My lifelong friend flirted with me!! What now? - MONDAY MAILBAG - The JTrain Podcast w Jared Freid

Jared is coming to you from Australia, sharing hilarious stories and insights from his travels abroad — from navigating local customs, wine tours, zoos, to discovering the best spots to grab a bite. But even oceans away, the emails keep coming!

First up, a listener writes in about a drunken night swim with a lifelong friend at her family’s lake house. Despite innocent intentions, her husband is still upset months later and wants to confront the friend. Jared unpacks the tricky balance between trust, boundaries, and marriage dynamics.

Then, another listener is feeling the pressure of mismatched timelines. She’s 31, her boyfriend is 41, and while she’s ready to move in and talk kids, he’s still unsure. Jared breaks down how to navigate a relationship when your life plans don’t quite align.

Tune in for thoughtful advice, candid takes, and a little Aussie flair. The Lounge is open — let’s get into it!

Support the podcast by supporting our sponsors!

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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/

🎙🚊Follow JTrain Podcast

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

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

🙋‍♀️ 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/