June 28, 2025 • 36 mins
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)
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
If you find yourself divorced or single and wondering
whether or not you canrediscover love in midlife, then
today you're in for a treat.
On today's episode, I'm joinedby Heidi Friedman, a divorced
mother of two who found herselfin the middle of midlife
wondering hey, does true loveeven exist?
So, determined to find theanswer, she immersed herself in
(00:23):
research and dating 104different dates over a 10-year
span, and let me tell you thatturned into a book.
She's the author of LoveLessons 104 Dates and Stories
that Led Her to True Love, andso we're going to jump into her
journey today and find out allthe things you ever wanted to
know about finding true love inmidlife.
Heidi, welcome to thisEmptiness Life.
Speaker 2 (00:45):
Thank you so much.
I am so excited to be here andto join you and your listeners
to chat about love lessons.
Speaker 1 (00:51):
So we were talking a little bit beforehand about
there are different componentsto love life as the kids grow.
But I wouldn't be a good hostif I didn't ask this first
question.
You said 104 dates in 10 years.
Seriously, 104 dates.
Speaker 2 (01:06):
Seriously 104 days, not 104 guys, it was about 55
guys.
Speaker 1 (01:11):
People will be wondering that question 104
different people.
How does that even possible?
Speaker 2 (01:14):
Yes, it is the number one question I get.
So there was three or four guyswho I dated for some period of
time.
My youngest son taught me theterm situationship, which is,
like you know, not definitelynot equivalent to a relationship
, which none of them really were, but I did count those dates.
Speaker 1 (01:34):
Yeah, situationships that's, I think, a new term for
folks especially you know, ourage like Gen Xers and people who
are in midlife and maybe emptynested.
I know some of the youngercoaches out there who deal in
relationships.
All they talk about issituations.
Speaker 2 (01:48):
Right, exactly, exactly.
So I'm learning as I go.
Speaker 1 (01:52):
Well, hopefully not now.
Now you're remarried, rightyeah, so hopefully that kind of
life is done.
Speaker 2 (01:56):
We just had our 10-year anniversary so all is
good.
Speaker 1 (02:00):
Tell me about the book itself.
It's a really intriguing titlefor me and for my listeners, who
it's like, hey, they findthemselves 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 tocollege and then I've talked
about it on the show before Graydivorce happens and people are
kind of like blindsided and theyfind themselves wondering ooh,
(02:25):
is this it so?
Is it?
Clearly it's not about yourjourney.
Speaker 2 (02:29):
It's not.
It's not.
And I just had a friend gothrough literally exactly as you
described and she read the bookand she was really said.
I gave her hope which is allI'm trying to do spread some
love and give some hope.
So the book actually was bornaround my 40th birthday, because
I had woken up on my 40thbirthday and I had been divorced
(02:51):
for several years and haddecided okay, I don't know why,
but I don't think I have everbeen truly in love which you can
judge me.
I was married, but it was adifferent situation, not that
sort of partnership, deep truelove, that where you're totally
(03:12):
madly in love with someone.
And so I started interviewingfriends who I thought had what I
saw, as you know, idyllicmarriages, or at least they like
, really loved each other, youknow.
And my questions were how didyou know it was your person, you
know.
And my questions were how didyou know it was your person?
How does it keep?
How does he or she keep youhappy?
What is the best part of yourrelationship?
All of the things.
I never talked to a coupletogether.
(03:33):
I always talked to in, like thehusband and wife individually,
if I talked to both of them,because I only spoke to people
who I had pretty significantrelationships with, because I
was really looking for peoplethat I thought had figured it
out.
And so I'm an attorney by dayand I was traveling all over the
country at the time doingdepositions and on planes.
(03:56):
I would look at my notes frommy meetings and I realized after
some time that it was the samethemes were popping up over and
over again and I so I wroteabout eight chapters and with
some of those themes, and then Iparked it because I had started
to got to the point, actually,that I kept hearing the same
(04:17):
things over and over and I sortof was like, Okay, well, I
figured it out.
So I now I know what kind ofthese themes are and I continued
to date and then I actuallyforgot about the book.
I met my husband in 2013.
And then I had found the book,maybe about three or four years
(04:37):
ago, and I was like, wow, it'dbe really interesting to think
about my current relationship,how it applies to these themes,
think more about my dates andjust my journey.
And I honestly wrote the book1000% for our four kids we have.
I have two kids and two bonustwo kids that I've birthed and
two bonus children, all of whichare adulting at different
(05:00):
levels, from ages 22 to almost29 now, but I have seen some of
them in what I would call notthe best choice relationships
and I really wanted them tolearn from my mistakes and not
settle.
So that was how the book wasborn and really the reason why I
ended up writing it.
Speaker 1 (05:20):
I love that so much For people who are listening.
We talked about finding love inmidlife and they're like, oh,
but that was you know, you werein your late 30s as opposed to
being in your 50s.
But I feel like everythingwe're going to talk about today
applies no matter where you are,in what stage of life.
Speaker 2 (05:35):
you could, you know, connect with me at the end and I
have gotten emails from superrandom people, even married
couples, who said that they usedit as a tool to kind of
re-monitor and re-evaluate theircurrent relationship, and they
(05:56):
found it super helpful.
And I've definitely.
I've done a bunch of booksignings and I've met a lot of,
especially women who are inmidlife or even a little bit
beyond.
I just had a 70-year-old reachout to me who's dating again for
the first time.
So there's hope for all of usand it's just a matter of
putting yourself out there invarious different ways and I
(06:16):
think everyone can find loveagain if they really want to.
Speaker 1 (06:19):
You mentioned your son, talked about situationships
, but younger folks talk aboutred flag, green flags and yellow
flags and their relationship.
Have you learned about thosetwo?
And then did you find those inyour journey of these 104 dates?
Speaker 2 (06:33):
There was only the red flag concept back in my day.
These other flags are sort ofnew to me.
I definitely had a lot of redflag dates.
I think the number one questionI get is you know what was your
worst, craziest date?
And there were so many thatit's actually hard to pick.
I think what happened is when Istarted my journey, I was not
(06:56):
very confident personally but Iwas confident professionally and
I kind of grew over this10-year process into someone who
is much more confident, muchmore able to tune up my gut and
find the red flags and thereforelook for the waving green flag
at the end of the day which aresometimes hard to find.
Speaker 1 (07:17):
That is true.
I would imagine as part of yourjourney, you worked a lot on
yourself.
First, is that fair?
Worked a lot on yourself first,is that fair?
Speaker 2 (07:23):
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 unpackand I learned a lot through the
process, and I think I truly dobelieve that each relationship,
even if it doesn't work out,teaches you something that you
can take with you on to the nextrelationship, and you just sort
(07:46):
of have to figure out what itis, and sometimes, when you're
knee deep in it, you can't seeit, but when you get some space
from it, you look backwards.
Then I think it comes to lifeand tells you what that lesson
is, that you can carry on as youkind of move towards what maybe
and hopefully would be yoursort of true love or your person
.
Speaker 1 (08:04):
Let's say, you work on yourself a little bit and
then how do you, or how doessomeone, date with confidence?
What does that even look like?
Speaker 2 (08:12):
You know it's hard.
I will be honest with you.
First of all, I think you haveto have an open heart and be
ready to date.
