Navigating Dating Apps Mid & Post Divorce

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.

Transcript

Caryn Portnoy: 0:02

Karen, hi everyone, and welcome to the music of Life. I'm your host. Karen Portnoy, before I get into this episode, please comment, ask questions, share some of your experiences, and don't forget to subscribe. I wanted to lighten things up a bit. It's funny because some of my divorced friends, you know, we all have dating stories and sex stories and things like that. And while I haven't had sex in the last five years, and I'm pretty open about that, you know, I I have had intimate conversations with people online during my divorce, and there were some funny stories that came out of that. So I just wanted to share a couple that were kind of funny and fun and things like that. I will say that the first one that stands out to me was, I would say it was somewhere around halfway through my divorce, and I was getting on some of these dating apps, and, you know, just kind of getting the lay of the land and seeing what was up in the dating world and what I had to look forward to, and things like that. I remember I connected with this guy who was super attractive, and we were texting for a bit and kind of getting to know each other a little. And then we kind of like started sexting with each other. And it was interesting because, you know, it was getting kind of hot at some point, and I was struggling to finish, and so I was trying to text as this was happening, and like, without any hesitation at all. The first thing he said was, how can I help? And that blew me away, because I had no experience whatsoever with a generous lover. I mean, my entire marriage was not about how he could pleasure me and anything like that. So this was a brand new experience, and it blew me away, because I never knew that anybody could care that much. You and this was a stranger. This was somebody that you know and and let me just say, and I'm so grateful I have a guy for a very close guy friend who, for decades, has always kind of given me the lay of the land when it comes to the guy's perspective. So, you know, we joked around years and years ago about, you know, the quote, unquote guy manual. So we would talk about different things that that happened, and he, you know, I would say things like, Oh, is that in chapter 12? And, you know, so it's been this running joke for all these decades about, you know, what guys intentions are, and how they operate, and what they think, and all that stuff. So I've always been so grateful for that kind of input and perspective and knowledge anyway. So my friend kept telling me how much guys enjoy giving oral sex to women, and I don't have that experience really at all. And whatever experience I have with it was more like in my 20s, not my 50s. But I digress. So anyway, this guy who said, How can I help? I was so taken aback by that comment, in the moment that everything just became about that I was just, I couldn't help but just take that in with such gratitude that somebody cared that much to want to pleasure me, or, you know, through texting or sexting. So we kind of eventually spoke on the phone, and actually it was the one time that we spoke on the phone, and when, when I heard his voice, he sounded like a 12 year old. I mean, seriously, this was not the same guy that was in the pictures on online. And so I didn't care, because, I mean, look, I wasn't meeting anybody in person anyway, and you know, this was my way of, kind of testing the waters and seeing what was out there. And, you know, obviously I never spoke to that guy again, because, like, hello, if he sounds like a 12 year old on the phone, I can only imagine what he looked like in person, and that was not happening. So it didn't matter, you but my my guy friend, who I'm talking about now, he was very instrumental in help guiding me through the dating apps. Because, you know, I was, I was new to all of this. I didn't. Know, you know what was real and what wasn't, or the extent of how badly it wasn't real. And he really guided me through who the married guys were and who the cheaters were and who the liars were and things like that. I did get a good education, I have to say. And I always thank him for that, because, you know, it was very helpful to me. Wasn't 100% for sure, but it was definitely eye opening and educational for me and and stuff like that. So I was surprised at how many married men reached out to me while, you know, going through my divorce and everything, and as soon as I found out that they were married, I was so turned off and so grossed out. And you know, I had nothing to do with them after that. But it was, it was alarming to me, how many people were ended up being married. So to anyone who's married and listening to this, watch out. You never know. Also, it was very helpful to me to connect with all these people, because it really helped me to shape who I was and who I wanted to be for myself going forward and once my divorce was done and I was ready to meet people in person, 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? Would I be I don't know. I just I didn't have a grip on the dating thing during my divorce and beyond. So I will say that once I moved out of my house, which was the only way my divorce was going to end, and I