Jared is joined by original U Up? co-host Sami Sage for a fun episode that kicks off with body image, Ozempic shame, and why vulnerability isn’t owed, but it does matter. They unpack a listener’s dilemma about dating a woman who may have lost weight on GLP-1s and whether hiding old photos is a red flag, a boundary, or none of his business. Then they review texts from a guy who gives his date the ick by editing his messages multiple times, one edit should be the max! Sami and Jared also discuss what women should actually get men for the upcoming Valentine’s Day. Lastly, they dig into two red flag deal breakers: staying close with an ex-wife and being single at 33 – is that a red flag?

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Jared is joined by VP of BETCHES, Bryan Russell Smith, to kick off a Friday Feels episode that starts with a funny discussion about watching Heated Rivalry and why women are loving this show so much! Bryan shares how he met his now-husband at a bar after losing his coat, their age gap, and what Jared thinks straight dating could learn from gay dating honesty. They then dig into an icky or picky email where a listener gets dumped for loving Beyoncé, Taylor Swift, and Sabrina Carpenter instead of indie rock. Jared and Bryan answer a Valentine’s Day gift question, revealing why Valentine’s Day cookies aren’t just treats, but a way to show where someone really stands in a relationship. Finally, they answer a vulnerable email about disclosing STI on a first date, and if sharing an educational podcast is the way to go?

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Jared welcomes Vivian Tu (@your.richbff) as the first guest during Jordana’s maternity leave, and the conversation focuses on one of the most emotional topics in relationships: money. Vivian shares why she left Wall Street, how she became a personal finance creator, and why it is important to talk about money with your partner, even on date one. They tackle a real rent divide dilemma, breaking down how splitting costs “equally” can quietly build resentment when incomes are not the same, and why a fair, proportional split matters more. They unpack a prenup panic email, where a boyfriend wants a prenup because the government already has one on your marriage, making refusal to discuss one the real red flag. Vivian also drops a hard truth: a guy can be rich on paper, but if money is all he brings to the table, he is actually poor where it counts. Be sure to check out Vivian’s new book: ⁠Well Endowed⁠, out everywhere now!

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It’s Jordana’s last episode before maternity leave but you can still catch episode with Jordana on their latest Benefits episodes 👉 betches.com/podcast-channel/u-up/

J&J get into emails and break down a petty or prudent dilemma involving a $20,000 “gift” from a wealthy ex and whether keeping it after a breakup is fair game. Plus, an advice email sparks a heated conversation about saying “I love you,” with age gaps 24 vs. 37, and why not all “I love yous” mean the same thing!

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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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In this Friday Feels episode opens, Jared and Jordana get into Jared's very Florida Christmas and whether he really deserved getting called out for taking selfies in public. They dive into whether Happy New Year” is a criminally lazy dating-app opener, how late is too late to send it, and the exact moment “HNY” becomes unforgivable. Then, a listener questions whether her husband’s friends are genuinely uncomfortable or just chaotically harmless, and how much nonsense you’re actually expected to tolerate at the beginning of a relationship. Finally, J and J wonder if a listener should 'tolerate' or 'tap-out' – debating whether it’s worth pushing for a second date or if rejection is just the universe telling you it was never a match to begin with.

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