I did a book thing last weekand I had someone come up and
ask a question and she's stilltrying to get out of an old
relationship but also doing allthese things and I basically
said until that chapter isclosed you're not going to have
(08:34):
this open heart and open vibe.
That until that chapter isclosed you're not going to have
this open heart and open vibe.
And I actually, as much as Ialso hate the apps, I love the
apps because I think it's a safeway to put yourself out there,
as long as you have lowexpectations.
My 22 year old will tell you theapps are just you make him
crazy and he has a love-haterelationship with them and I
think those kids that age have adifferent dating philosophy.
(08:57):
But I think for older folks inour middle age and above that,
it allows you to safely you cando due diligence.
You can Google people, look atsocial media, make sure they're
not serial killers or bankruptor whatever you want to check,
and you can email back and forthuntil you get comfortable and
then you just go with like makemaybe I'm making a new friend.
(09:18):
This is not going to be thelove of my life, but it just
gives you practice.
Like I always say, would you gointo your dream job interview
without doing prep work and prepinterviews?
And so I look a little bit atonline dating and people haven't
met their significant other, soI'm not poo pooing it if it
happens, but I think if you gointo it more as a training type
(09:38):
thing, it works.
And then I also think you justhave to tell everyone you know
and I don't mean like yourlittle circle of friends,
because that's your circle youhave to grow that bigger and
wider, bigger and wider.
I'm a huge hot yoga fan and itkept me sane through being a
(10:00):
single mom and a divorce andstuff and I'm in the front row
always because I'm a type A haveto stare at the wall to like be
focused kind of person.
And I was next to the samethree people all the time on the
weekends and we became friendlyand rushing ahead to the end of
the punchline.
One of those people who Ihardly knew and basically took a
couple of years to even sayhello to, fixed me up with my
(10:22):
husband, who she didn't evenknow that well, but she worked
with him and just thought of meevery time she was with him and
she has wonderful intuition andshe definitely did a better job
fixing up than many people.
I had some bad fix ups but itwas about, you know, telling
people outside your circle, likethrough running club or yoga
(10:42):
club or pickleball or whateverpeople do these days.
Speaker 1 (10:45):
I love that.
So like from hot mess to hotyoga 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 awhile of being single and being
a single mom, I'm a superindependent person.
Anyways, I've always been ableto support myself.
I was one of the lucky people.
When you know, the choice todivorce was mine.
I was able to support myselfand my children, so it was much
(11:19):
easier, and I have extensivesympathy for women who are not
in that same situation and Ihelp and talk to those women
quite, quite often.
You can imagine, after so manyyears you kind of develop this
lifestyle and independence thatI almost thought I'm never going
to be able to fit somebody intothis equation anymore because I
(11:41):
got so used to uncomfortablekind of being alone.
I had definitely decided that Iwill be alone before I be with
the wrong person, even though Ikept trying.
So I think, like figuring outhow to integrate someone into my
life although Will made it veryeasy.
He's my husband and then ofcourse, one of the things to
think about is at the time hehad two boys who he was still
(12:04):
caring for and the primaryperson for, and we had to
integrate these kids and thattransition was really hard.
We were much slower with thatthan we were introducing him to
my kids, although in my 10 yearsof dating he was the only
introducing him to my kids,although he I.
In my 10 years of dating he wasthe only person I introduced my
kids to.
So I was not.
I'm a huge believer in it's nota play date.
(12:24):
I think I say in the book, andat 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 toughtransition and I would never
give up our now like extended,beautiful little combined family
(12:47):
.
Speaker 1 (12:47):
But yeah, for those people who may be going through
that, let's dig into that alittle bit more.
The work piece of finding truelove when it is a blended family
you know it's really, it issensitive, it's hard.
Speaker 2 (12:59):
Someone told me it might have even been the kids
therapist that it on averagetakes seven years for a blended
family to feel like a realfamily.
I think we were overachieversnot 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,
(13:20):
like literally talk all everyday, but they're also like both
obsessed with basketball and youknow certain family guy and
certain things that they're veryinterested in.
But we were super careful, likewhen we came together
physically into the same house,which was about a year after we
were together physically intothe same house, which was about
a year after we were togetherand a year before we got married
.
We made sure each kid had hisor her own space with a bathroom
(13:44):
and a bedroom so that no onewas on top of each other.
We tried to treat everybodyequal.
It was a unique situation forus because we're both the
primary parent for the childrenand so we had all the kids with
us all of the time.
So I think in a lot ofrelationships you have time as a
couple or back and forth, andso we didn't have that.
We went.
(14:05):
I went from being a mom of twoto, you know, being a bonus mom
to two others who like and atthis point I mean my step sons
are my everything.
I can't even imagine them notin my life, but I think you do
have to give them time.
It took one of the boys longerthan the other one to kind of
embrace me, and I think you justneed to push, especially if
(14:26):
there is another parent in thepicture, that I'm not here to
replace that parent, I'm just.
My true philosophy is you cannever have enough people that
love you, and especiallynowadays.
So I kind of feel like the morepeople that love you the better
.
And so, you know, just tryingto get that point across.
And eventually you know we gotthere, and now I feel like we
(14:49):
were all in Mexico forThanksgiving and I was like just
looking around our table,thinking like I just love this
family that we built which issomething that's really special.
Speaker 1 (14:57):
I love how it came together, and that might not
happen for everybody, so alittle disclaimer for people who
are going through this right itdoesn't always work this way,
but you also have to work at tomake it work.
Speaker 2 (15:09):
A hundred percent.
There was again lots oftherapists involved and you know
some some, you know mess upsI'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 Italked to a lot of women about.
(15:31):
I do think if you have adultchildren, like truly you know,
if I met Will now and everyone'sout of the house, I actually
think as much as you wanteveryone to come together.
It's harder, actually, becauseour kids growing up in the same
house, even if it was only forfive or seven years, made a huge
difference and I think itbecomes a little bit less
important to be completelyintegrated as you get a little
(15:52):
bit older and your kids areolder.
It's lovely and hopefully yourkids want you to be happy and
welcome whoever your newsignificant other is, but I do
think at a certain point itbecomes less relevant.
Speaker 1 (16:02):
Yeah, for sure, and a little bit, probably more
ingrained into like, oh, they'rereally a part of my life
because I'm an adult and I'vegot this going on over here,
right, what's one thing youlearned 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 makesure this was the right choice,
(16:36):
even though I knew in my gutthat it was.
And he did all this testing.
He was actually an excellenttherapist, 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 notsure I know what you're looking
for in your life, this truepartner.
I'm not sure you'll ever letanyone in enough to be able to,
(16:57):
like, take care of you, likeyou're saying, and that just
stuck with me.
I mean, it was so many yearsago and I it's, it's the most
beautiful.
We take care of each other.
There's, you know, my analogyin the book where, like, one of
the themes is that really strongcouples take care of each other
(17:17):
.
And, like, the analogy is whenthere's waves like, like, if
someone goes under, someonepulls up, and you can't always
be the puller upper, you have totake turns pulling each other
up, because if not, you knowyou're going to either be
exhausted or drown, basically.
So I just we have thiswonderful balance of supporting
and pulling each other up.
I give up like free control tohim, because I trust him so
(17:38):
inherently, and so that wasprobably my biggest revelation
that I was capable of and what arevelation.
