It’s a Mailbag Monday on the JTrain Podcast! Jared is coming to you live from Des Moines, Iowa, where he’s soaking in the cozy, small-town vibes, indulging in breakfast adventures, and tapping into some new material. Jared shares some travel tales, thoughts on diners (Team Perkins vs. Cracker Barrel, anyone?), and why suggestions—even the unsolicited ones—can open new doors in your brain. Whether it’s a relationship dilemma, friendship faux pas, or an “Am I The A$$hole?” moment, Jared is here for you!

In this episode of the JTrain Podcast, Jared tackles two listener dilemmas that delve into the complexities of dating and communication. First, he responds to a letter from a woman grappling with rejection after disclosing her HSV status to someone she deeply connected with. Jared explores the challenges of breaking stigmas in dating, the importance of timing in vulnerable conversations, and how a partner’s reaction can reveal deeper incompatibilities.

Next, Jared unpacks a perplexing scenario from a listener who faced mixed signals while dating someone passionate about dance. From a rejected kiss to an awkward encounter at a music festival, Jared dissects the subtle cues and communication gaps that can derail a budding connection.

This episode is a thoughtful exploration of vulnerability, boundaries, and how to navigate dating’s many gray areas. Tune in for candid advice and practical takeaways for handling rejection, managing expectations, and understanding the signals we give and receive. Listen, laugh, and share with a friend who needs a dose of honest advice!

Email your questions to jtrainpodcast@gmail.com or DM the pod on Instagram @jtrainpodcast

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

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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

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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/