Dating As A Single Dad: Finding Love After Raising His Kids
Seeing Other People
Ilana Dunn
4.5 • 608 Ratings
🗓️ 23 April 2026
⏱️ 47 minutes
🧾️ Download transcript
Summary
Ryan is a 43-year-old single dad living in a small coastal town in Mississippi, navigating dating with a uniquely small dating pool — and a clear idea of what he wants. After two divorces, gaining full custody of his kids, and years focused on raising them, he’s now approaching life as an empty nester and ready to find a partner.
In this Unfiltered episode, Ryan shares what it’s like dating long-distance, hiring a matchmaker, why he’s intentional about keeping doors open, and the moment he ended a relationship after his partner crossed a boundary with his kids. He opens up about resilience, starting over, and balancing hope with acceptance when dating later in life.
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Transcript
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| 0:00.0 | Yes, I am Ryan. I am 43 years old. I live in Gulfport, Mississippi, which for those of you who aren't very good with geography, it is South Mississippi. I am eight miles from the Gulf of Mexico, 80 miles from New Orleans, 60 miles from Mobile, just tipped away in a great little place. |
| 0:24.2 | I'm a third generation in multiple family businesses. I have two kids at 1917. So any of you empty nesters out there, I'd like to know what it's like because I'm about to experience it in six months and just don't know what to |
| 0:37.9 | expect. And Alana, I'm just happy to be here, happy for the opportunity. I'm so happy to have |
| 0:43.4 | you. Thank you. I love hearing from people who aren't in New York City. You know, New York City's great. |
| 0:49.9 | There are a lot of us here, but not everyone is here. And dating in New York is very, very different from dating in other parts of the country. And I can't wait to hear about what your dating and relationship experiences have been in what I can only imagine feels like such a different world. |
| 1:08.9 | Oh, it's, I mean, yes, it is. I mean, being a, one of 2,000 Jews in the |
| 1:16.1 | whole state of Mississippi, obviously you can tell that I'm not going to date family. So I have to |
| 1:21.5 | kind of venture out to, to, you know, I mean, see, see what, see what it's like out there, I guess, |
| 1:27.1 | quote in the real, you know, in the real world. Yeah, I've, I mean, see, see what it's like out there, I guess, quote in the real, you know, in the real world. |
| 1:30.1 | Yeah, I've, I've tried Jewish speed dating, which I love. I have zero expectations going into it. |
| 1:39.3 | I did strike once on that, had a 15-month relationship. |
| 1:44.8 | And we just got to the point where it was like, okay, we got to figure out what we're |
| 1:48.8 | going to do. |
| 1:49.3 | And we just went separate ways. |
| 1:52.5 | And I mean, she was out of state and we were trying to figure out how we were going to commute. |
| 1:56.7 | And like I said, just make it work. |
| 1:58.5 | And at the end of the day, we just had different, uh, different response. |
| 2:03.3 | I mean different, different, different responsibilities, uh, in, in our home states. |
| 2:07.7 | And it just didn't work out. |
| 2:10.0 | I hired a matchmaker, um, which was fantastic. |
| 2:13.8 | It was definitely a eye opener experience. |
| 2:17.6 | I mean, everybody watched the, uh, a lees seems like. So it was like, I heard that. And my kids were like, yeah, why don't you hire a matchmaker? Like, it's time for you to have a girlfriend. I'm like, what? They're like, yeah, it's time for you to have a girlfriend. I was like, okay, fine. If it's time for me to have a girlfriend, it's time for me to have a girlfriend. So I went ahead and, yeah, I hired a matchmaker. |
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