Speaker 1 (17:43):
That was to be like thinking perhaps maybe you could
never fully give of yourself tosomeone to take care of you, to
be all the way like 180 degreeturn to say, oh my goodness,
yeah, it is amazing to havesomeone care for you in the way
that you deserve to be cared for.
Speaker 2 (17:59):
Totally, totally.
I'm always sort of thecaretaker, so it's such a nice
feeling to have that, and sothat 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 knowthat 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 dayback in the day was sort of like
matchcom, eharmony and like Jday.
But that J day was justterrible.
As a Jewish woman I was like,oh God, this I'm just.
If this is all that's out therehere, we're in trouble.
(18:36):
But and I found this guy onMatch and we had been emailing
and it seemed fine.
We were meeting at a bar for adrink.
I always tried to like make adate you know short, like not a
first date, like not a wholedinner, not like you know some
kind of you know short thing,whether it's coffee or a drink
or whatever.
(18:59):
It was easier at the time for meto have like some alcohol as I
was continuing to try to movepast this.
But I show up, he doesn't lookanything like his picture.
Like, literally, he had hair inhis picture.
He was completely bald, he waswearing some random turtleneck,
something I don't know, that'sall I remember.
But we were there for fiveminutes and he pulls out what's
called a cease and desist order,not, and that he had gotten it
(19:20):
from Pepsi because or Coke orsomething like that, because he
was selling stuff out of hisgarage and so he wanted me to
look at it as a lawyer and givehim legal advice.
And this is the time whereyou're like, oh my god, thank
God I have young children and Iwas like, oh my god, my
daughter's playing and I was, Ithink I was in and out of there
(19:41):
in eight minutes and likerunning to my car, it was just.
It was like, you know, just oneof those things, that.
But that went so badly and partof it was just he wanted like
some expertise rather than hadany interest in me, but just
generally.
And then he texted me and askedme 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 arewondering out, there is like you
have found true love.
Have you?
In the course of your researchor talking to other people?
Is it like?
Have you found folks doing thesame thing in midlife?
Like finding?
Speaker 2 (20:21):
their person, absolutely.
I have a couple of friends whoare on a second marriage, some
of who I interviewed the book,some of who I have not, and they
have definitely found theirperson, who they say was more of
their person than in the firstmarriage.
Because I also feel like, Imean, who I am at 45 is very
different than who I am at 28 orwhatever, and that's why I'm
(20:44):
also telling my kids to like,take your time, you do not have
to get married by the timeyou're 30.
Like you know, let's figure outwho you are and what you want
and and all the things.
So but but yeah, I mean, and Iwill say, the vast majority of
people that I interviewed forthe book the first time, I think
only one of them's gottendivorced since I interviewed
(21:05):
them, and those are some likethere's some serious longevity
in those marriages, but I do,I've sort of become like I think
when you're, like the firstperson divorced and I'm a lawyer
, anyways, I talked to a lot ofwomen who get divorced, so they
might be 30, 40, 50, 70.
I talked to someone 70 last week.
You know, it just depends, butI help them.
(21:25):
Try to understand.
You're at the bottom of thishill and you're going to get
over it and it's so beautiful onthe other side and all of the
things.
But you also want to get hopethat they're going to be able to
find love again, if that'ssomething that they're going to
be able to find love again, ifthat's something that they are
interested in, and so I thinkI'm a symbol of that for a lot
of people, which I reallyappreciate, because I always say
everyone needs a will, which ismy husband's name, and they
(21:48):
should all have a will in theirlife.
Speaker 1 (21:49):
Everybody should have a will.
Wait, not that type of will,this type of will.
This kind of will exactlyThroughout this journey, other
than finding will what was adefining moment for you.
Speaker 2 (22:03):
I think that I originally, right when I got
divorced, I started datingsomebody and it was symbolic of
some of my bad choices.
He turned out to have adrinking problem and it was
somebody that I think I did meethim online.
Actually, I only dated like twopeople that I had met online,
(22:25):
but I had.
I met him online and he was alawyer and we definitely clicked
.
There was like chemistry, itwas like one of those things.
But I found myself overlookingthese bright red flags.
I found myself overlookingthese bright red flags and, like
, I even found out later that hehad told me he was divorced but
he was really only separated,and so, you know, I was.
(22:47):
I was strong enough to like endthat and walk away pretty
freaking quickly, like comparedto before, but I definitely felt
that was a defining moment.
I'm not going to just findsomebody, even if there's
chemistry there, if the otherpieces of the puzzle are not
there for me, and I know what Ineed now and I need to be
careful to not go down that badroad again, and so that was
(23:11):
really a defining moment.
Speaker 1 (23:13):
That was probably like a year into, maybe two,
into being divorced, and I waslike, okay, like a year into,
maybe two, into being divorced,and I was like, okay, yeah, so
where my, where my coach braingoes for my listeners is you?
You needed to work on yourselffirst before you could figure
out what you want and you justhop 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 overthe 10 years I took lots of
breaks from dating.
There was many times where I'mlike I'm not dating anybody for
six months, I'm just focusing onme and my kids.
And I had busy times at workwhen I was traveling a lot and
all of that, and I kind of tookbreaks from the process.
(23:49):
And I would say the otherdefining moments were me.
For example, my oldest was BobMitzvah, 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 withme with my kids anyways, but
even without my kids like towork thing, this it was like too
stressful to me and I never wasreally in a relationship where
like it had reached the level of, okay, we can do this.
And so like showing up aloneall the time and like being the
odd person out really made mekind of assess my life but also
(24:23):
realize like, okay, I'm on myown best date and I can do this.
And I had lots of hystericaldating stories to share a
cocktail hour.
So I was very entertaining andyou know, I just I found that
every time I did it it got alittle bit easier.
Speaker 1 (24:38):
You just said a nugget in there which I want
people to like go back in hereis I was my own best date, and I
think that's how you become thebest version of yourself.
For other people is to becomeyour own best date, and then you
can figure out how other peoplefit into that Exactly.
Speaker 2 (24:53):
Exactly I really I wanted to be.
I did feel like when I met Willthat 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 thebook is he makes me a better
person.
Like he's such a good personand he's expanded me culturally
and like with arts and all kindsof stuff that I feel like you
(25:17):
know makes me a better person.
He was so encouraging to writethis book or whatever it is that
I want to do in my life.
He very much supports me and Isee him always doing well and
doing good and all of that andit 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 notethat I wrote for my daughter.
I was watching a movie, right,all the good things come from
movies.
It was about finding the rightperson and there were four
questions to ask Is he kind oris she kind?
Can you tell him everything inyour heart?
Does he help you become thebest version of yourself?
(25:52):
And then the final one is canyou imagine him as the father of
your kids?
But that plays out too, ifyou're a blended family, like a
supporter of your kids, let'ssay.
Speaker 2 (26:03):
But I thought those are easy.
Four questions, those arefabulous.
Speaker 1 (26:06):
And so my daughter's 25.
My son's 27.
But I was like oh, I'm writingthose down and tucking those
away for later.
I don't think she listens tothis.
Oh, she's not going to hearthose 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 abouthow many of my friends you know
we all sort of have adult.
I have tons of friends who havethe kids the same age as our
kids and so many of them havebought the book for their kids
and I've heard from so many ofthe kids and because I think
they hear me my kids talk abouthow they've learned so much from
the process and things likethat.
