Do I Have To Invite My Boss To My Wedding? - MONDAY MAILBAG
The JTrain Podcast
Jared Freid
4.8 • 4.8K Ratings
🗓️ 29 September 2025
⏱️ 41 minutes
🧾️ Download transcript
Summary
It’s Mailbag Monday! And Jared dives into a work-themed episode with listener questions that blur the lines between business and personal boundaries. From a coworker crush that could complicate a promotion, to flirty banter that wasn’t so friendly, to the awkward pressure of inviting your boss to a wedding, no dilemma is off-limits. Jared breaks down how to handle workplace relationships, tricky guest lists, and the risks of mixing romance with your career!
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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. |
| 0:12.4 | It's a mailbag munder. |
| 0:20.8 | Hello and welcome to the J-Train podcast. |
| 0:24.5 | This is J-Train, Jared Freed coming you live from Del Rey Beach, Florida. |
| 0:30.3 | That's right. |
| 0:31.4 | Every Monday, it is a mail-bag Monday where you, the listener, email me, the comedian with your advice questions. |
| 0:41.5 | I've been doing advice podcasts for 13 years. 13 years. So I guess my experience leads me to being, I think, I would hope better at dissecting the email, |
| 0:59.4 | finding the interesting part of the email and also giving you an unbiased response to whatever |
| 1:05.9 | you're going through. |
| 1:06.9 | Today, our producer V has put together a theme week. It is work themed. And who better to |
| 1:15.4 | ask your work questions than a guy that hasn't been in an office in 15 years. But I will say |
| 1:24.7 | this is an entrepreneurial endeavor I'm doing. I and yeah, it's, this is, |
| 1:32.0 | you might be like, ah, you know, funny clown guy, you make your jokes and you have your fun and |
| 1:36.9 | you, you dance on stage and you, you make your funnies and it's, uh, all fun and games. No, |
| 1:43.2 | this is a business. |
| 1:44.8 | That's right. |
| 1:46.1 | I would love to go on Shark Tank and like, |
| 1:49.3 | I want to like present 10% of me, |
| 1:53.7 | Jared Free, the comedian. |
| 1:55.2 | I always wondered, |
... |
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