Episodes

  • He Fights Dirty With His Family—Will He With Me? ft Matteo Lane

    He Fights Dirty With His Family—Will He With Me? ft Matteo Lane
    Feb 18 2026
    Why is everyone obsessed with Heated Rivalry? Jared and his friend from the stand-up comedy world, Matteo Lane, kick things off by unpacking the hype around the viral hockey romance before diving into a chaotic round of red flag or dealbreaker. They debate whether a boyfriend kissing his girlfriend every single time she gets in the car is romantic or suffocating, react to the shock of a surprise giant tongue ring mid-dating, and argue over a man who feels “betrayed” after learning his girlfriend had a nose job at 19. The episode spirals into celebrity look-alike delusion (strong Joey Tribbiani energy), plus why everyone can’t stop talking about The Golden Bachelor! It's a modern dating drama, cosmetic surgery disclosure debates, and maybe too brutally honest relationship takes! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 17 mins
  • Why Dating Feels So Negative Right Now ft. Matchmaker Maria

    Why Dating Feels So Negative Right Now ft. Matchmaker Maria
    Feb 13 2026
    Is celebrating Valentine’s Day a basic expectation, or optional? Jared and Matchmaker Maria unpack a petty or prudent situation where a woman uses an entire couples spa gift card on herself after her boyfriend refuses to acknowledge Valentine’s Day at all. J & MM break down how attitude is everything in dating and why showing up authentically matters, especially for Gen Z. They also share what to do if you’ve been seeing someone for one day versus a few months for Valentine’s Day. Then, a listener asks how to tell a guy she wants to wait to have sex, without killing attraction, right before their first Valentine’s Day together. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    53 mins
  • When Body Image Becomes a Dating Issue ft. Sami Sage - Co Founder of Betches

    When Body Image Becomes a Dating Issue ft. Sami Sage - Co Founder of Betches
    Feb 11 2026
    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? Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 26 mins
  • He Dumped Me Because Of My Music Taste?!

    He Dumped Me Because Of My Music Taste?!
    Feb 6 2026
    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? Learn more about your ad choices. Visit megaphone.fm/adchoices
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    52 mins
  • Why Money Conversations Matter Early in Dating ft Vivian Tu

    Why Money Conversations Matter Early in Dating ft Vivian Tu
    Feb 4 2026
    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! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr
  • He’s 24, I’m 37 - Can We Really Be In Love?

    He’s 24, I’m 37 - Can We Really Be In Love?
    Jan 30 2026
    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! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    39 mins
  • I Can’t Stop Comparing Myself to His Ex!

    I Can’t Stop Comparing Myself to His Ex!
    Jan 28 2026
    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! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    1 hr and 10 mins
  • Coming Out After Kids ft Chris Appleton

    Coming Out After Kids ft Chris Appleton
    Jan 23 2026
    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! Learn more about your ad choices. Visit megaphone.fm/adchoices
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    43 mins