A friend of mine uses this term,noah's Ark theory, which is
kind of the thought that in ourworld everyone feels like you
(26:48):
have to be matched up in apaired up, and so you kind of
have this inclination like it'sbetter to have someone in my
life rather than to be alone.
And what I'm trying to tell mykids is, first of all, you're
not ready to be a partner untilyou're your best version of
yourself.
Like for Valentine's Day thisyear, I sent them all $100, all
four of them and I said takeyourself out to do something
(27:10):
yourself and focus on yourselffor at least an hour, because
you are your best Valentine andyou're not going to be able to
be a Valentine to someone elseuntil you do that.
And so they're all excitedabout the money, of course, but
still I think they got themessage.
And so the goal is like for thekids to understand that they
don't need to fall into this.
I need, need a partner, I needa date, I need whatever.
(27:33):
They need to focus onthemselves, you know, put your
mirror on yourself, and then wecan 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 mydaughter's brain too.
It's like you don't needsomebody else to complete you
right yourself first.
Then you find somebody whocompliments you doesn't complete
you compliment oh, I like thattoo.
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 themrewrite it exactly.
Vacation exactly together mywife 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 forthe beach so she has some noreen
.
I'm like listen to this podcastepisode first and then I've got
something for you Perfect.
Speaker 2 (28:18):
Perfect and it's been fun.
I started a podcast with my22-year-old and he's done
podcasts before, but we'recalling it I Love you More.
It's available on Spotify andApple and we're talking about
all things dating, relationshipsand love generationally and I
will be honest that it's broughtme more joy than anything I've
(28:41):
ever done in my life just havingthese super in-depth
conversations with Zach.
But at the same time, I havelearned so much and just how you
know the way these kids willapproach people on Tinder or
Hinge but not walk up to them ata bar, I mean, and it's just
how swiping's almost can be agame sometimes and it's just
(29:05):
this.
It's just a very.
I mean I've learned a millionthings, but it's just been this
interesting journey and I amlearning a lot and I think that
modern love and modern datingfor our kids looks different and
I actually am like promoting tomy four like let's date in the
wild people, like let's deletethe apps and let's put yourself
(29:25):
out there and do things becauseyou know maybe meeting people
will actually be good for you,like in real time.
Speaker 1 (29:33):
Exactly.
Forget the swipe left and swiperight.
How about you know?
Be right in front of somebodyinstead?
I love that.
So I do have some youngerlisteners who listen to the show
.
I'm just curious what are themain differences that you and
your son talk about on that?
Speaker 2 (29:50):
show so far.
We just started it and he'sgraduating next week, so it's a
little bit on hold for a minute.
But you know, the maindifference is literally, I would
definitely say, the technologyand I would just say the number
of apps and how they'reformatted.
And we just talked a lot, youknow, like what you have to put
(30:12):
in and how people are trying tocultivate a vibe rather than
authenticity trying to cultivatea vibe rather than authenticity
and we've talked a lot aboutthe fact that being authentic is
really the foundation for astrong relationship.
So, in my head, meetingsomebody online like that, when
you're not being your true self,is very challenging from like a
(30:33):
foundational standpoint, andyou know he definitely agreed
with that.
We talked a lot about fix-ups, Ithink last episode and that and
you know they're not remotelyinto that whole thing, I mean.
But he's 22 and even my 25, 27,they've never really been fixed
up and and I was, so I said Ithink I asked him last time
(30:55):
would you let me fix you up?
And he's like you know, maybe Ido think that they might want to
trust like people in theirlives, to maybe fix them up at
work or in other places and seehow that goes.
I do sense, though, that thereis this kind of burgeoning
(31:17):
joining and like turning awayfrom the apps, and I think that,
hopefully, leaving college willwill change that, at least for
like my baby, and hopefully forothers, and so you know, it's
also I think there's a lot oflearning that they're trying to
do like.
Zach was basically explaininglike I'm 22, I'm not the best
(31:37):
version of myself.
He's a super self aware kid,and he was saying that I know
I'm not ready to be in arelationship, I know I've made
wrong choices, and so I feellike, even if I dated somebody
now, it wouldn't be my personforever, and so I might, when
I'm ready for that, I mightapproach 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 peoplethrough your circle of friends,
which is small, or at a barright, right.
The kids are like so true likeeven 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 bestsolution yeah, it's part and
parcel of everything, a littlebit of both.
They're like a really goodrecipe the apps, meeting people
going out there and just talkingto anybody, those types of
things.
So that's, I think that's howyou 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 kindof go all in and I think you
know, do the apps.
I did like a lunch date service.
I did like Jewish speed datingone day, which that was also a
very funny, terrible story, youknow.
Do the apps, I did like a lunchdate service.
I did like Jewish speed datingone day, which that was also a
very funny, terrible story.
(33:02):
You know, I did all the things.
It's like I really was.
You know, and I'm superinterested in like matchmakers
and things like that, because Ilove I'm.
I one of my goals is to likeinterview and talk to more
matchmakers because I think thatthat's such an interesting
concept.
Like my friend, anne has thisamazing intuition, but I feel
like you really have to haveintuition because when you're a
(33:24):
matchmaker, your pool's only asgood as the people that are in
it.
So if you're trying to justmatch up people cause they're in
your pool, that's not as goodas if you like I recently set
somebody up because it was sortof a similar situation.
They recently set somebody upbecause it was sort of a similar
situation.
They're both in New York andevery time I see him, I think of
her, which is like weird, andso I?
I haven't.
They haven't gone out yet butwe'll see what happens.
Speaker 1 (33:45):
Yeah, all right, before I let you go, heidi, the
one question I always love toask folks is what is your empty
nest, or what is your life motto?
And perhaps, coming out of thiswhole journey, what's a couple
of word sentence that's likethis is this defines?
Speaker 2 (34:04):
my life in this moment.
That's a.
That's a tough, interestingquestion.
So one of my favorite lifemodel, life sayings I don't know
why I couldn't think of theword is actually Comparison is
the.
Thief of Joy, and I will saythat my journey taught me that
(34:26):
and I still am working on it.
It's not something, especiallyas an empty nester.
You can see kids getting jobsand being successful while yours
are struggling and you reallycan keep you up at night in not
good ways and I am constantlyreminding myself that comparison
is the thief you know, is thethief of joy, and I tell my kids
(34:47):
.
And so social media makes thathard.
And and then the other thingthat kept me going is someone
bought me like a little posterwhen I got divorced that said,
when the caterpillar thoughtlife was over, she became a
butterfly and I still have likea little cutout of it that I
keep next to my desk and I thinkit's just that's about hope and
(35:08):
the whole reason that I amgoing around talking about this
book.
I mean, I have a verysuccessful legal career, I love
my day job, but I feel likewe're in a time where spreading
love and hope is just soimportant and if I can just give
one person hope that they mayfind 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 HeidiFriedman, helping people with
hope of finding their true love,and, if you want it, the book
Love Lessons 104 Dates andStories that Led Me to True Love
is available on amazoncom rightnow.
Check it out, put it in theshow notes for folks.
Heidi, it's been an absolutepleasure having you on.
Speaker 2 (35:49):
Thank you so much.
This was so fun and I'm goingto remember those four questions
.
I love those four questions.
That's perfection.
Tell your daughter she needs tolisten to you?
Speaker 1 (36:00):
I don't know.
Speaker 2 (36:01):
You're planting seeds .
