It’s time for our anniversary Sunday Special, and this year is extra special because it marks 500 episodes of the U Up? Podcast! J&J are back in the studio celebrating the latest milestone and reflecting on the last 6 years of solving dating on this podcast. They reflect on how they got here, the best and worst guests, and their most personal episodes. Plus, they play back “Red Flag or Deal Breaker?” segments from years past and guess where they stood. The episode ends with J&J sharing what they want for the pod's future.

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J&J are ready to solve dating again, but first, Jared has a bone to pick with Jorge. Next, a listener is doing just fine in her relationship but wonders what experiences are needed to get her to an engagement. Jordana shares how she and her husband made it past that point, and what hesitations she sensed from the email. The Awkward Encounter is more unhinged than hazardous. Then, another listener is unsure if she should compromise plans with her besties for an important night to her boyfriend. The episode ends with a “Red Flag or Deal Breaker” about bringing up an ex at awkward moments, a SO’s closeness with their ex, and lacking a taste for adventure.

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It’s time for another Sunday Special, but we’re switching it up with a special game. J&J are joined by U Up producer, Jorge Morales Picó, to find out if men think differently when they’re in a committed relationship versus holding single status. Jared and Jorge face off for a series of questions as Jordana puts them to the test.

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It's Halloween, so Jordana came ready to get messy while Jared showed up buzzed–but not in the way you’d think! First, J&J kick off with a pop quiz on spooky season dating terms. Then, a listener asks how he can get his long-distance girlfriend to communicate more. J&J discuss what this could mean for his relationship. The Awkward Encounter involves coworkers too close for comfort and reminds Jared of an awkward encounter of his own. Next, a newly single listener wonders how and when she should address her baggage. Her last relationship ended with infidelity and a divorce, but does every date need to know? The episode ends with a “Red Flag or Deal Breaker?” about food gifts, calling someone “hot,” and using group pics on the apps.

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It’s time for another Sunday Special and, this week, J&J are joined by comedian Sam Morril. He talks unhinged exes and shares a recent text exchange with someone from his past. Then, the trio play a round of “Icky or Picky?” about appetizers on a dinner date. The episode ends with an email asking for validation on a breakup. A listener thought she did her due diligence in breaking up with her ex, but after time had passed and she ran into him, he accused her of not being honest enough because she found a new relationship soon after. Should she have mentioned her crush, or does it not matter if the relationship was on its last leg? Jared, Jordana, and Sam discuss.

@sammorril

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Something major happened and J&J are kicking off this week by announcing the news! After Jordana spills what’s new, a listener writes in asking about how much having a “type” hurts her chances of finding a true match. Then, J&J switch things up from an ordinary episode and make an awkward request. The episode ends with a visit from Jaz Zepatos, a member of the Betches team. She talks to Jared and Jordana about her open relationship, from how it came to be to how she continues to maintain a strong marriage.

@jaz_zapp

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Today’s Sunday Special fits double the podcasts into a bite-sized episode as Jared and Jordana reunite with Girls Gotta Eat podcast hosts, Rayna Greenberg and Ashley Hesseltine. With one host single and the other in a relationship, they discuss their experiences dating in NYC and LA, and the DM slide that led to Ashley’s relationship. Then, J&J ask how not wanting kids has affected dating including when and how this decision is addressed and the stigmas surrounding women that don’t want kids.

@girlsgottaeatpodcast, @rayna.greenberg, @ashhess

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In this week’s episode, J&J settle a few doggy debates among our listeners. Is it worth telling a SO that you hate their dog? Would sharing joint custody with an ex hurt your dating life? Then, the Awkward Sexual Encounter turns out to be pretty wholesome. Jared and Jordana also hear from a listener dealing with ghosting regret, but they think she’s ignoring part of the picture. The episode ends with a round of “Red Flag or Deal Breaker?” about asking your ex for a post-mortem favor, stealing groceries, and social media stalking ahead of a date.

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J&J are back for a Sunday Special and, while the weather is shifting, some things never change. The episode starts with a round of “Petty or Prudent?” about what happens to sex toys after a breakup. Then, we hear from a listener about a classic issue: dating app fatigue. She’s stuck in an up-and-down cycle of being on and off the apps and, while she’s self-aware that this might be affecting her dating success, she feels like this is an individual problem. Jared and Jordana share a reality check, hard truths, and assurances about this listener’s situation.

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A lot has changed since J&J were in the studio a week ago: Jared and Jordana had a first in their friendship, someone wasn’t happy about Jared’s Benefits episode, and Bumble added a new approach to dating on the apps. The first email is about backing out of a talking stage after Jared’s voice gets in her head. The Awkward Sexual Encounter comes in hot. Then, the second emailer questions how she can get her boyfriend to spend quality time with her outside of dates. The episode ends with a round of “Red Flag or Deal Breaker” about a date night don’t, recycling sexts, and lying about your age.

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