We’ve got an update! The Oversharing segment Jared and Jordana disagreed about two weeks ago has extra context, and now Jared feels like apologies are owed (kind of). Then, J&J answer an email from a listener who is considering re-matching with a guy she’s dated before on the apps but she’s worried that he won’t remember her. J&J give her the pep talk she needs to pull the trigger and swipe again. Next, an Awkward Encounter turns a new relationship into a family reunion. The second email is a two-part problem: a listener’s boyfriend is still friends with his exes and she also has a situationship she cannot shake. J&J break down the issues and figure out why we might keep our exes around. The episode ends with a round of “Red Flag or Deal Breaker” about a first date foul, Eras tour tickets lie, and a tacky gift.

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It's one of our last Sunday Specials before we move to Fridays (read: Thursdays, if you're a subscriber)! J&J kick off with a round of Couple's Court about deleted nudes. Our listener got a weird feeling (iykyk) about her bf, so her gut told her to look through his phone. It looked clean at first until she found deleted nudes of him--and another woman, but here's where it gets strange: he told her that it was just a porn subscription, and the porn star requires him to exchange nudes on Snapchat. When you're done rolling your eyes, listen and get ready to weigh in on whether this is truly an open and shut case. Then, J&J help another listener navigate whether she should consider getting back together with her ex or walk away. He clearly had commitment issues when they were together, but now that they're apart, he took her advice to go to therapy. J&J discuss the boundaries she needs to set moving forward and if his decision to go to therapy is enough to open the door again.

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Spooky Season has officially started and Jordana kicks us off with an update about the odd happenings in her apartment building. Then, Jared recounts his own bizarre experience that happened the night before. Plus, they weigh in on WalletHub's "Best and Worst Cities To Date In 2024". The Awkward Encounter turns a listener's kink into an ick. Next, a listener who wants to know why men always seem to always settle down after they end a situationship where they couldn’t commit. The episode ends with a round of “Red Flag or Deal Breaker” in partnership with Netflix, including a shared bathroom debate, a long-distance situationship with friends who are possibly too persuasive, and a vegan surprise.

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J&J are easing into another Sunday Special with a quick check-in on the current states of their minds. Jared shares how his new hobby, golf, is one way to watch a man’s insecurities unveiled. Plus, Jordana is going stircrazy in her temporary home while she’s waiting for her house to finish major renovations. Next, they play a round of “Icky or Picky?” about a first date to a nude beach. Afterward, a 29M listener writes in concerned about the trajectory of his relationship. He and his fiancée are feeling less compatible as their relationship goes on, but is he stuck because he already proposed to her? Jared and Jordana take issue with the focus of his email and discuss the importance of communication and knowing when to call it quits.

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We’re navigating second-guessing today! Jared tells Jordana about his latest trip to Boca, when his parents started dissecting why he’s still single, and Jordana pulls him out his own head. Afterward, they get an email from a listener concerned that her boyfriend is too much of a green flag. She spent her 20s dating toxic “boys,” so why isn’t she satisfied in a stable relationship with a mature man? The Awkward Encounter is a funny story that’ll have you clearing your Google search history. Then, a woman writes in after getting disgusted by her aunt’s reaction to meeting her boyfriend. The episode ends with a “Red Flag or Deal Breaker?” in partnership with Angry Orchard, about sharing locations, a killer dating app DM, and TikTok thirst traps.

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We’re coming full circle as actress and filmmaker, Heather Graham joins J&J for an extra special Sunday episode. 2 years ago in a Benefits episode, Jordana shared the story of how Heather Graham’s list for manifesting the perfect partner led her and several friends to meet their husbands in a matter of months, and Jared made a list of his own too. Fast-forward to present day where a listener wrote in to announce she’s getting married and those episodes helped her find her man too, so it was finally time Heather Graham knew her impact on the U Up? World. After J&J bring her up to speed on her unknown history with the pod, she shares her affirmations, how her friend group wills what they want into their lives and the ways she’s learned to make better choices than what may feel familiar to someone with a dysfunctional past. The episode ends with a lightning round of “Firsts & Worsts.”

For more from Heather Graham (@heathergraham), see her sophomore directorial project, “Chosen Family” on October 11, 2024.

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J&J are back in the studio and with the way the U Up? world works, it’s still Jordana’s birthday. They get excited about everything fall has to offer, from dating and the NFL to fall fashion. Plus, a subscriber helps Jordana amend a remark from last week’s chat about Chappell Roan, and Jared gets a touching message from a fan. The first email comes from a 31F listener who’s starting to feel like she’s mothering her 26M partner. Is this a slight play at weaponized incompetence, or just a serious lack of awareness? The Awkward Encounter is a building ick as a 35F listener is struggling to deal with her BF’s snoring or morning kisses while he’s wearing a mouthguard. Next, a listener feels like she won’t get out of her own way when it comes to great matches she’s met on dating apps. The episode ends with a round of “Red Flag or Deal Breaker?” about backrubs, a surprise home visit, and unsolicited business advice, in partnership with Angry Orchard.

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J&J are reminding us of the “disgustings” they are in today’s Sunday Special, but you’ll forget all about that by the time you hear how unhinged the advice email is. After catching up, they play a round of “Petty or Prudent?” that throws us back to the topic that inspired this segment: sharing streaming services. Is it petty or prudent to kick an ex off of your streaming accounts after a breakup? The episode ends with an advice email from a 40M listener hung up on sex in past relationships despite hearing “wedding bells” for his current partner. Looking beyond the red flags being waved, J&J sense something more problematic going on.

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Jordana is back from her trip to "Fra" and we’re getting a full recap, which includes her very own Britney Spears moment. Then, in a strange turn of events, we get a dramatic reading of a Chappell Roan song from Jared. Next, we hear from a listener who has an unwanted third person in her relationship: her boyfriend’s brother. J&J try to read between the lines and figure out what this actually means for her relationship. Then, an Awkward Encounter from a listener whose mom opened a very private package. Finally, a love story from a listener who met her dream guy at the Renaissance faire. Is it too far-fetched to travel to another state to pursue her (maybe) knight in shining armor? The episode ends with a round of “Red Flag or Deal Breaker,” in partnership with Angry Orchard, including a partner with a very sexy hobby, a kiss with a childhood crush, and a first date who chose an interesting seat.

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On this Sunday Special, Jared and Jordana hear from a listener who has been engaged not once, not twice, but three times without ever making it to the altar. Is anyone ever 100% certain before walking down the aisle? First, Jared shares a recent plane mishap that has him thinking that he'll make a good boyfriend one day. Next, they receive a "Couple's Court" from a listener who has beef with her boyfriend's beard, reminding Jordana of a constant grooming conversation she has with her husband. J&J recreate the conversation they think this listener should have to get exactly what she wants.

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