You're planting seeds, they'llgrow, I promise.
If you find yourself divorced or single and wondering
whether or not you canrediscover love in midlife, then
today you're in for a treat.
On today's episode, I'm joinedby Heidi Friedman, a divorced
mother of two who found herselfin the middle of midlife
wondering hey, does true loveeven exist?
So, determined to find theanswer, she immersed herself in
(00:23):
research and dating 104different dates over a 10-year
span, and let me tell you thatturned into a book.
She's the author of LoveLessons 104 Dates and Stories
that Led Her to True Love, andso we're going to jump into her
journey today and find out allthe things you ever wanted to
know about finding true love inmidlife.
Heidi, welcome to thisEmptiness Life.
Speaker 2 (00:45):
Thank you so much.
I am so excited to be here andto join you and your listeners
to chat about love lessons.
Speaker 1 (00:51):
So we were talking a little bit beforehand about
there are different componentsto love life as the kids grow.
But I wouldn't be a good hostif I didn't ask this first
question.
You said 104 dates in 10 years.
Seriously, 104 dates.
Speaker 2 (01:06):
Seriously 104 days, not 104 guys, it was about 55
guys.
Speaker 1 (01:11):
People will be wondering that question 104
different people.
How does that even possible?
Speaker 2 (01:14):
Yes, it is the number one question I get.
So there was three or four guyswho I dated for some period of
time.
My youngest son taught me theterm situationship, which is,
like you know, not definitelynot equivalent to a relationship
, which none of them really were, but I did count those dates.
Speaker 1 (01:34):
Yeah, situationships that's, I think, a new term for
folks especially you know, ourage like Gen Xers and people who
are in midlife and maybe emptynested.
I know some of the youngercoaches out there who deal in
relationships.
All they talk about issituations.
Speaker 2 (01:48):
Right, exactly, exactly.
So I'm learning as I go.
Speaker 1 (01:52):
Well, hopefully not now.
Now you're remarried, rightyeah, so hopefully that kind of
life is done.
Speaker 2 (01:56):
We just had our 10-year anniversary so all is
good.
Speaker 1 (02:00):
Tell me about the book itself.
It's a really intriguing titlefor me and for my listeners, who
it's like, hey, they findthemselves 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 tocollege and then I've talked
about it on the show before Graydivorce happens and people are
kind of like blindsided and theyfind themselves wondering ooh,
(02:25):
is this it so?
Is it?
Clearly it's not about yourjourney.
Speaker 2 (02:29):
It's not.
It's not.
And I just had a friend gothrough literally exactly as you
described and she read the bookand she was really said.
I gave her hope which is allI'm trying to do spread some
love and give some hope.
So the book actually was bornaround my 40th birthday, because
I had woken up on my 40thbirthday and I had been divorced
(02:51):
for several years and haddecided okay, I don't know why,
but I don't think I have everbeen truly in love which you can
judge me.
I was married, but it was adifferent situation, not that
sort of partnership, deep truelove, that where you're totally
(03:12):
madly in love with someone.
And so I started interviewingfriends who I thought had what I
saw, as you know, idyllicmarriages, or at least they like
, really loved each other, youknow.
And my questions were how didyou know it was your person, you
know.
And my questions were how didyou know it was your person?
How does it keep?
How does he or she keep youhappy?
What is the best part of yourrelationship?
All of the things.
I never talked to a coupletogether.
(03:33):
I always talked to in, like thehusband and wife individually,
if I talked to both of them,because I only spoke to people
who I had pretty significantrelationships with, because I
was really looking for peoplethat I thought had figured it
out.
And so I'm an attorney by dayand I was traveling all over the
country at the time doingdepositions and on planes.
(03:56):
I would look at my notes frommy meetings and I realized after
some time that it was the samethemes were popping up over and
over again and I so I wroteabout eight chapters and with
some of those themes, and then Iparked it because I had started
to got to the point, actually,that I kept hearing the same
(04:17):
things over and over and I sortof was like, Okay, well, I
figured it out.
So I now I know what kind ofthese themes are and I continued
to date and then I actuallyforgot about the book.
I met my husband in 2013.
And then I had found the book,maybe about three or four years
(04:37):
ago, and I was like, wow, it'dbe really interesting to think
about my current relationship,how it applies to these themes,
think more about my dates andjust my journey.
And I honestly wrote the book1000% for our four kids we have.
I have two kids and two bonustwo kids that I've birthed and
two bonus children, all of whichare adulting at different
(05:00):
levels, from ages 22 to almost29 now, but I have seen some of
them in what I would call notthe best choice relationships
and I really wanted them tolearn from my mistakes and not
settle.
So that was how the book wasborn and really the reason why I
ended up writing it.
Speaker 1 (05:20):
I love that so much For people who are listening.
We talked about finding love inmidlife and they're like, oh,
but that was you know, you werein your late 30s as opposed to
being in your 50s.
But I feel like everythingwe're going to talk about today
applies no matter where you are,in what stage of life.
Speaker 2 (05:35):
you could, you know, connect with me at the end and I
have gotten emails from superrandom people, even married
couples, who said that they usedit as a tool to kind of
re-monitor and re-evaluate theircurrent relationship, and they
(05:56):
found it super helpful.
And I've definitely.
I've done a bunch of booksignings and I've met a lot of,
especially women who are inmidlife or even a little bit
beyond.
I just had a 70-year-old reachout to me who's dating again for
the first time.
So there's hope for all of usand it's just a matter of
putting yourself out there invarious different ways and I
(06:16):
think everyone can find loveagain if they really want to.
Speaker 1 (06:19):
You mentioned your son, talked about situationships
, but younger folks talk aboutred flag, green flags and yellow
flags and their relationship.
Have you learned about thosetwo?
And then did you find those inyour journey of these 104 dates?
Speaker 2 (06:33):
There was only the red flag concept back in my day.
These other flags are sort ofnew to me.
I definitely had a lot of redflag dates.
I think the number one questionI get is you know what was your
worst, craziest date?
And there were so many thatit's actually hard to pick.
I think what happened is when Istarted my journey, I was not
(06:56):
very confident personally but Iwas confident professionally and
I kind of grew over this10-year process into someone who
is much more confident, muchmore able to tune up my gut and
find the red flags and thereforelook for the waving green flag
at the end of the day which aresometimes hard to find.
Speaker 1 (07:17):
That is true.
I would imagine as part of yourjourney, you worked a lot on
yourself.
First, is that fair?
Worked a lot on yourself first,is that fair?
Speaker 2 (07:23):
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 unpackand I learned a lot through the
process, and I think I truly dobelieve that each relationship,
even if it doesn't work out,teaches you something that you
can take with you on to the nextrelationship, and you just sort
(07:46):
of have to figure out what itis, and sometimes, when you're
knee deep in it, you can't seeit, but when you get some space
from it, you look backwards.
Then I think it comes to lifeand tells you what that lesson
is, that you can carry on as youkind of move towards what maybe
and hopefully would be yoursort of true love or your person
.
Speaker 1 (08:04):
Let's say, you work on yourself a little bit and
then how do you, or how doessomeone, date with confidence?
What does that even look like?
Speaker 2 (08:12):
You know it's hard.
I will be honest with you.
First of all, I think you haveto have an open heart and be
ready to date.
