This week's Mailbag Monday has it all! Workplace hookups, marriage drama, and unwanted attention at dinner parties. Jared dives into a spicy email from a listener who hooked up with a coworker on a business trip, oh, and they're both married with kids! What started as flirtation turned into a secret connection, but now she’s wondering if he’s in it for more than just sex… or if it was just a convenient escape from their strained marriages. Is it an affair of the heart—or just office temptation taken too far?

Then, a wildlife biologist writes in with a different kind of conundrum: how to not become the center of attention in social settings when your job is cooler than everyone else’s. Jared shares advice on navigating curiosity without sounding like you’re bragging or auditioning for a TED Talk.

Whether you’re stuck between HR and a hard place or just trying to avoid oversharing at happy hour, this episode is full of honest insights and hilarious perspective.

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🙋🏻‍♂️ Jared Freid

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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/