Had a drink. Drink turned into dinner,
dinner turned into another drink. You know, Like we ended
up having quite a long date and we connected, I
(17:12):
mean unbelievably. It was literally like I had known him forever,
but he had not been a date on a date
in twenty seven years, and so I was definitely like
seven years. I mean right, he was married for twenty
four and then he was with his ex wife for
three years before that, so it was for maybe twenty
four years. It was some insane amount of time. He
(17:34):
had never really text before. Text was sort of just
coming into you know, our lives then as well. And
so I even kissed him good night, like I was
being a little more aggressive than usual, which is.
Speaker 1 (17:44):
Not like me.
Speaker 2 (17:46):
But you know, I wouldn't say I knew that night.
I knew it was different that night. And we were
not supposed to see each other for another week, and
we ended up seeing each other sooner, and I would
say by the third time I saw him, absolutely new
and it was you know, challenging. You know, we I
had two kids, he has two kids, and you know,
(18:07):
bringing your kids together is something I had. Despite the
fact that I had dated fifty some people, no one
had met my kids. And I feel very proud of
that because I felt like my kids were not dating
and my son at the time was dying for, like,
you know, a guy in his life that was a
father figure, and I knew it would not work out
well if I broke up with somebody and so, but
(18:30):
I pretty quickly introduced Will, so that could tell you
where my confidence level was. And so we just took
our time with the kids and brought them together a
little slowly, and like it's funny when I look back now,
because we are truly, like, like incredibly blended. I mean,
one of my boys and one of will boys are
like besties and talk every day, and you know, the
(18:53):
whole thing, and our family vacations are my everything. I
love when the four of us, the six of us
together with the four kids, you know, it's fantastic. So
it's one of those beautiful stories for sure. And I
truly believe that kids can't have enough people that love them,
and so my kids have had the gift of Will,
(19:13):
and I hope his kids feel like they have the
gift of me. And we I treasure my relationships with
my bonus kids. Incredibly, they have added so much to
my life. So it's a really beautiful story. That is
a beautiful story.
Speaker 1 (19:27):
I'm so happy for you and I and I loved
everything that you said about the whole way like you knew,
you knew, and I like you. I didn't introduce my
kids to anyone. I just for for some reason that
was like, I have no regrets. That was my safe
place for them. And and you did it. You did
it when the timing was right for you. So all
of this life today, life in Cleveland with your husband,
(19:51):
will your mixed rescue Felix, your four kids, your two
could your two and your two combined life today? Would
you looking back all of that happened, which is exactly
what my show is. This is what happened to me.
This is how I got here, and this is how
I'm living my best life. It's you. You are. This book,
your book, Love Lessons, one hundred and four Dates and
(20:12):
the stories that led me to true love. There's so
much in this book besides just about your dates as
well and just about the couples that you internefinitely like that.
There's so much to be you know so much in
this book. What about life Heidi today.
Speaker 2 (20:26):
Heidi today is beyond grateful. I literally like We'll always
make some I me because sometimes I'll just stare at
him and I'm just like, I can't believe I have
you in my life. And he had breast cancer a
couple of years ago. Meant that's my PSA and men
can get breast cancer too, And it was like the
(20:47):
scariest time of my life. It was worse than anything
I'd been through. And he was, you know, a warrior,
and you know, we knock on wood every day, and
you know, we just you know, I pray and I
hope that we have another thirty years together. But we
love being empty nesters. We are certainly working on parenting
our adult children. Some are adulting better than others, and
(21:10):
it's a journey, especially in the world today and the challenges.
But I truly feel like if I have him by
my side, I can do anything. There is nowhere I
rather be than with him. We have built a wonderful community,
We have fabulous friends and all of that, and I'm
super inspired. Like my goal right now with my book
is to spread love and hope. And I think we're
(21:32):
living in a time where we lack love and hope,
and that's what Zach and I are trying to do
with our podcast, I Love You More Too, is just
to talk about it doesn't matter if you're twenty two
or fifty two or seventy two. I think you can
find love and you can have hope, and you have
to do it your way. And so that's my journey now.
And I feel so grateful. And sometimes I think you say,
(21:53):
you know, you have to look back to see where
you are. And I read those journal entries and by
the way, like my kids and well read those and
made them so sad, and because I don't think they
ever saw me in that light, and which I said
is perfect because I don't want you to have known that.
But I read those and I'm just like, wow, it
(22:13):
makes me appreciate my life so much more in order
to be able to see how far I've come. So
it's really a gift. I'm so grateful.
Speaker 1 (22:22):
Yeah, if you hadn't if you hadn't gotten a divorce,
and if you hadn't been a single mom, you know,
building your law practice and going on all those dates,
will might not be It might not be will, and
you might not be living your life. Your book is
full of wisdom. It's authenticity, authentic, it's so insightful. It's
a journey for anyone who's looking for love. And I
(22:43):
agree with you. We should spread more love out there
every single day and we can do this. I mean,
I love what you said. You said you look at
him and you're like so like, can't believe this is
your life. It wouldn't be your life if you hadn't
traveled all those to all those places. This is what
was meant to be for you.
Speaker 2 (23:01):
I think so. I said in our wedding as part
of our rows that my journey, albeit bumpy and windy,
led me to you. So I would go it over
and over again if I had to, because this was
my destination and every step was worth it just to
have him in my life. So I know people think
we're so cheesy and over the top, and would be.