I did a book thing last weekand I had someone come up and
ask a question and she's stilltrying to get out of an old
relationship but also doing allthese things and I basically
said until that chapter isclosed you're not going to have
(08:34):
this open heart and open vibe.
That until that chapter isclosed you're not going to have
this open heart and open vibe.
And I actually, as much as Ialso hate the apps, I love the
apps because I think it's a safeway to put yourself out there,
as long as you have lowexpectations.
My 22 year old will tell you theapps are just you make him
crazy and he has a love-haterelationship with them and I
think those kids that age have adifferent dating philosophy.
(08:57):
But I think for older folks inour middle age and above that,
it allows you to safely you cando due diligence.
You can Google people, look atsocial media, make sure they're
not serial killers or bankruptor whatever you want to check,
and you can email back and forthuntil you get comfortable and
then you just go with like makemaybe I'm making a new friend.
(09:18):
This is not going to be thelove of my life, but it just
gives you practice.
Like I always say, would you gointo your dream job interview
without doing prep work and prepinterviews?
And so I look a little bit atonline dating and people haven't
met their significant other, soI'm not poo pooing it if it
happens, but I think if you gointo it more as a training type
(09:38):
thing, it works.
And then I also think you justhave to tell everyone you know
and I don't mean like yourlittle circle of friends,
because that's your circle youhave to grow that bigger and
wider, bigger and wider.
I'm a huge hot yoga fan and itkept me sane through being a
(10:00):
single mom and a divorce andstuff and I'm in the front row
always because I'm a type A haveto stare at the wall to like be
focused kind of person.
And I was next to the samethree people all the time on the
weekends and we became friendlyand rushing ahead to the end of
the punchline.
One of those people who Ihardly knew and basically took a
couple of years to even sayhello to, fixed me up with my
(10:22):
husband, who she didn't evenknow that well, but she worked
with him and just thought of meevery time she was with him and
she has wonderful intuition andshe definitely did a better job
fixing up than many people.
I had some bad fix ups but itwas about, you know, telling
people outside your circle, likethrough running club or yoga
(10:42):
club or pickleball or whateverpeople do these days.
Speaker 1 (10:45):
I love that.
So like from hot mess to hotyoga 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 awhile of being single and being
a single mom, I'm a superindependent person.
Anyways, I've always been ableto support myself.
I was one of the lucky people.
When you know, the choice todivorce was mine.
I was able to support myselfand my children, so it was much
(11:19):
easier, and I have extensivesympathy for women who are not
in that same situation and Ihelp and talk to those women
quite, quite often.
You can imagine, after so manyyears you kind of develop this
lifestyle and independence thatI almost thought I'm never going
to be able to fit somebody intothis equation anymore because I
(11:41):
got so used to uncomfortablekind of being alone.
I had definitely decided that Iwill be alone before I be with
the wrong person, even though Ikept trying.
So I think, like figuring outhow to integrate someone into my
life although Will made it veryeasy.
He's my husband and then ofcourse, one of the things to
think about is at the time hehad two boys who he was still
(12:04):
caring for and the primaryperson for, and we had to
integrate these kids and thattransition was really hard.
We were much slower with thatthan we were introducing him to
my kids, although in my 10 yearsof dating he was the only
introducing him to my kids,although he I.
In my 10 years of dating he wasthe only person I introduced my
kids to.
So I was not.
I'm a huge believer in it's nota play date.
(12:24):
I think I say in the book, andat 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 toughtransition and I would never
give up our now like extended,beautiful little combined family
(12:47):
.
Speaker 1 (12:47):
But yeah, for those people who may be going through
that, let's dig into that alittle bit more.
The work piece of finding truelove when it is a blended family
you know it's really, it issensitive, it's hard.
Speaker 2 (12:59):
Someone told me it might have even been the kids
therapist that it on averagetakes seven years for a blended
family to feel like a realfamily.
I think we were overachieversnot 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,
(13:20):
like literally talk all everyday, but they're also like both
obsessed with basketball and youknow certain family guy and
certain things that they're veryinterested in.
But we were super careful, likewhen we came together
physically into the same house,which was about a year after we
were together physically intothe same house, which was about
a year after we were togetherand a year before we got married
.
We made sure each kid had hisor her own space with a bathroom
(13:44):
and a bedroom so that no onewas on top of each other.
We tried to treat everybodyequal.
It was a unique situation forus because we're both the
primary parent for the childrenand so we had all the kids with
us all of the time.
So I think in a lot ofrelationships you have time as a
couple or back and forth, andso we didn't have that.
We went.
(14:05):
I went from being a mom of twoto, you know, being a bonus mom
to two others who like and atthis point I mean my step sons
are my everything.
I can't even imagine them notin my life, but I think you do
have to give them time.
It took one of the boys longerthan the other one to kind of
embrace me, and I think you justneed to push, especially if
(14:26):
there is another parent in thepicture, that I'm not here to
replace that parent, I'm just.
My true philosophy is you cannever have enough people that
love you, and especiallynowadays.
So I kind of feel like the morepeople that love you the better
.
And so, you know, just tryingto get that point across.
And eventually you know we gotthere, and now I feel like we
(14:49):
were all in Mexico forThanksgiving and I was like just
looking around our table,thinking like I just love this
family that we built which issomething that's really special.
Speaker 1 (14:57):
I love how it came together, and that might not
happen for everybody, so alittle disclaimer for people who
are going through this right itdoesn't always work this way,
but you also have to work at tomake it work.
Speaker 2 (15:09):
A hundred percent.
There was again lots oftherapists involved and you know
some some, you know mess upsI'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 Italked to a lot of women about.
(15:31):
I do think if you have adultchildren, like truly you know,
if I met Will now and everyone'sout of the house, I actually
think as much as you wanteveryone to come together.
It's harder, actually, becauseour kids growing up in the same
house, even if it was only forfive or seven years, made a huge
difference and I think itbecomes a little bit less
important to be completelyintegrated as you get a little
(15:52):
bit older and your kids areolder.
It's lovely and hopefully yourkids want you to be happy and
welcome whoever your newsignificant other is, but I do
think at a certain point itbecomes less relevant.
Speaker 1 (16:02):
Yeah, for sure, and a little bit, probably more
ingrained into like, oh, they'rereally a part of my life
because I'm an adult and I'vegot this going on over here,
right, what's one thing youlearned 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 makesure this was the right choice,
(16:36):
even though I knew in my gutthat it was.
And he did all this testing.
He was actually an excellenttherapist, 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 notsure I know what you're looking
for in your life, this truepartner.
I'm not sure you'll ever letanyone in enough to be able to,
(16:57):
like, take care of you, likeyou're saying, and that just
stuck with me.
I mean, it was so many yearsago and I it's, it's the most
beautiful.
We take care of each other.
There's, you know, my analogyin the book where, like, one of
the themes is that really strongcouples take care of each other
(17:17):
.
And, like, the analogy is whenthere's waves like, like, if
someone goes under, someonepulls up, and you can't always
be the puller upper, you have totake turns pulling each other
up, because if not, you knowyou're going to either be
exhausted or drown, basically.
So I just we have thiswonderful balance of supporting
and pulling each other up.
I give up like free control tohim, because I trust him so
(17:38):
inherently, and so that wasprobably my biggest revelation
that I was capable of and what arevelation.
