It's MAILBAG MONDAY! 💌 where he takes on emails, messages, and DMs from listeners seeking his unfiltered, honest perspective. His take? He’s not a therapist but offers something just as valuable: an unbiased take with no eye contact required! 

We learn first what is going on with Jared! He's diving into the complex feelings that come with trying to “make it” in a big city while balancing the small-town mentality. He reflects on chasing big dreams and the pressure to constantly grow, sharing his goal to make his next comedy special iconic, despite knowing Madison Square Garden might be a lofty ambition. For Jared, this high-stakes chase feels exhausting at times, especially compared to people who seem happy with simpler lives in small towns. The question arises: is striving for success making him happier, or is it just adding stress?

An email where they are looking for a job but annoying everyone about it! From a listener brings up classic feelings of being "left out" when visiting old friends who seem content in their local circles. Jared connects deeply with the listener’s high school-style anxieties about belonging, inclusion, and questioning their own life choices. He explains that even in adulthood, we never fully escape high school social dynamics—feeling left out or judged is universal. His advice? Reach out to these people again, enjoy the simplicity, and maybe embrace being the “new kid in town” as a fresh chapter rather than a source of insecurity.

As the episode wraps up, Jared highlights relatable issues like hating a day job while working toward a dream. He compares it to his own struggle with writing a book, where some days are rewarding and others are draining. His takeaway: it’s tough to keep going when fulfillment feels distant, but persistence might just lead to something great.

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/

🎙🚊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.

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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/