continued on my healing journey and all of that, I would you know, I was finally at a place of feeling confident within myself and knowing who I was, and having done so much healing work and all of that, that when I was actually ready to meet somebody in person. I was, I was really good in myself, you know, just I was good. So I met this guy on one of the apps, and we spoke on the phone for like two weeks, I guess, yeah, I think it was around two weeks. And this was early on. This was the first guy that I met in person since my divorce, and he had good banter on the phone, and he was, he was a little mysterious, but, you know, seemed confident and all these things, and he piqued my attention enough to continue a conversation for two weeks. Then he wanted to get together, so we made a lunch date, which was fine, and he was local to where I was living, so it wasn't so out of whack that, you know, either of us had to travel far, and I showed up to This date, and I don't know it's very weird. I I was very comfortable in myself. I was confident, I was I was just myself. I there was no pretense, there was no show, there was no mask, there was no nothing. I was just comfortable in my own skin. I was, you know, happy. I was present. I was looking forward to getting to know him better, whatever. And let me just tell you, we sat across the table, and this guy was sweating buckets, when I tell you, dripping sweat like kept taking his napkin to wipe his head and his face. And I felt so bad for him, and I didn't know why he was that sweaty, but it was very apparent. So, you know, look, I eat my salad. I was fine. I was, you know, trying to make conversation. And I found that he was very focused on talking about his money and the 14 Rolexes that he has, and the Alfa Romeo car that he was driving, and all the stuff. And I told him over the phone, as we started talking about money and status and material things and stuff. And I was very clear I'm not about that. I mean, look, money is great, and I value money, and I'm, you know, I think it's it's important, and it's important to talk about it and be on the same page about it. But do not show off to me as if your money is going to impress me, because I'm not impressed by that. Show me you're a good person. Show me that you have good character, that you have integrity, that you have good values and ethics, and that means so much more to me than how much money you have in the bank. But anyway, so he was really boasting a lot about the things he had, and I was. Just really, really turned off by the end of the date, I was just not into him at all. And so we parted ways and and I went home. And I don't know if it was later that day or the day after, but he ended up calling me, and he 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 obvious turn off, red flag, whatever. And he he kept calling me for days after, and I was trying to let him down gently, and it was not working. He was still coming on pretty strong. And finally, I had to pull the the bitch card out, because he wasn't getting the hint at all. And I said to him, I don't have romantic feelings for you. And he was like, ouch, that was cold. And I, you know, I'm sorry. I didn't mean to be a bitch, but he wasn't getting the hint. And and what else is a woman to do? Luckily, he finally got the hint, and I never heard from him again, but, like, that was crazy anyway, so I ended up playing tennis. I play tennis once a week, and I've been in the same clinic for years and years. And this guy, this guy that is in my clinic that I play with regularly, he's this big Italian guy, and he's so flirty and he's funny and he's charismatic, and, you know, everyone loves playing with him and all this stuff. So he was asking me, you know, if I've been on any dates recently. And so I told him about this encounter and and how this guy was sweating so much, and he goes, car, you intimidated the guy. And I was like, What are you talking about? And he's like, you, you're intimidating. And look, I don't perceive myself that way, but I understand what he was saying, but, you know, it was a very awkward date because of it. And so anyway, I got a laugh out of what this guy was saying, but I don't know. I try to be normal and regular and disarming and safe for people, and you know, I'm not looking to be intimidating to people or anything like that. But look, it is what it is. And if he was intimidated, then I want to say that's on him. I don't think I portrayed myself in a way to be intentionally intimidating to him or anybody. But, you know, I can't help what he felt on his side. So anyway, as I come up with more stories and more experiences, I'll I'll share more, but I think that's good for today. So thanks for listening. I'll see you the next one. Please join me every Thursday for a new episode. You can reach my website at pod page.com/the, music of life. Feel free to leave your email address. You can also leave a voicemail and share any kinds of stories or experiences or anything that you'd like to talk about. I promise I will keep you anonymous, but I assure you that whatever experiences or stories you leave for me, you are not alone, and I would love to share that with other people who are also going through similar things. Thanks again for listening. I'll see you in the next episode. You.