This week’s Mailbag Monday brings two wild listener stories that’ll have you shaking your head and laughing out loud. First, Jared responds to a med school listener whose whirlwind romance with the class clown took a sharp turn into weirdsville. From bizarre family dynamics involving a touchy sibling to a jaw-dropping white coat ceremony reveal, this story is packed with twists, including a moment that made her walk out for good. But now that she's trying to stay civil, friends say she's being too nice—what should she do?

Next up, a listener seeks advice on some late-night Instagram behavior from her friend’s husband. Picture this: 2 AM likes on photos dating back to 2019… and then another spree at 4 AM, this time digging all the way to 2016. Is this classic "tap the glass" flirting? Should she tell the wife, confront him, or steer clear entirely? Jared breaks it all down with thoughtful advice, sharp humor, and insights you won’t want to miss.

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🙋🏻‍♂️ Jared Freid

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Twitter - https://twitter.com/jtrain56

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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 [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/