U Up?

Jordana is getting ready to have her twiblings, and she and Jared talk about childhood memories and how they were raised! Then they jump into emails, starting with a listener in an ethically non-monogamous relationship wondering if she accidentally sent a hookup coded message when setting up a first date. Next, they offer thoughtful advice on when and how to bring up losing a family member while dating without scaring someone off. Then they dive into an icky or picky where a listener’s boyfriend spits loogies and snot rockets on walks, is it just “man behavior” or a real turnoff? Lastly, J&J get into red flag or dealbreaker, covering dating a great guy with a kid and a difficult ex, partners who speed through 2- to 4-month relationships, and a date who picks up their plate and licks off what’s left at the end of a meal!
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J&J are joined by celebrity hairstylist Chris Appleton, known for styling Jennifer Lopez and Kim Kardashian, to talk about hair, confidence and dating as a dad of two. Chris explains how hair can empower you, help you see yourself clearly, and change how you show up in dating and life. He opens up about his past relationship with a woman, raising children together, and navigating marriage and divorce in the public eye. Chris also shares how discovering his sexuality later in life helped him gain a deeper understanding of himself. Lastly, J&J and Chris answer a listener's question about an open relationship that’s getting difficult because one person caught feelings! Be sure to check out this episode and Chris’ new book Your Roots Don’t Define You, out now!
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J&J touch on the Ashley Tisdale friend-group drama and how being quietly dropped by friends feels a lot like modern dating, where things just fade out instead of ending with an honest conversation. J&J dive into listener emails, starting with a listener wondering if dating someone with zero social media in 2026 is normal or a red flag? They debate a messy breakup dog custody case in a classic petty or prudent, breaking down responsibility, fairness, and post-breakup guilt. Advice continues with how to deal with single friends who complain about dating but refuse to actually go on dates?! They end the episode with some fun red flag or dealbreaker about eating fries with a fork, to splitting a pricey bottle of wine and giving big birthday gifts too early.
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Jared’s making new friends in Florida-until a toe gets a little too friendly with his knee, sparking suspicions that one new pal might be part of a swingers couple. J&J dive into a first-date email from a woman whose date keeps a solo, youthful photo of his mom as his iPhone lock screen - sweet, or deeply unsettling? Next, they tackle a listener question about navigating the ticking biological clock on dating apps and whether it’s fair game to talk kids on a first date.
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J&J dive into New Year’s resolutions and float the idea that partners should choose each other’s goals, mostly because Jordana would like to veto Mike’s marathon plans. They get into listener emails, including one from a woman confused about being instantly unmatched for not sharing her number, and Jared explains why jumping straight to “Can I text you?” can backfire. In Petty or Prudent, a listener wonders if she may have crossed a line after throwing a situationship’s forgotten car key into Lake Ontario. Oops! Inspired by Tell Me Lies season 3, Jared and Jordana debate a Red Flag or Dealbreaker where a man performs a song about his ex—while his new girlfriend watches from the crowd. They also unpack a nine-year on-and-off relationship that ends in an engagement ultimatum, and what it all says about boundaries, timing, and whether a relationship is actually right for you.
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