It's where we came from. We appreciate each other so
(23:24):
much more. But it was the bumpy, windy, horrible date.
All of it was worth it.
Speaker 1 (23:31):
Oh absolutely, So what do you want to tell people
out there besides everything that you've already said. Let's talk
more a little bit more about your book. When people
are reading your book, what do you want them to
get from it?
Speaker 2 (23:43):
You know, we have eleven love lessons at the end,
and I really that's a combination of my dating, my relationship,
and my research. And I think that if you're on
a journey, whether it's to connect more with your current
significant other or to find somebody knew for the first
time or for the second time, I hope that those
(24:05):
lessons that I learned will help you on your journey.
And I think the one thing that surprised me more
than anything else about the book, I did think it
would relate to people like us. You write people who
had been divorced, had moved on. That was kind of
who I was targeting. I have had so many women
who read it who are in happy marriages, and they
(24:27):
said that they thought it was so wonderful to realize
what they had, the themes that related to them, the
love lessons that made sense to them and almost made
them want to like double down and refocus on their
significant other. And that just made me elated, Like I
was like, Wow, that's so meaningful to me. And I've
gotten emails from people that I don't you know, don't
(24:48):
know to my Gmail and the book and you know,
saying how impactful and meaningful it was, and that just
makes me so happy. So, I mean, my number one
thing is you have to have an open heart, you
have to have an open mind, and you have to
put yourself out there. I mean, no one is going
to come find you on your couch unless it's like
the Ups guy or Amazon guy or whatever. If you
(25:09):
really want to, you know, add someone to your life,
you have to have this open vibe too. So I
hope those lessons are helpful, and I love hearing from people.
I want people to follow me at Love Lessons one
O four. I hope you'll listen to my podcast with
Zach I Love You More, which is on Spotify and
(25:30):
we're working on getting it on Apple. It's a little bit,
it's been a little bit of a thing.
Speaker 1 (25:35):
Well you'll be on Apple podcast for this interview.
Speaker 2 (25:38):
That's awesome. That's awesome. So and you know, I'm just
I love talking about it. I love speaking about it.
I love just spreading love. I mean, it's it sounds toesy.
I'm a super romantic, but I feel like everyone should
have a will. Everyone deserves this in their life, a
true partner. I mean I have since i've him, I
(26:00):
have never had to do anything alone. And I'm an
independent person. Like don't get me wrong, I am like
misindependent woman. You know. RBG is my idol. But man,
having somebody to support you as everything.
Speaker 1 (26:13):
Oh, I love this. This interview made me so happy.
Reading your book made me so happy. Here made me
so happy. And all that you're doing for everybody out
there makes me happy because you know, because we all,
you know, anyone who's listening has been through some kind
of journey. So this gives everybody like hope and you
know that's what we need, and we need more of that.
(26:34):
We need more love and more hope in this world
and more happily.
Speaker 2 (26:38):
Ever after one hundred percent, I say to my kids too,
if I just sat when things didn't work out on
these days and I just sat there and cried on
my bed all the time, and I did cry in
my bed, don't let me like, Yeah, I certainly did.
But if I didn't get up, you know and put
my big girl on dependent on and go out on
the act date, I mean, it wouldn't have happened. And
so you just got to no matter what you're going through,
(27:00):
you got to keep on keeping on and fake it
till you make it a little bit. And you really
just have to have hope. And I think we all
need hope right now. And I think that it just
just don't get caught in the you know, soccer, whatever
you want to call it, because that's a bad place
to be. And I think sometimes it's just switching your mindset.
Speaker 1 (27:25):
So much good information and you did it all as
a single mom, big law, big partner in a big
law firm. I mean that's incredible in itself as well.
And then can you imagine when you look back and
you're like, oh, I was writing down like I was
on my fifth date, I was on my sixth day,
and then starting you know, you had these stories back
there for twelve years or so whatever, right, and then
(27:47):
who would have known that this was going to happen exactly?
We need more of this happiness love Lessons one hundred
and four Dates and the stories that led me to
true love. Heidi Friedman, such a great book, Wisdom, Insight,
follow this Journey was just everyone should read it and
everyone should have this journey for themselves. Thank you so
much for being here.
Speaker 2 (28:06):
Thank you, Wendy. So fun to talk to you. I
love that our stories are so similar.
Speaker 1 (28:12):
I also believe there's another book in you.
Speaker 2 (28:15):
There might be another book in me. I would love
to write another book. If there's anybody who wants to
pick me up, I'd be super grateful.
Speaker 1 (28:22):
I feel like there's another book in you. Thank you
so much, Heidi.
Speaker 2 (28:25):
Thanks Wendy, Take care.
Speaker 1 (28:27):
Nito Kuda Divorce and Family Laws attorneys have guided Connecticut
and New York families through complex divorce actions, contested child custody,
and alimony disputes for over thirty years. Their Connecticut and
New York attorneys have extensive experience in family matters involving
substance abuse, domestic violence, mental illness, and many other X
factors that can complicate a divorce. Their attorneys a deptly
(28:50):
managed privacy and reputation concerns inherit to public divorce proceedings
and the related exposure for their ultra high net worth clients.
Find your new path forward, define your post divorce family,
and secure an enforceable agreement to protect your future with
Needle Cuda Act. Now put the strength of their team
behind you. Visit them at Needlecuda dot com or call
(29:13):
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