It’s a hilarious and heartfelt Chit Chat Wednesday as Jared Freid sits down with comedian Eric Neumann, fresh off the release of his brand-new YouTube special, Almost Engaged. Together, they dive deep into the emotional rollercoaster of love, heartbreak, and the comedy that comes from it all.

Eric opens up about his not-quite engagement and the real-life relationship that inspired the special, including his brother’s chaotic divorce and the now-infamous couch painting that came with it. The two comics explore the tricky process of turning personal pain into punchlines, the healing power of yoga, and why post-breakup dating is its own kind of trauma response. Jared shares his experiences with joke-building after a breakup, the moments that still make him cringe (including the coffee bit that got him on The Tonight Show), and how to know when it’s time to let go of material and people.

From the origin story of “Napkin Neumann” at the Comedy Cellar to a deep discussion on vulnerability, timing, and growing past heartbreak, this episode is packed with honesty, laughter, and insight into how comedians turn real-life chaos into cathartic comedy.

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🙋🏻‍♂️ Jared Freid

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Website - https://jaredfreid.com/

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🙋‍♀️ Our Producer Venetia AKA V

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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 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/