Speaker 1 (17:43):
That was to be like thinking perhaps maybe you could
never fully give of yourself tosomeone to take care of you, to
be all the way like 180 degreeturn to say, oh my goodness,
yeah, it is amazing to havesomeone care for you in the way
that you deserve to be cared for.
Speaker 2 (17:59):
Totally, totally.
I'm always sort of thecaretaker, so it's such a nice
feeling to have that, and sothat 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 knowthat 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 dayback in the day was sort of like
matchcom, eharmony and like Jday.
But that J day was justterrible.
As a Jewish woman I was like,oh God, this I'm just.
If this is all that's out therehere, we're in trouble.
(18:36):
But and I found this guy onMatch and we had been emailing
and it seemed fine.
We were meeting at a bar for adrink.
I always tried to like make adate you know short, like not a
first date, like not a wholedinner, not like you know some
kind of you know short thing,whether it's coffee or a drink
or whatever.
(18:59):
It was easier at the time for meto have like some alcohol as I
was continuing to try to movepast this.
But I show up, he doesn't lookanything like his picture.
Like, literally, he had hair inhis picture.
He was completely bald, he waswearing some random turtleneck,
something I don't know, that'sall I remember.
But we were there for fiveminutes and he pulls out what's
called a cease and desist order,not, and that he had gotten it
(19:20):
from Pepsi because or Coke orsomething like that, because he
was selling stuff out of hisgarage and so he wanted me to
look at it as a lawyer and givehim legal advice.
And this is the time whereyou're like, oh my god, thank
God I have young children and Iwas like, oh my god, my
daughter's playing and I was, Ithink I was in and out of there
(19:41):
in eight minutes and likerunning to my car, it was just.
It was like, you know, just oneof those things, that.
But that went so badly and partof it was just he wanted like
some expertise rather than hadany interest in me, but just
generally.
And then he texted me and askedme 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 arewondering out, there is like you
have found true love.
Have you?
In the course of your researchor talking to other people?
Is it like?
Have you found folks doing thesame thing in midlife?
Like finding?
Speaker 2 (20:21):
their person, absolutely.
I have a couple of friends whoare on a second marriage, some
of who I interviewed the book,some of who I have not, and they
have definitely found theirperson, who they say was more of
their person than in the firstmarriage.
Because I also feel like, Imean, who I am at 45 is very
different than who I am at 28 orwhatever, and that's why I'm
(20:44):
also telling my kids to like,take your time, you do not have
to get married by the timeyou're 30.
Like you know, let's figure outwho you are and what you want
and and all the things.
So but but yeah, I mean, and Iwill say, the vast majority of
people that I interviewed forthe book the first time, I think
only one of them's gottendivorced since I interviewed
(21:05):
them, and those are some likethere's some serious longevity
in those marriages, but I do,I've sort of become like I think
when you're, like the firstperson divorced and I'm a lawyer
, anyways, I talked to a lot ofwomen who get divorced, so they
might be 30, 40, 50, 70.
I talked to someone 70 last week.
You know, it just depends, butI help them.
(21:25):
Try to understand.
You're at the bottom of thishill and you're going to get
over it and it's so beautiful onthe other side and all of the
things.
But you also want to get hopethat they're going to be able to
find love again, if that'ssomething that they're going to
be able to find love again, ifthat's something that they are
interested in, and so I thinkI'm a symbol of that for a lot
of people, which I reallyappreciate, because I always say
everyone needs a will, which ismy husband's name, and they
(21:48):
should all have a will in theirlife.
Speaker 1 (21:49):
Everybody should have a will.
Wait, not that type of will,this type of will.
This kind of will exactlyThroughout this journey, other
than finding will what was adefining moment for you.
Speaker 2 (22:03):
I think that I originally, right when I got
divorced, I started datingsomebody and it was symbolic of
some of my bad choices.
He turned out to have adrinking problem and it was
somebody that I think I did meethim online.
Actually, I only dated like twopeople that I had met online,
(22:25):
but I had.
I met him online and he was alawyer and we definitely clicked
.
There was like chemistry, itwas like one of those things.
But I found myself overlookingthese bright red flags.
I found myself overlookingthese bright red flags and, like
, I even found out later that hehad told me he was divorced but
he was really only separated,and so, you know, I was.
(22:47):
I was strong enough to like endthat and walk away pretty
freaking quickly, like comparedto before, but I definitely felt
that was a defining moment.
I'm not going to just findsomebody, even if there's
chemistry there, if the otherpieces of the puzzle are not
there for me, and I know what Ineed now and I need to be
careful to not go down that badroad again, and so that was
(23:11):
really a defining moment.
Speaker 1 (23:13):
That was probably like a year into, maybe two,
into being divorced, and I waslike, okay, like a year into,
maybe two, into being divorced,and I was like, okay, yeah, so
where my, where my coach braingoes for my listeners is you?
You needed to work on yourselffirst before you could figure
out what you want and you justhop 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 overthe 10 years I took lots of
breaks from dating.
There was many times where I'mlike I'm not dating anybody for
six months, I'm just focusing onme and my kids.
And I had busy times at workwhen I was traveling a lot and
all of that, and I kind of tookbreaks from the process.
(23:49):
And I would say the otherdefining moments were me.
For example, my oldest was BobMitzvah, 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 withme with my kids anyways, but
even without my kids like towork thing, this it was like too
stressful to me and I never wasreally in a relationship where
like it had reached the level of, okay, we can do this.
And so like showing up aloneall the time and like being the
odd person out really made mekind of assess my life but also
(24:23):
realize like, okay, I'm on myown best date and I can do this.
And I had lots of hystericaldating stories to share a
cocktail hour.
So I was very entertaining andyou know, I just I found that
every time I did it it got alittle bit easier.
Speaker 1 (24:38):
You just said a nugget in there which I want
people to like go back in hereis I was my own best date, and I
think that's how you become thebest version of yourself.
For other people is to becomeyour own best date, and then you
can figure out how other peoplefit into that Exactly.
Speaker 2 (24:53):
Exactly I really I wanted to be.
I did feel like when I met Willthat 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 thebook is he makes me a better
person.
Like he's such a good personand he's expanded me culturally
and like with arts and all kindsof stuff that I feel like you
(25:17):
know makes me a better person.
He was so encouraging to writethis book or whatever it is that
I want to do in my life.
He very much supports me and Isee him always doing well and
doing good and all of that andit 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 notethat I wrote for my daughter.
I was watching a movie, right,all the good things come from
movies.
It was about finding the rightperson and there were four
questions to ask Is he kind oris she kind?
Can you tell him everything inyour heart?
Does he help you become thebest version of yourself?
(25:52):
And then the final one is canyou imagine him as the father of
your kids?
But that plays out too, ifyou're a blended family, like a
supporter of your kids, let'ssay.
Speaker 2 (26:03):
But I thought those are easy.
Four questions, those arefabulous.
Speaker 1 (26:06):
And so my daughter's 25.
My son's 27.
But I was like oh, I'm writingthose down and tucking those
away for later.
I don't think she listens tothis.
Oh, she's not going to hearthose 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 abouthow many of my friends you know
we all sort of have adult.
I have tons of friends who havethe kids the same age as our
kids and so many of them havebought the book for their kids
and I've heard from so many ofthe kids and because I think
they hear me my kids talk abouthow they've learned so much from
the process and things likethat.
