U Up‪?‬ U Up?

J&J are questioning narratives today, starting with what happened to romcoms. After seeing Jared’s criticism of “Anyone But You,” Jordana wants to discuss thoughts on Sydney Sweeney, Glen Powell, and the state of romcoms in 2024. Then, we hear from a listener who can’t figure out how to get a guy out of Instagram DMs and into exchanging numbers. Their mutual friends advised her that he’s just “playing it cool,” but it’s starting to feel intentionally avoidant. Next, J&J receive a long email that’s both Awkward Encounter and an ask for advice after a guy friend professed his love at the airport. Our listener is pansexual and feels a tinge of betrayal with her confusion, but J&J don’t think she’s seeing enough of the other side. The episode ends with a “Red Flag or Deal Breaker?” about texting habits, hating travel, and wearing the same shirts.
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Jared is diving deep for his latest Benefits episode! He’s on the road in New Orleans, so the time difference between him and Jordana has him inspired by the extra hour added to his day. Then, he ponders if some of the most likable parts of his personality are part of his problem with dating new people. When you can have fun with just about anyone, how do you know if someone is really for you? He talks to Jordana about the journal he logged on his last French adventure, and how their trip and his current states contrasts from who he was then. Plus, as a true fan of Oversharing, he writes an intention for the week.

The perfect episode to tune in ahead of a Father’s Day brunch, J&J are back with another bite-size Sunday Special. They start with a “Petty or Prudent?” about sending an obituary after someone ghosts you, but they also saw a red flag before our listener got to the point of being ghosted. The episode ends with an email about another TikTok dating trend. Several fun #DatingTok videos are telling single people to try dating with an expiration date, but our listener didn’t have fun with the concept at all. Is it just not for her, or did she do it wrong? The hosts weigh in and advise the workaround for her and anyone else wanting to give this a try.
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J&J are tackling nuance in the modern dating world. Before jumping in, Jordana recounts her Sonoma vacation and her driverless ride reminds Jared of dating apps’ impact on society. Plus Jared has feedback for a fan that shot her shot for an upcoming tour date, and his reasons for what was wrong with her approach tie into the first email. A listener has a crush on her fitness instructor, but is there a way to shoot her shot without making it awkward if he wants to pass? In true U Up? fashion, John Mayer enters the tangent fray, but first, J&J have an introduction to make. Then, the Awkward Encounter involves a situation going from flirty online to uncomfortable irl when a listener finally meets her colleague at graduation. Next, J&J answer an “Are We Dating?” about a long-distance connection growing between traveling work trips. The episode ends with a “Red Flag or Deal Breaker?” about seatbelts, professional Tinder pics, and IG explore pages.
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Jared and Jordana are getting pumped for their trip to Cannes, but they have to get a few things crossed on their list before they go. First up, Jordana needs answers on what the f*ck is up with Jared’s beard? Next, they read a wedding note from a subscriber before delving into a “Petty or Prudent?” about a SIL asking to share a wedding anniversary date. The episode ends with an advice email for a listener’s mom. He’s tried helping her navigate dating after her divorce, but she has excuse after excuse on why no one is right, so he needs help from J&J on how to get through to her.
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J&J are taking on complicated relationships and realizations in this week’s episode, but first, they catch up on Jordana’s latest trip, get excited for their voyage en France, and Jared vents about the unknown era he’s navigating. The first email comes from a listener looking to collect $1,000 her ex owes her. He’s gone radio silent and it’s been a year, but J&J think she’s making a mistake with her ask. Then, our final “Friends to Lovers” submission takes a turn when a listener found her lover’s Grindr messages. TRIGGER WARNING for our next email, we talk about animal abuse. J&J receive an email about an impending breakup, a heartbroken woman, and her dog at the center. She thought he was “the one,” but her dog’s reactions as their relationship progressed caused major issues, and Jared thinks her concern and focus are in the wrong place. The episode ends with a “Red Flag or Deal Breaker?” about dating your ex’s twin, tattoos of faces, and a questionable bachelor party game.
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