Navigating Dating Apps Mid & Post Divorce

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In this episode, I’m peeling back the curtain on my personal journey through dating apps during and after my divorce. Trust me, it’s been a ride. From steamy sexting surprises to real-life lunch dates gone sideways (hello, napkin-mopping man), I’m opening up about the hilarious, cringe-worthy, and totally unexpected moments that come with putting yourself out there again.

If you’re navigating dating apps after a long relationship, trying to rebuild confidence, or just need a laugh and a little validation, this episode is for you. I share what I’ve learned, how I handled the red flags (and the red faces), and why your healing journey truly matters when it comes to who you attract and how you show up. This one’s honest, fun, and might just remind you that you’re not alone in this wild dating world.

 

Episode Highlights:

[0:21] - Why I’m sharing these dating stories now: laughter, growth, and real talk
[1:00] - Sexting surprises: the guy who actually asked, "How can I help?"
[2:27] - Grateful for the "guy manual" and what I learned about generosity
[4:46] - Married men on the apps? Yep. And how I handled that turn-off
[6:15] - Discovering who I was becoming through all of this
[7:40] - My first post-divorce in-person date: lunch, Rolexes, and buckets of sweat
[9:40] - The post-date voicemail saga: when he told his mom about me
[11:02] - Tennis clinic commentary: Was I intimidating? (Apparently, yes!)
[12:55] - Wrapping up with a promise to share more stories soon

 

Links & Resources:

Be sure to follow, share, and leave a comment if this show resonates with you! Send me a message at podpage.com/themusicoflife to share your experiences, or to leave a comment. I'd love to feature it in a future episode.

Episode Transcript

Caryn Portnoy (00:02):
Karen, hi everyone, and welcome to the
music of Life. I'm your host.
Karen Portnoy, before I get intothis episode, please comment,
ask questions, share some ofyour experiences, and don't
forget to subscribe.
I wanted to lighten things up abit. It's funny because some of

(00:25):
my divorced friends, you know,we all have dating stories and
sex stories and things likethat. And while I haven't had
sex in the last five years, andI'm pretty open about that, you
know, I I have had intimateconversations with people online
during my divorce, and therewere some funny stories that

(00:46):
came out of that. So I justwanted to share a couple that
were kind of funny and fun andthings like that. I will say
that the first one that standsout to me was, I would say it
was somewhere around halfwaythrough my divorce, and I was
getting on some of these datingapps, and, you know, just kind

(01:09):
of getting the lay of the landand seeing what was up in the
dating world and what I had tolook forward to, and things like
that. I remember I connectedwith this guy who was super
attractive, and we were textingfor a bit and kind of getting to
know each other a little. Andthen we kind of like started
sexting with each other. And itwas interesting because, you

(01:34):
know, it was getting kind of hotat some point, and I was
struggling to finish, and so Iwas trying to text as this was
happening, and like, without anyhesitation at all. The first
thing he said was, how can Ihelp? And that blew me away,

(01:55):
because I had no experiencewhatsoever with a generous
lover. I mean, my entiremarriage was not about how he
could pleasure me and anythinglike that. So this was a brand
new experience, and it blew meaway, because I never knew that

(02:15):
anybody could care that much.
Youand this was a stranger. This
was somebody that you know andand let me just say, and I'm so
grateful I have a guy for a veryclose guy friend who, for
decades, has always kind ofgiven me the lay of the land

(02:39):
when it comes to the guy'sperspective. So, you know, we
joked around years and years agoabout, you know, the quote,
unquote guy manual. So we wouldtalk about different things that
that happened, and he, you know,I would say things like, Oh, is
that in chapter 12? And, youknow, so it's been this running
joke for all these decadesabout, you know, what guys

(03:01):
intentions are, and how theyoperate, and what they think,
and all that stuff. So I'vealways been so grateful for that
kind of input and perspectiveand knowledge anyway. So my
friend kept telling me how muchguys enjoy giving oral sex to
women, and I don't have thatexperience really at all. And

(03:23):
whatever experience I have withit was more like in my 20s, not
my 50s. But I digress. Soanyway, this guy who said, How
can I help? I was so taken abackby that comment, in the moment
that everything just becameabout that I was just, I

(03:44):
couldn't help but just take thatin with such gratitude that
somebody cared that much to wantto pleasure me, or, you know,
through texting or sexting. Sowe kind of eventually spoke on
the phone, and actually it wasthe one time that we spoke on
the phone, and when, when Iheard his voice, he sounded like

(04:04):
a 12 year old. I mean,seriously, this was not the same
guy that was in the pictures ononline. And so I didn't care,
because, I mean, look, I wasn'tmeeting anybody in person
anyway, and you know, this wasmy way of, kind of testing the
waters and seeing what was outthere. And, you know, obviously
I never spoke to that guy again,because, like, hello, if he

(04:28):
sounds like a 12 year old on thephone, I can only imagine what
he looked like in person, andthat was not happening. So it
didn't matter, youbut my my guy friend, who I'm
talking about now, he was veryinstrumental in help guiding me

(04:51):
through the dating apps.
Because, you know, I was, I wasnew to all of this. I didn't.
Know, you know what was real andwhat wasn't, or the extent of
how badly it wasn't real. And hereally guided me through who the
married guys were and who thecheaters were and who the liars

(05:12):
were and things like that. I didget a good education, I have to
say. And I always thank him forthat, because, you know, it was
very helpful to me. Wasn't 100%for sure, but it was definitely
eye opening and educational forme and and stuff like that. So I
was surprised at how manymarried men reached out to me

