U Up?

We love a Sunday Special, and this week, Jared is in his Samantha Jones era. This week’s email comes from a guy getting mixed signals from a barista. She keeps saying they should hang out, but when he tries to make plans, she flakes. Why even bring it up in the first place? Plus, J&J talk about the problem with being a people pleaser in dating.

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J&J are back in the studio for this week’s new episode, and they’re starting with a conversation about Jared’s recent spa experience and Jordana’s upcoming girls trip. The first emailer asks how she can revive some of her old dating app matches since her chat archives are full of guys with potential. Is it desperate to message someone on the apps months after the conversation ended? The Awkward Sexual Encounter is a series of unfortunate events in Jared’s least favorite place. Later, an emailer asks how to get her husband to improve his hygiene. They finish the episode with a round of Red Flag or Deal Breaker about familiar faces, coupons, and “breast friends.”

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On this week’s Sunday Special, Jared gives his weekly dispatch from Boca. Then, J&J read an email from a Pilates instructor who went on a few great dates with a client before getting a text saying he wasn’t in the right mindset to date. She accepted the break up, so why did he reach out again a few weeks later? How much does his relationship history factor into this behavior? Plus, Jordana explains the most annoying parts of what he’s doing.

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On this week’s episode, Jared and Jordana start with a recap of Jared’s big week on the dating apps before NYE, including a date he went on in Boca. The first emailer asks if she should let her guy best friend out of the friend zone. They’ve been going on dates and expressed romantic interest, but she just can’t imagine having sex with him. The Awkward Sexual Encounter involves a surprising discovery. Later, a male listener who keeps getting the “you’re so great, but I’m not feeling a romantic connection” text after first dates writes in to ask what he’s doing wrong. Is his problem that he’s actually being *too* romantic? J&J finish the episode with a round of Red Flag or Deal Breaker about shower frequency, middle names, and date plans (or lack thereof).

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On this week’s Sunday Special, Jared and Jordana start with a discussion about Jared’s struggle to get to the fifth date. The emailer asks how to set boundaries with a friend she tried to date but ultimately decided wasn’t the match. She was really upset by their breakup, but she’s trying to play it cool which ended in them drunkenly making out (shocker). How can she set a boundary with this guy without making it weird for their friend group? Plus, J&J explain the problem with being the “cool girl.”

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On this week’s episode, J&J start with a detailed discussion about ice luges and Jordana’s most recent fan interactions. The first emailer writes in asking if “cute if you’re into it, creepy if you aren’t” is valid in all situations after she saw this explanation all over the comments section of a woman’s TikTok about a bad date. Is it really men thinking about it this way or just men on the internet? The Awkward Sexual Encounter involves a very oblivious emailer. Later, an emailer asks how to handle taking out her Invisalign liners on first date. J&J finish the episode with a round of Red Flag or Deal Breaker about the Batmobile, subtle insults, and bad cooking.

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J&J are back with the first episode of 2023, so they start by reflecting on 2022 and making resolutions for 2023. Then, they dive into the Deal Reveal about a miscommunication early in a relationship. The emailer explains that the guy she’s been seeing stopped communicating with her after she made a joke about having another date. When she calls him out on it, he comes back with a lot of excuses, including misunderstanding her joke. How much do his excuses matter? Was her joke really the problem here? Plus, Jared and Jordana critique her original call out text.

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Jared and Jordana start this week’s episode with a recap of Jordana’s trip to Australia and a conversation about the magic of December in NYC. Then, they talk about why it’s so hard to keep dating momentum going during the holidays. The first email asks how to get to a first date when you’re not on the apps. The Awkward Sexual Encounter involves a broken table and an attempted robbery. J&J finish the episode with a round of Red Flag or Deal Breaker about happy places, cousins, and ferrets.

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J&J are back with another Sunday Special, and this week, they start with a full rundown of Jared’s sushi order (just what you wanted for Christmas, we know). This week’s emailer asks how soon is too soon to talk about mental health in dating after a guy asked to reschedule their second date due to an episode of depression. Is she wrong to be turned off? Plus, Jared and Jordana talk about what real emotional availability and vulnerability looks like.

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On this week’s episode, Jared and Jordana start with a conversation about Santacon in NYC and a follow up from the Awkward Sexual Encounter from our 12/7 episode. The first emailer asks if men are getting cheaper after more of her recent first dates accepted her offer to split it. Are these guys into equality or just not that into her? This week’s Awkward Sexual Encounter involves sisters with a lot in common. Later, a listener asks J&J’s opinion on a Curb Your Enthusiasm theory about non-single people “safely” flirting with other non-single people when their significant others aren’t around. Is this type of interaction as harmless as it seems? They finish the episode with a round of holiday-themed Red Flag or Deal Breaker about dog holiday cards, ugly Christmas sweaters, and NYE kisses.

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