It's Monday which means Jared has a Mailbag Monday for you! This week, he’s tackling two heavy-hitting topics: “I’m Having an Emotional Affair with My Neighbor” and “2 Weddings on the Same Day.” These stories promise a captivating mix of high-stakes drama, questions, and scenarios that feel all too relatable. There's a lot of tension of an emotional affair, exploring where the line blurs between friendship and something more, especially when unspoken feelings and close proximity come into play. Meanwhile, the “Two Weddings on the Same Day” dilemma brings up all the chaos, stress, and tactical planning that come with wedding season, as Jared advises on managing conflicting commitments without losing friends — or sanity.

The episode dives even deeper as Jared discusses the complexities of dating confidence, particularly when it involves age gaps and mismatched emotional availability. A listener writes in about her ongoing frustrations with a man who emotionally engages her, despite recently dating a much younger woman. Jared tackles the psychology behind this pattern, pointing out that some men may seek “easier” relationships—where fewer intense conversations and future expectations mean they can dodge vulnerability and emotional exposure.

Jared thoughtfully unpacks why relationships with women in their 30s or 40s often bring a maturity that demands honesty and depth. He suggests that the listener’s age is far from the issue; rather, her date’s hesitation likely stems from his own insecurities. Dating a peer requires stepping up to accountability and commitment, and Jared emphasizes that a partner worth her time will value these qualities, not avoid them. His advice is clear and actionable: she should focus on conserving her emotional energy, setting clear boundaries, and putting her needs first. By focusing on someone who appreciates her strengths and authenticity, she can make space for a relationship that thrives on mutual respect and admiration.

Tune in to this week’s Mailbag Monday for candid advice, relatable anecdotes, and the laughs you can only get from Jared Freid’s sharp and compassionate takes on modern dating! Plus, don’t forget to submit your own questions for a chance to hear them answered on an upcoming episode.

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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/