U Up?

We love a Sunday Special, and this week J&J are answering an email from a listener who’s struggling to bond and set boundaries with her boyfriend’s family. After an awkward dinner with his family where they left her with more than half of the bill, she’s wondering when she can have a conversation with her boyfriend about her inability to relate to them. How much can she expect her boyfriend to defend her? Plus, Jared talks about how he handled similar issues in his own relationships.

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On this week’s episode, Jordana and Jared start with a recap of their Halloween weekends and a warning to single people with the new iPhone. The first emailer asks how to handle a breakup with her boyfriend of 5 years when neither of them can afford to move out. J&J dish out the hard truths of the situation and her responsibilities as the dumper. The Awkward Sexual Encounter is a study abroad adventure. Later, a listener asks why his friends won’t set him up. As the resident set up expert, Jordana gives some potential reasons they’re not telling him, and Jared breaks down how his attitude toward dating might be playing a role. J&J are joined by Fortune Feimster to finish the episode with a round of Red Flag or Deal Breaker about exes on Instagram, Hinge profiles, and the wrong times to bring up your mom.

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J&J are back with another Sunday Special, and this week they start with a conversation about Jared’s run-ins with Al Roker and the “seven year itch.” The emailer asks if you have to reply to a breakup text after she gets one from a guy she was dating exclusively for four months. Jared and Jordana break down each line of the breakup text, and Jared shares some relevant experiences from his dating life. Plus, they tell the audience exactly what *not* to say in a breakup text.

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Jared and Jordana are back with the first episode of November. They start with a discussion about Jared and Jordana’s favorite holidays and break down what it means when people say they’re “so single.” The first emailer asks if a guy not asking any questions about her is a reason to end the relationship. J&J rephrase her email to help her see this situation clearly. The Awkward Sexual Encounter involves some improper condom disposal. Later, a listener asks why old situationships pop back up once you get into a relationship. What are they hoping to get out of this? They finish the episode with a round of Red Flag or Deal Breaker about mice, cash gifts, and cheating friends.

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J&J are are joined by special guest Delaney Rowe for a spooky Halloween Special. They start with some horror stories about UTIs, DM slides, and the meanest comments they’ve gotten online. Then they dive into Delaney’s dating life and how her career has impacted it. In the spirit of spooky season, they answer an email asking whether or not it’s ghosting if both people stop texting. Is “ghosting” overused in general now? Plus, Delaney asks Jared why men make promises they don’t intend to keep.

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On this week’s episode, J&J start by launching Jared’s presidential campaign to fix Halloween scheduling and giving some Halloween dating tips. The first emailer asks if “He’s Just Not That Into You” holds up in 2022. If the guy she hung out with once wanted to see her again, wouldn’t he just make a plan? What do people actually mean when they say “if he wanted to he would”? The Awkward Sexual Encounter is a cautionary tale for sports bar hookups. Later, a listener asks how to recover from the first fight with her boyfriend. They made up, but she’s still feeling self-conscious in the relationship. Is this just the end of the honeymoon phase? J&J finish the episode with a round of Red Flag or Deal Breaker about “crepe-fishing,” flossing, and concert etiquette.

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J&J are back with another Sunday Special, and this week they’re joined by Ramit Sethi, author of “I Will Teach You To Be Rich.” They start with a conversation about Ramit’s work with couples to change their mindsets on money, and he gives an exercise for couples to open up the conversation about their finances. Later, they answer an email from a listener wrestling with an income difference in her relationship. She’s moving in with her boyfriend who makes $300k more than her, and she can already feel the resentment building. How should she handle his snarky comments? Plus, they talk about how important non-monetary contributions are to relationships.

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On this week’s episode, Jared and Jordana start with a recap of Jordana’s weekend with her entire family and Jared’s bloody mary tour of Milwaukee. The first emailer asks if she’s gotten too comfortable being single after a friend told her she feels like she’s giving up. Does she need to put herself out there more or should she continue focusing on herself? The Awkward Sexual Encounter involves a “king size” man and a CPAP machine. Later, J&J listen to a voicemail asking how to approach dating apps when you definitely don’t want kids. Should she avoid guys whose profiles say they do want kids? Is she too worried about wasting her time? They finish the episode with a round of Red Flag or Deal Breaker about nosey friends, football obsessed boyfriends, and couples costumes. 

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J&J are back with another Sunday Special, and this week they're talking about being friends with exes. Jared and Jordana share their own experiences trying to be friends with exes and how that idea changes as you get older. Then, they dive into the email detailing a listener’s relationship with her ex from college. They broke up but stayed in touch through their friend group, and they eventually ended up in the same city again. When she told him she was thinking about getting back together, he said he wanted to stay friends, but now that she’s dating someone else, he tried to make a move. Why is she so committed to being friends with this guy anyway? Plus, J&J discuss the hard truth behind every breakup and the problem with romanticizing your exes.

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Jared and Jordana are back in the studio for this week’s episode, and they start with a recap of Jordana’s trip to Hawaii and a look into her family dynamic with 9 siblings. Jared updates Jordana on his dating goals from his latest U Up? With Benefits episode. The first emailer asks if guys care less once the relationship becomes official after noticing her new boyfriend has been putting in a lot less effort. Should she “match his energy” or speak up about her annoyance? The Awkward Sexual Encounter is a Lizzie McGuire style escapade. Later, J&J read an email from a listener who can’t stop obsessing over exes who seemed to disappear after the breakup. She’s in a happy relationship, so why can’t she stop trying to keep tabs on them? They finish the episode with a round of Red Flag or Deal Breaker about missing teeth, bluelight glasses, and dating app openers.

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