Happy (almost) New Year from sunny Boca Raton! 🌴🎉 Jared Freid is kicking off 2025 with a brand-new Mailbag Monday, answering two incredible listener dilemmas that embody everything the JTrain Podcast is all about—honest advice, tough love, and plenty of laughs.

First, we meet a listener who booked a 3 week European vacation with her boyfriend of just 4 months. But now she’s having serious second thoughts about their long-term compatibility. With the trip fully paid for by him, she’s torn about whether to go, how to handle the breakup if it happens, and what trip lengths make sense for new relationships. Jared dives deep, offering insights on travel, timing, and when it’s time to move on versus sticking it out.

Next, it’s a group chat disaster for the ages! A voice memo intended for a bestie lands in the “birthday weekend cabin trip” group chat instead, spilling the tea on the birthday girl’s friends and the weekend plans. The fallout? The group chat implodes, the trip is canceled, and now the listener is left wondering how to repair her best friend’s birthday and their relationship. Jared breaks down the best strategies to rebuild trust, whether to go heartfelt or funny with the apology, and why group chat etiquette should never involve long voice memos.

Along the way, Jared shares updates about his upcoming comedy tour (hello, Portland, Phoenix, and Australia!), what makes the JTrain Podcast a no-days-off operation, and why his perspective on dating and friendships remains unmatched!!

This episode is packed with thoughtful advice, hilarious commentary, and Jared’s signature style of tackling tough topics with care. Whether you’re navigating relationship doubts, friendship drama, or just need a laugh, this episode has something for everyone.

Email your favorite stories to [email protected] or DM the pod on Instagram @jtrainpodcast

🎙 Upcoming Shows: Portland, Phoenix, and more! Don’t miss Jared live—grab your tickets now.

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

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🙋🏻‍♂️ Jared Freid

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

Twitter - https://twitter.com/jtrain56

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

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.

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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/