What It’s Really Like Being a Single Man at 37
Seeing Other People
Ilana Dunn
4.5 • 608 Ratings
🗓️ 15 January 2026
⏱️ 59 minutes
🧾️ Download transcript
Summary
Brandon, from the episode “How to Not Lose Hope That Your Person Is Still Out There,” is back today to share what’s shifted since we last spoke. We talk about dating in your late 30s after divorce, dating app burnout, asking someone out in real life, and the quiet pressure of timelines around marriage and kids. Brandon opens up about holding hope while preparing for different futures, redefining success, and learning how to build a meaningful life—even when it doesn’t look the way you imagined.
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Transcript
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| 0:00.0 | All right, you guys, I am so excited for today's conversation. |
| 0:07.0 | Nothing makes me happier than when an unfiltered guest comes back. |
| 0:12.4 | And I got a great email, I think, like last week or two weeks ago from a previous |
| 0:17.9 | unfiltered guest. |
| 0:19.5 | He was on an episode in 2024 called How to Not Lose |
| 0:24.0 | Hope that your person is still out there. And I'm really excited to welcome you back. So Anonymous, |
| 0:31.0 | welcome back. Yes. It's nice to be back. Thank you for having me. I really couldn't be happier |
| 0:37.1 | to have you. And last time we spoke, |
| 0:39.5 | and I was just listening back to the episode, actually, and it was a really, really great conversation. |
| 0:43.7 | I'm going to have it linked in the show notes so everyone can, you know, get a refresher if they're new and |
| 0:47.9 | haven't heard it. It's definitely one worth listening to. But we talked about just a little recap, |
| 0:53.4 | your marriage to the love of your life ended in divorce. And we talked about just a little recap, your marriage to the love of your life, |
| 0:55.5 | ended in divorce. And we talked about your healing journey. We talked about getting not necessarily |
| 1:01.5 | back out there, but getting out there in the dating world as a man in your early 30s at the same |
| 1:07.2 | time as moving halfway across the country. |
| 1:17.6 | And I think what I took away really was like your self-awareness of where you were at and how patient you were being with the whole dating process, even though we don't want |
| 1:23.3 | to be patient. And it's really hard to be patient. But there were a lot of really good |
| 1:27.2 | takeaways. |
| 1:27.9 | So why don't you give us a little insight into what made you want to come back? Like, |
| 1:34.3 | why are you here now? Yeah. So obviously the first conversation we had was great. By the way, |
| 1:40.9 | my name is Brandon. I live in Houston, Texas. Good to see everybody. But I had such a great |
| 1:46.7 | conversation with you the first time and honestly have continued to learn so much over the last year |
... |
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