This week on Mailbag Monday, Jared kicks off the show with a trigger warning for listeners, as one of the emails touches on sensitive topics related to pregnancy and abortion. If that’s something you’d prefer to avoid, feel free to skip the second email of today’s episode.

As always, Jared dives headfirst into your dating dilemmas with his signature mix of humor and honest perspective. First, he reflects on why people trust him with their deepest questions—because he’s been offering unfiltered advice for over a decade! Unlike your friends and family, Jared won’t soften the truth just to avoid an awkward moment.

A listener is stuck trying to navigate the tricky “intentions conversation” with a guy she’s been dating for a few months. Is he as interested as she hopes, or is she overanalyzing his behavior? Jared breaks down how to take control of your dating narrative and stop playing detective.

In the second email, a complex situation involving pregnancy has Jared offering compassionate yet straightforward advice on how to approach difficult conversations with a partner. After a whirlwind romance leads to an unplanned pregnancy, our listener moves in with her boyfriend only to stumble upon a heartfelt letter he wrote to his ex—a week before they met. Now, she’s grappling with insecurities about their timeline, unspoken truths, and whether she’s truly his "person."

Jared unpacks the situation with his signature humor and insight, exploring topics like post-breakup loneliness, boundaries with exes, and why clear communication matters more than detective work. Plus, he shares practical advice for addressing uncomfortable truths in a relationship without losing your sense of self.

Throughout the episode, Jared also touches on his recent experiences in Tulsa, the highs and lows of performing live shows, and how he balances career anxieties with staying grounded. Plus, he shares exciting updates on upcoming shows in Dania Beach, Portland, Phoenix, and even Australia and New Zealand!

Don’t forget to support the show by sharing it with friends, following on Instagram, or subscribing to Jared’s Patreon for exclusive weekly content like “Coffee with JTrain,” where he gives a raw and unfiltered look into his life. Don't miss this rollercoaster of emotions, revelations, and Jared’s candid take on modern dating dynamics!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Lumen Support the show and get 15% off your Lumen. Head to https://www.lumen.me/JTRAIN

Hero BreadSupport the show and get 10% off your order of Hero Bread’s new recipe. Use code JTRAIN at https://www.hero.co

🙋🏻‍♂️ Jared Freid

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

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

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

🙋‍♀️ 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 and 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 to awkward setups to 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/