(05:35):
while, you know, going throughmy divorce and everything, and
as soon as I found out that theywere married, I was so turned
off and so grossed out. And youknow, I had nothing to do with
them after that. But it was, itwas alarming to me, how many
people were ended up beingmarried. So to anyone who's

(05:56):
married and listening to this,watch out. You never know. Also,
it was very helpful to me toconnect with all these people,
because it really helped me toshape who I was and who I wanted
to be for myself going forwardand once my divorce was done and

(06:18):
I was ready to meet people inperson, like I didn't know how I
was going to be. I didn't know,you know, would I be confident?
Would I not be confident? WouldI be I don't know. I just I
didn't have a grip on the datingthing during my divorce and
beyond. So I will say that onceI moved out of my house, which

(06:41):
was the only way my divorce wasgoing to end, and I continued on
my healing journey and all ofthat, I would you know, I was
finally at a place of feelingconfident within myself and
knowing who I was, and havingdone so much healing work and
all of that, that when I wasactually ready to meet somebody
in person. I was, I was reallygood in myself, you know, just I

(07:07):
was good. So I met this guy onone of the apps, and we spoke on
the phone for like two weeks, Iguess, yeah, I think it was
around two weeks. And this wasearly on. This was the first guy
that I met in person since mydivorce, and he had good banter
on the phone, and he was, he wasa little mysterious, but, you

(07:30):
know, seemed confident and allthese things, and he piqued my
attention enough to continue aconversation for two weeks. Then
he wanted to get together, so wemade a lunch date, which was
fine, and he was local to whereI was living, so it wasn't so
out of whack that, you know,either of us had to travel far,

(07:53):
and I showed up to This date,and I don't know it's very
weird. II was very comfortable in
myself. I was confident, I was Iwas just myself. I there was no

(08:15):
pretense, there was no show,there was no mask, there was no
nothing. I was just comfortablein my own skin. I was, you know,
happy. I was present. I waslooking forward to getting to
know him better, whatever. Andlet me just tell you, we sat
across the table, and this guywas sweating buckets, when I
tell you, dripping sweat likekept taking his napkin to wipe

(08:40):
his head and his face. And Ifelt so bad for him, and I
didn't know why he was thatsweaty, but it was very
apparent. So, you know, look, Ieat my salad. I was fine. I was,
you know, trying to makeconversation. And I found that
he was very focused on talkingabout his money and the 14

(09:02):
Rolexes that he has, and theAlfa Romeo car that he was
driving, and all the stuff. AndI told him over the phone, as we
started talking about money andstatus and material things and
stuff. And I was very clear I'mnot about that. I mean, look,

(09:22):
money is great, and I valuemoney, and I'm, you know, I
think it's it's important, andit's important to talk about it
and be on the same page aboutit. But do not show off to me as
if your money is going toimpress me, because I'm not
impressed by that. Show meyou're a good person. Show me
that you have good character,that you have integrity, that

(09:43):
you have good values and ethics,and that means so much more to
me than how much money you havein the bank. But anyway, so he
was really boasting a lot aboutthe things he had, and I was.
Just really, really turned offby the end of the date, I was
just not into him at all. And sowe parted ways and and I went

(10:06):
home. And I don't know if it waslater that day or the day after,
but he ended up calling me, andhe was telling me that he told
his mother about me. I was like,What? What are you kidding me?
So I mean, that was an obviousturn off, red flag, whatever.
And he he kept calling me fordays after, and I was trying to

(10:30):
let him down gently, and it wasnot working. He was still coming
on pretty strong. And finally, Ihad to pull the the bitch card
out, because he wasn't gettingthe hint at all. And I said to
him, I don't have romanticfeelings for you. And he was
like, ouch, that was cold.

(11:02):
And I, you know, I'm sorry. Ididn't mean to be a bitch, but
he wasn't getting the hint. Andand what else is a woman to do?
Luckily, he finally got thehint, and I never heard from him
again, but, like, that was crazyanyway, so I ended up playing
tennis. I play tennis once aweek, and I've been in the same

(11:22):
clinic for years and years. Andthis guy, this guy that is in my
clinic that I play withregularly, he's this big Italian
guy, and he's so flirty and he'sfunny and he's charismatic, and,
you know, everyone loves playingwith him and all this stuff. So
he was asking me, you know, ifI've been on any dates recently.

(11:45):
And so I told him about thisencounter and and how this guy
was sweating so much, and hegoes, car, you intimidated the
guy. And I was like, What areyou talking about? And he's
like, you, you're intimidating.
And look, I don't perceivemyself that way, but I
understand what he was saying,but, you know, it was a very
awkward date because of it. Andso anyway, I got a laugh out of

(12:08):
what this guy was saying, but Idon't know. I try to be normal
and regular and disarming andsafe for people, and you know,
I'm not looking to beintimidating to people or
anything like that. But look, itis what it is. And if he was
intimidated, then I want to saythat's on him. I don't think I

(12:28):
portrayed myself in a way to beintentionally intimidating to
him or anybody. But, you know, Ican't help what he felt on his
side. So anyway, as I come upwith more stories and more
experiences, I'll I'll sharemore, but I think that's good
for today. So thanks forlistening. I'll see you the next

(12:50):
one. Please join me everyThursday for a new episode. You
can reach my website at podpage.com/the, music of life.
Feel free to leave your emailaddress. You can also leave a
voicemail and share any kinds ofstories or experiences or
anything that you'd like to talkabout. I promise I will keep you

(13:11):
anonymous, but I assure you thatwhatever experiences or stories
you leave for me, you are notalone, and I would love to share
that with other people who arealso going through similar
things. Thanks again forlistening. I'll see you in the
next episode. You.