The JTrain Podcast

Author: Jared Freid

The JTrain Podcast is hosted by comic Jared Freid and great comedian guests as they read listener emails and answer questions about everything from hooking up and dating apps to relationships and post-grad problems. Every Monday!
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Language: en

Genres: Comedy, Comedy Interviews, Health & Fitness, Sexuality

Contact email: Get it

Feed URL: Get it

iTunes ID: Get it

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How Do I Get a Guy to Ask Me Questions on a Date?! - MONDAY MAILBAG
Sunday, 22 February, 2026

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.comCheck out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy FriendSupport 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