In this week’s Mailbag Mondays, host Jared dives into two emotionally charged listener dilemmas that demand his signature blend of humor and honesty. From virtual betrayals to mixed signals in the workplace, Jared is here to break it all down.

First up, a listener grapples with the aftermath of discovering her husband’s emotional affair in the virtual reality world. After learning about the betrayal—complete with screen grabs and “I love you” messages—she’s left questioning everything about their marriage. Jared shares thoughtful advice on rebuilding trust, navigating marriage counseling, and figuring out how to stop the obsessive cycle of re-checking and replaying. Can their relationship survive this digital heartache?

Then, it’s a tale of workplace flirtation gone cold. A listener met a guy at her job just as he was leaving, took a bold shot in his DMs, and got... an ambiguous response. Is she reading too much into it? Should she shoot her shot one more time or let it go? Jared dissects the psychology of social media follow-backs, modern dating ambiguity, and why some guys just can’t commit to grabbing a drink.

Whether it’s navigating marriage post-betrayal or decoding the maddening mind games of dating apps, this episode is packed with Jared’s no-nonsense advice for anyone trying to make sense of modern love. Don’t miss it!

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

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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 [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/