A friend of mine uses this term,noah's Ark theory, which is
kind of the thought that in ourworld everyone feels like you
(26:48):
have to be matched up in apaired up, and so you kind of
have this inclination like it'sbetter to have someone in my
life rather than to be alone.
And what I'm trying to tell mykids is, first of all, you're
not ready to be a partner untilyou're your best version of
yourself.
Like for Valentine's Day thisyear, I sent them all $100, all
four of them and I said takeyourself out to do something
(27:10):
yourself and focus on yourselffor at least an hour, because
you are your best Valentine andyou're not going to be able to
be a Valentine to someone elseuntil you do that.
And so they're all excitedabout the money, of course, but
still I think they got themessage.
And so the goal is like for thekids to understand that they
don't need to fall into this.
I need, need a partner, I needa date, I need whatever.
(27:33):
They need to focus onthemselves, you know, put your
mirror on yourself, and then wecan 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 mydaughter's brain too.
It's like you don't needsomebody else to complete you
right yourself first.
Then you find somebody whocompliments you doesn't complete
you compliment oh, I like thattoo.
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 themrewrite it exactly.
Vacation exactly together mywife 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 forthe beach so she has some noreen
.
I'm like listen to this podcastepisode first and then I've got
something for you Perfect.
Speaker 2 (28:18):
Perfect and it's been fun.
I started a podcast with my22-year-old and he's done
podcasts before, but we'recalling it I Love you More.
It's available on Spotify andApple and we're talking about
all things dating, relationshipsand love generationally and I
will be honest that it's broughtme more joy than anything I've
(28:41):
ever done in my life just havingthese super in-depth
conversations with Zach.
But at the same time, I havelearned so much and just how you
know the way these kids willapproach people on Tinder or
Hinge but not walk up to them ata bar, I mean, and it's just
how swiping's almost can be agame sometimes and it's just
(29:05):
this.
It's just a very.
I mean I've learned a millionthings, but it's just been this
interesting journey and I amlearning a lot and I think that
modern love and modern datingfor our kids looks different and
I actually am like promoting tomy four like let's date in the
wild people, like let's deletethe apps and let's put yourself
(29:25):
out there and do things becauseyou know maybe meeting people
will actually be good for you,like in real time.
Speaker 1 (29:33):
Exactly.
Forget the swipe left and swiperight.
How about you know?
Be right in front of somebodyinstead?
I love that.
So I do have some youngerlisteners who listen to the show
.
I'm just curious what are themain differences that you and
your son talk about on that?
Speaker 2 (29:50):
show so far.
We just started it and he'sgraduating next week, so it's a
little bit on hold for a minute.
But you know, the maindifference is literally, I would
definitely say, the technologyand I would just say the number
of apps and how they'reformatted.
And we just talked a lot, youknow, like what you have to put
(30:12):
in and how people are trying tocultivate a vibe rather than
authenticity trying to cultivatea vibe rather than authenticity
and we've talked a lot aboutthe fact that being authentic is
really the foundation for astrong relationship.
So, in my head, meetingsomebody online like that, when
you're not being your true self,is very challenging from like a
(30:33):
foundational standpoint, andyou know he definitely agreed
with that.
We talked a lot about fix-ups, Ithink last episode and that and
you know they're not remotelyinto that whole thing, I mean.
But he's 22 and even my 25, 27,they've never really been fixed
up and and I was, so I said Ithink I asked him last time
(30:55):
would you let me fix you up?
And he's like you know, maybe Ido think that they might want to
trust like people in theirlives, to maybe fix them up at
work or in other places and seehow that goes.
I do sense, though, that thereis this kind of burgeoning
(31:17):
joining and like turning awayfrom the apps, and I think that,
hopefully, leaving college willwill change that, at least for
like my baby, and hopefully forothers, and so you know, it's
also I think there's a lot oflearning that they're trying to
do like.
Zach was basically explaininglike I'm 22, I'm not the best
(31:37):
version of myself.
He's a super self aware kid,and he was saying that I know
I'm not ready to be in arelationship, I know I've made
wrong choices, and so I feellike, even if I dated somebody
now, it wouldn't be my personforever, and so I might, when
I'm ready for that, I mightapproach 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 peoplethrough your circle of friends,
which is small, or at a barright, right.
The kids are like so true likeeven 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 bestsolution yeah, it's part and
parcel of everything, a littlebit of both.
They're like a really goodrecipe the apps, meeting people
going out there and just talkingto anybody, those types of
things.
So that's, I think that's howyou 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 kindof go all in and I think you
know, do the apps.
I did like a lunch date service.
I did like Jewish speed datingone day, which that was also a
very funny, terrible story, youknow.
Do the apps, I did like a lunchdate service.
I did like Jewish speed datingone day, which that was also a
very funny, terrible story.
(33:02):
You know, I did all the things.
It's like I really was.
You know, and I'm superinterested in like matchmakers
and things like that, because Ilove I'm.
I one of my goals is to likeinterview and talk to more
matchmakers because I think thatthat's such an interesting
concept.
Like my friend, anne has thisamazing intuition, but I feel
like you really have to haveintuition because when you're a
(33:24):
matchmaker, your pool's only asgood as the people that are in
it.
So if you're trying to justmatch up people cause they're in
your pool, that's not as goodas if you like I recently set
somebody up because it was sortof a similar situation.
They recently set somebody upbecause it was sort of a similar
situation.
They're both in New York andevery time I see him, I think of
her, which is like weird, andso I?
I haven't.
They haven't gone out yet butwe'll see what happens.
Speaker 1 (33:45):
Yeah, all right, before I let you go, heidi, the
one question I always love toask folks is what is your empty
nest, or what is your life motto?
And perhaps, coming out of thiswhole journey, what's a couple
of word sentence that's likethis is this defines?
Speaker 2 (34:04):
my life in this moment.
That's a.
That's a tough, interestingquestion.
So one of my favorite lifemodel, life sayings I don't know
why I couldn't think of theword is actually Comparison is
the.
Thief of Joy, and I will saythat my journey taught me that
(34:26):
and I still am working on it.
It's not something, especiallyas an empty nester.
You can see kids getting jobsand being successful while yours
are struggling and you reallycan keep you up at night in not
good ways and I am constantlyreminding myself that comparison
is the thief you know, is thethief of joy, and I tell my kids
(34:47):
.
And so social media makes thathard.
And and then the other thingthat kept me going is someone
bought me like a little posterwhen I got divorced that said,
when the caterpillar thoughtlife was over, she became a
butterfly and I still have likea little cutout of it that I
keep next to my desk and I thinkit's just that's about hope and
(35:08):
the whole reason that I amgoing around talking about this
book.
I mean, I have a verysuccessful legal career, I love
my day job, but I feel likewe're in a time where spreading
love and hope is just soimportant and if I can just give
one person hope that they mayfind 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 HeidiFriedman, helping people with
hope of finding their true love,and, if you want it, the book
Love Lessons 104 Dates andStories that Led Me to True Love
is available on amazoncom rightnow.
Check it out, put it in theshow notes for folks.
Heidi, it's been an absolutepleasure having you on.
Speaker 2 (35:49):
Thank you so much.
This was so fun and I'm goingto remember those four questions
.
I love those four questions.
That's perfection.
Tell your daughter she needs tolisten to you?
Speaker 1 (36:00):
I don't know.
Speaker 2 (36:01):
You're planting seeds .
You're planting seeds, they'llgrow, I promise.
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