What Dating as a 34-Year-Old Guy Is Really Like
Seeing Other People
Ilana Dunn
4.5 • 608 Ratings
🗓️ 26 November 2025
⏱️ 64 minutes
🧾️ Download transcript
Summary
In this Unfiltered, Harry comes back to talk about what dating, healing, and growing in your mid thirties has actually looked like for him this past year. We get into how friendships shift as everyone around you moves into new phases of life, what it feels like to be the single one in the group, and how he has learned to sit with discomfort instead of running from it. He shares how hobbies and community have supported him, how he thinks about showing up in the world, and what has been the most meaningful lesson he is taking with him into his next chapter.
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Transcript
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| 0:00.0 | My name is Harry. This is the third time I've been back on Unfiltered for anyone who hasn't |
| 0:08.3 | listened. And I'm a 34-year-old single man living in Washington, B.C. through very interesting |
| 0:15.7 | time in life, considering we are 40 days or more into a government shutdown and I'm a government |
| 0:22.5 | employee. |
| 0:23.5 | So happy to be here and chatting today, Alana. |
| 0:27.8 | Which, first of all, thank you for coming back a third time. |
| 0:30.8 | I mean, I'm so honored anytime anyone wants to come on once. |
| 0:34.0 | And when I posted the other week saying I was looking for guests and you DM me and you were like, |
| 0:40.1 | I'm down if you are. And I'm like, of course, I would love to have you back. So I'm excited to see |
| 0:46.3 | where this conversation goes. I know that everybody's ears perked up as they heard about, |
| 0:53.0 | you know, a single guy in his 30s dating. |
| 0:55.8 | That's what they want to hear. So really excited to hear what's going on in your life. |
| 1:01.2 | Last time we talked was almost exactly a year ago. And you were talking about, you know, |
| 1:07.8 | feeling pretty good about being single, being, you know, super confident in who you were. |
| 1:14.0 | You had kind of just gone on this personal growth journey. |
| 1:16.4 | You learned how to like navigate singlehood in the way that worked for you. |
| 1:20.8 | Where do you stand on that today? |
| 1:23.7 | How are you feeling now? |
| 1:32.5 | Okay, so I finally picked up Dawn of Chaos and Fury by Melissa K. Rouric, and I need to talk about it because this series completely pulled me out of my |
| 1:37.5 | reading slump. It's one of those worlds that makes you fall back in love with reading. This is the |
| 1:43.2 | fourth and final book in the legacy series, |
| 1:45.2 | and what I love about it is that it is the perfect gateway romanticcy if you're not usually a |
... |
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