U Up?

Comedian Ashley Gavin joins Jared to talk about dating, sexuality, and the chaos of life on the road! Ashley explains her open relationship rules with her girlfriend, their monthly check-ins, and how touring sometimes leads to unexpected hookups. They tackle listener emails about bisexual curiosity blowing up a relationship and whether a 35 year old with a roommate should be a concern? Plus, Ashley shares what life on the road is really like, from asking a hookup to put her knife away to fans having unexpected coming-out moments at her shows. It’s a fun episode where we learn all about the Gavin Method!!
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Jared is joined by Hinge relationship expert, Logan Ury, to break down some of the biggest dating questions listeners are dealing with right now. They debate whether asking for a voice note before a first date is an innocent preference or a major red flag, and unpack the idea of “digital body language” when someone is great in person but disappears over text. They also dive into the classic “right person, wrong time” debate and the Sex and the City taxi-light theory of commitment. Also, one listener wonders if dating in NYC has become impossible thanks to hyper optimized schedules full of cold plunges, pilates, and skincare routines. Is it selfish or self care?
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Jared is joined by BETCHES’ own Tess Tregellas for a hilarious Friday Feels episode. Tess shows up with a positive attitude but she does reveal she just learned sad news about her childhood dog. But quickly turns the mood around as they dive into listener dilemmas! They debate whether calling your fiancée a “solid 8 out of 10” is a red flag or a relationship killer, and explore why words like “pulchritudinous” are far superior to numbers when describing your partner. Later, the two help a listener spiraling about moving in with her boyfriend in NYC, covering anxiety, overthinking, and why sometimes you just have to be excited about love! Plus, Tess shares the wild story of meeting her boyfriend while wearing a wedding dress!
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This week on U Up?, Jared is joined by Aleen Dreksler, CEO and co-founder of BETCHES, for a chaotic and honest deep dive into mama drama, ex etiquette, and career vs. kids debates. They discuss boundaries with mother-in-laws and what you can negotiate versus when you should just say nope, covering everything from holiday turf wars to posting your baby on Instagram without permission. Then it’s petty or prudent when an ex crashes a run club and sends a seriously annoying “it’ll get easier over time” text. Plus, an Icky or Picky ruling on a second date who announces a strict “no phones at the table” policy like he’s running a dictatorship. Be sure to not miss updates from Jordana! 👉 https://subscribe.betches.com/u-up-with-benefits
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Jared is joined by Dr. Naomi Bernstein of the Oversharing podcast to unpack dating after divorce, performance anxiety, and whether taking intimacy slow signals emotional baggage. They break down an email from a 34-year-old woman dating a gentle, recently divorced man who says something “deeper than biology” is blocking intimacy. Then they debate if a flight attendant was right to tell a 30-year-old guy he’s “too nice for casual dating.” Plus: performance anxiety, people pleasers, alpha vs beta energy, and why sexual chemistry doesn’t always match long-term potential. Jared and Dr. Naomi get deep and at one point, when Jared asks Dr. Naomi to give him real advice about his own dating life!
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