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The JTrain Podcast

Do I Keep Dating A Really Nice Guy? - MONDAY MAILBAG

The JTrain Podcast

Jared Freid

Comedy Interviews, Comedy, Health & Fitness, Sexuality

4.84.8K Ratings

🗓️ 12 January 2026

⏱️ 36 minutes

🧾️ Download transcript

Summary

Jared opens Mailbag Monday from Delray with gratitude, beach energy, and a reminder that anonymous advice hits harder than biased friends. The standout email comes from a listener who went on six “pretty good” dates and can’t stop thinking about bunny-rabbit sex, being asked to fetch latkes, and having to share a single hot dog at a hockey game. Jared’s verdict is clear and funny: if it’s still only “pretty good” after six dates, that’s already your answer. He reframes dating like investing, asking whether this relationship could realistically get 10 percent better and become a life you actually want. The lesson is not that she’s too picky, but that chemistry matters more than politeness and settling only builds resentment. Classic JTrain delivers a warm hug, a reality check, and permission to move on without guilt!


 

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend


Get $2.99 per meal on your first box & free steak for a month with code JTRAINSTEAK at http://everyplate.com/podcast  

Transcript

Click on a timestamp to play from that location

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.

0:15.5

It's a mailbag Monday.

0:20.9

Hello and welcome to the J-Train podcast.

0:23.3

It's a J-Train, Jared Fried.

0:24.3

Coming you live from Delray Beach, Florida.

0:27.7

That's right.

0:28.8

Every Monday is a mail-bag Monday where you, the listener, email me, the comedian, with your questions, anything you'd like.

0:36.3

You can send in anything you like friendship questions

0:40.7

relationship questions anything family anything that's like a real specific story that you want to

0:50.8

hear the feedback from someone who doesn't know you, where you can be anonymous,

0:55.8

so you can hear an honest answer. That's the problem with advice from friends. They know you and

1:00.5

they have already built all of their biases. Is it biases or biases? Whatever it is, they know you

1:08.1

from college and they go, well, you got drunk that one time. So you're

1:11.6

probably doing this or that. I come here just with what you write to me in the email and I'm

1:17.5

going to give you a perspective. It's going to be honest. It's going to be thoughtful. It's going to be

1:21.5

kind. It's also going to be real. I hate those people. I'm going to be real. I, you know,

1:27.4

I'm not saying as a brat.

1:28.6

Anyone would.

1:29.8

It's easier here from my computer at the beach, baby.

1:35.2

Listen, want to thank you for being a listener.

...

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