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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Jared and Jordana are back with another Sunday Special, and this week they’re tackling the age-old “right person, wrong time” question. The emailer sends in screenshots of the very nice breakup text she received after two great dates. He didn’t want to keep dating because he was moving but told her to let him know if she was ever in his new city. Fast forward a year, and she’s moving there for work, so should she ask him to grab a beer? J&J break down all the possibilities she should think about before she reaches out.

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This week’s episode starts with a big shame on Jordana for straying from Delta Airlines for her trip to Hawaii and the Bach By NoonTM plan for Park City. Then they dive right into the second half of your Lightning Round questions about everything from moving in with your long distance S.O. to making a coffee date actually feel like a date. Plus, Jared gives the world’s saddest pep talk. Detours include planning where Jared would move for a date and Jewish mom erotica.

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J&J are back with our first Sunday Special of October, and they start with a chat about Jared’s trick or treating observations from last year and Jordana’s days as a babysitter in the city. Then, they dive into the email from a listener whose husband wants her to lose weight. They’ve both been on their own health journeys, but she’s healed her relationship with her body and he’s still struggling. After he revealed he prefers a thinner body type than hers, she asks if she should try to lose the weight for him. Would that solve any of their issues in the long run? Plus, they talk about the best way to address it without putting him on the defense.

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