IT'S MAILBAG MONDAY! In this week’s Mailbag Monday episode of the JTrain Podcast, Jared Freid takes on 2 listener dilemmas, diving into the tricky situation of whether or not to tell a close friend their new boyfriend is bad news.👎 He discusses the challenges of navigating friendships when romantic relationships are involved and gives his signature no-nonsense advice.

Jared also reflects on the evolving podcast landscape, sharing his thoughts on the pressure to feature big-name guests versus his preference for creating authentic, relatable content for his dedicated listeners. Throughout the episode, he touches on hilarious and relatable topics, such as the awkwardness of seeing your ex with someone new—whether they’ve upgraded or downgraded—The discussion starts with a listener sharing her feelings about an ex-boyfriend she had dated for two and a half years in their late 30s. She explains how she ended the relationship because he couldn’t commit, which felt like being forced to break up with herself. Even though she's over him, she admits to checking his Facebook occasionally, and a friend recently got upset on her behalf after seeing a picture of him with a new girlfriend. Her initial reaction was to feel an ego boost, thinking the new girlfriend was a downgrade.

Jared acknowledges that it's common to feel validated when an ex "downgrades" but challenges this mindset as unhealthy. He encourages a shift in perspective, reminding the listener that the relationship ended because they weren’t a good match, and it’s pointless to compare. The new relationship could be fulfilling for reasons beyond appearances, and it’s impossible to know what dynamic works for the new couple. Using a “buttoned-up shirt” analogy, Jared suggests that unresolved issues can weigh down a relationship, and the ex might have moved on to start fresh. He adds that fixating on whether an ex has "upgraded" or "downgraded" isn’t productive and could mean the listener hasn’t fully moved on. Jared emphasizes that true healing comes from focusing on personal growth rather than seeking validation through comparisons.

Tune in for all this and more, including a shout-out to all of you writing in! continue to write in at 👉[email protected] or DM us at @jtrainpodcast

GreenChef 👉 Support the show and get 50% off your 1 st GreenChef box, plus 50 free ClassPass credits. Use code JTRAINCLASS at https://www.greenchef.com/JTRAINCLASS

BetterHelp 👉 This episode is sponsored by BetterHelp. Give online therapy a try & get on your way to being your best self at https://www.betterhelp.com/JTRAIN

MeUndies 👉 Support the show and get 20% off your 1 st MeUndies order, plus free shipping. Head to https://MeUndies.com/feather

🙋🏻‍♂️ 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/