U Up?

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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Bob the Drag Queen and Jared kick off today’s episode bonding over their favorite WWF wrestlers and swapping stories from their early stand-up comedy days. Then they dive into modern dating drama, including a straight boyfriend who wants to explore drag, but his girlfriend is feeling insecure and unsure how to navigate it. They red flags, deal breakers, and quirky relationship moments, from mannequins at the front door to reality TV obsession. Bob talks about having two boyfriends and advises an emailer that dating an ENM man is a definite dealbreaker if you’re monogamous at heart! Along the way, Bob shares stories from Eddie Izzard, Harry Styles, Moulin Rouge, and life on stage.  It’s a fun episode you don’t want to miss, and be sure not to miss Bob on Broadway until March 22! 👉: https://www.bobthedragqueen.com/appearances
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Jordana is on maternity leave, so Jared Fried is joined by BETCHES’ Jack Maloney to break down a second date disaster featuring aggressive tongue, a “breast exam” style titty grab, and whether bad kissing is an ick or just picky. They share exact language to use in the moment like whispering “slow down” and how to reset physical chemistry on date three. Jared tackles a listener’s breakup after a layoff where an ex is telling people she only dated him for money, and he explains why the dumper is always painted as the villain and the one text to send. Plus, they answer a vulnerable email from a trans woman who feels invisible in dating and unpack how straight men think about attraction, fear, and identity.
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