Going On A Date With An Old Hookup, How Do I Make It Real This Time? - MONDAY MAILBAG
The JTrain Podcast
Jared Freid
4.8 • 4.8K Ratings
🗓️ 20 April 2026
⏱️ 43 minutes
🧾️ Download transcript
Summary
It’s Mailbag Monday, and Jared is giving advice on 👇
- Am I ruining the romance by not letting him fully handle and pay for the proposal?
- Reconnecting with a past hookup on Hinge, but I want it to be serious this time
- Boyfriend in a wild sports group chat called the “Titty Committee” - ew
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Transcript
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| 0:00.0 | It's a mailbag munder. |
| 0:03.3 | You've got problems there. |
| 0:07.3 | I'm going to help you from the comfort of my chair. |
| 0:15.1 | It's a mailbag Monday. |
| 0:20.7 | Hello and welcome to the J-Train podcast |
| 0:24.1 | This is J-Train Jared Freed coming you live |
| 0:27.1 | from Delray Beach, Florida. |
| 0:29.6 | That's right. |
| 0:30.6 | Every Monday is a mailbag Monday |
| 0:33.9 | where you, the listener, email me the comedian with your questions and I did do a call |
| 0:40.7 | to action last week for more questions we always need more questions we want them to be real |
| 0:49.1 | thoughtful thorough we want real issues friendship issues issues, relationship issues, family issues, |
| 0:55.3 | whatever you're going through. Just send it to J-Train Podcast at gmail.com. J-Train Podcasts at |
| 1:01.8 | gmail.com. And the one thing about you guys as a listenership, when I ask, you listen, |
| 1:09.3 | and I really do appreciate it because I have three emails |
| 1:12.8 | in front of me that are thorough. I don't read them before. I like to read them with you, |
| 1:19.4 | the listener. I want you to get my, you know, my immediate take on your issue. This is a conversation. |
| 1:27.2 | So there are three thorough emails. |
| 1:29.9 | I'm going to ask you if there's something we talk about today that you think would be interesting |
| 1:35.2 | to the group chat, that you want to hear other people hash out, send this episode to the friend |
| 1:41.9 | group, the family, whoever you group chat with, send it. |
| 1:45.7 | Or just someone that you just, you might have been talking about this exact thing that we go |
... |
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