How do I get a guy to ask me questions on the date? - MONDAY MAILBAG - The JTrain Podcast w Jared Freid

The JTrain Podcast

Jared Freid

Comedy Interviews, Comedy, Health & Fitness, Sexuality

4.8 • 4.7K Ratings

🗓️ 26 May 2025

⏱️ 32 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

This week, Jared dives into your burning dating dilemmas and keeps it real with his signature humor and insight. Also! Happy Monday and Memorial Day! Summer’s officially here, so let’s kick it off right with some juicy Mailbag Monday questions. First up: A listener’s stuck in a long-term FWB situation with a piano-playing guy who’s mysteriously hesitant to perform. Is he shy? Is it nerves? Jared weighs in on how to creatively nudge a reluctant musician without killing the vibe.

Then, Jared tackles the dreaded one-drink first date where the conversation is all about him—and none about her. Why do guys miss the memo that a good convo should be a ping-pong match, not a solo tetherball game? Jared shares his advice for spotting red flags and how men can show genuine interest!

Tune in for laughs, real talk, and Jared’s no-BS advice to help you navigate dating this summer.

Support the podcast by supporting our sponsors!

Get 20% off your first Caldera Lab order. Use code JTRAIN at https://www.calderalab.com/JTRAIN

🙋🏻‍♂️ Jared Freid

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Twitter - https://twitter.com/jtrain56

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Website - https://jaredfreid.com/

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🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

Jared Freid is a stand-up comedian from Boston who is currently based in New York City. Jared is known to give great dating advice and is all-knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations, awkward setups, and breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

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 monday.
0:25.5	Hello and welcome to the J-Train this is j train jared freet coming you live from the west village of manhattan that's right every monday it is a
0:32.2	mailbag monday where you the listener send in your emails, and I, the podcaster, comedian, and friend.
0:40.8	Give you some perspective, some advice, some thoughts.
0:44.1	And who am I?
0:45.2	I'm just a guy in a studio apartment looking at you, a person, a listener to a podcast.
0:56.1	That's all I am.
0:57.3	I'm just, I'm just, just a friend, a friendly voice who doesn't have to make eye
1:02.8	contact with you.
1:03.6	That's a big part of this, that I don't have to like, I don't have this worn in relationship
1:08.8	with you where I have to be afraid of saying what I really feel to
1:12.9	you. So that's why I'm asking you the listener. If you're going through something, send it in.
1:19.7	J-Train Podcast at gmail.com. That's J-Train Podcast at gmail.com. It's not ticked off Tuesday, so I was about to have a complaint.
1:30.1	I'm not going to do it.
1:30.9	I'll do it tomorrow.
1:32.1	I'll do it tomorrow.
1:33.5	We'll do it tomorrow.
1:35.9	If you're out there and want to come to a show, Pittsburgh, London, assemble the group
1:43.5	chat.
	...

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