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The JTrain Podcast

How Do I Get a Guy to Ask Me Questions on a Date?! - MONDAY MAILBAG

The JTrain Podcast

Jared Freid

Comedy, Sexuality, Health & Fitness, Comedy Interviews

4.84.8K Ratings

🗓️ 23 February 2026

⏱️ 42 minutes

🧾️ Download transcript

Summary

On today’s Mailbag Monday, Jared covers 3 modern dating dilemmas: how to shut down a mother in law calling you “mama” without starting family drama, whether seeing bikini models on a guy’s IG Explore page plus multiple dating apps is just normal dating or a real red flag, and what it means when someone asks about your day but never follows up. Is it a lack of emotional curiosity or just bad conversational skills? Jared breaks it all down!

Jared is on tour! 👉 jaredfreid.com

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


Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co 

Support the show & get 20% off your Joymode order with code JTRAIN at http://TryJoymode.com/JTRAIN 

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.

0:15.1

It's a mailbag Monday.

0:20.8

Hello and welcome to the J-Train podcast.

0:23.8

This is J-Train Jared Freed.

0:25.1

I'm from Delray Beach, Florida.

0:28.0

That's right.

0:28.5

Every Monday is a mailbag Monday.

0:31.9

We're me, the comedian, gets emails from you, the listener,

0:36.0

and I give you some advice, some perspective.

0:39.4

Why me?

0:40.1

If you're new here, I want to thank you for giving this podcast a shot.

0:44.9

If you've been here a while, I want to thank you for being a part of this show.

0:49.2

This is a mom and pop organization.

0:53.0

This is the J-Train Cinematic Universe. We are a daily show Monday through

0:58.1

Friday. Every day is a different theme if you join me because you saw an Instagram story that

1:05.1

piqued your interest or you saw a clip. That means something worked. And I'm excited to have you here.

1:10.7

I'm going to put on a show for you

1:12.1

and i want you to subscribe so that this podcast is here for you when you need it i have three

1:19.2

listener emails real people real problems why do they ask me because they've come to trust me over the years. I've been giving advice on the podcast, you know, forum for 14 years. That's right. And I think what I bring to the table is I'm going to be, I'm going to admit to all my biases as I answer the question. I'm going to be honest with you. And I'm going to try and be funny while doing it. But I used to say this when I would have guests on the advice version of this show, which, you know, we could do that again. That could happen again. I would say to the guests, I'd be like, listen, take the person

2:01.0

seriously. That's the first thing you have to do is take the email seriously. I don't care how

...

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