It's CHIT CHAT WEDNESDAY!! 🙌 Jared Freid is joined by the always sharp and hilariously insightful Michelle Wolf this week. The two comedians dive into a range of topics, from the changing New York weather to the complexities of modern content creation and comedy in a podcast-saturated world. Jared and Michelle pull back the curtain on their frustrations with low-effort content, while also sharing their own challenges in maintaining authenticity in comedy amidst evolving trends.

Michelle, fresh off launching her new podcast Thought Box, gives listeners a sneak peek into her process of embracing (and sometimes hating) the world of podcasting. Jared and Michelle banter about the absurdity of everyday life and the fine line between comedic inspiration and chaos, while poking fun at their own creative processes. They share candid moments about their evolving careers, the importance of refining jokes, and the pressure to stay true to their craft in a world where everyone seems to have a podcast.

A major theme in this episode is the generational shift in technology and communication. Both Jared and Michelle reflect on being part of the last generation to grow up without constant connectivity, diving into the humorous challenges this creates with their parents. Jared’s story about his mom’s “loving bullying”—turning simple questions about doctor visits into guilt-inducing traps—is both relatable and hilarious. Michelle adds her own insights on how parents, with their seemingly innate guilt-tripping abilities, can twist even well-meaning compliments into self-inflicted emotional spirals. Jared goes so far as to label his mom a "guilt kung fu master," turning everyday conversations into mini guilt-marathons.

As the conversation turns to parenthood, Michelle reflects on the unexpected compromises that come with raising kids. She shares how her eco-friendly ideals often take a backseat to the practicality of disposable paper plates and spontaneous zoo trips, providing a funny yet real glimpse into the balance between convenience and morality. Michelle hilariously explains her newfound appreciation for strollers—“the best rolling pockets”—as she navigates the chaos of parenthood and everyday life.

Throughout the episode, Michelle talks about how these personal experiences with family, guilt, and the mundane aspects of life fuel her comedy. they dive deep into the endless cycle of guilt, parental struggles, and the world of comedy. Jared talks about how his mom is the best at guilt tripping him. How his mom is some sort of “guilt kung fu masters,” able to turn any well-meaning compliment into a situation where you’re suddenly tapping out from a self-inflicted punch! 😂

The episode wraps up with Jared and Michelle discussing the ever-evolving comedy scene, sharing their frustrations, joys, and the occasional absurdity of staying relevant in a world dominated by content creators. With sharp observations, witty banter, and laugh-out-loud moments, this episode offers a deep dive into the intersection of comedy, guilt, parenthood, and personal convenience—all delivered with the signature humor of two comedic heavyweights.

Tune in for all this and more, including a shout-out to all of you writing in! continue to write in at 👉jtrainpodcast@gmail.com or DM us at @jtrainpodcast

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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 jtrainpodcast@gmail.com – 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/