Jared kicks off this Mailbag Monday with a listener who’s ready to see the world! But her friends are stuck in life stages that make travel impossible. Should she go solo, join a travel group, or keep waiting for a plus-one? Jared shares personal insights from his own travels, tackling the guilt and self-doubt that come with booking a trip alone.

Then, we dive into a complicated relationship dilemma from a self-proclaimed “40-year-old cradle robber” dating a younger man with overbearing parents. His dad’s disapproval and outdated timeline for marriage and kids are casting a shadow over their future. Jared breaks down the pressure, the power dynamics, and whether it’s possible to build a life together without parental support! This listener actually has a couple more problems than she thinks!

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🙋🏻‍♂️ Jared Freid

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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 [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/