U Up?

Jared’s Netflix special is coming out in the fall and he recalls a roasting bit with Rob Lowe, and why meeting him completely changed his mind. J&J then debate whether it's petty or prudent for a guy to text his ex that he won a $50 competition just one week after dumping her. They also unpack a breakup over indefinite travel, questioning if it’s a right guys, wrong time moment? They discuss why women convince themselves they'll never find another great connection, and Jared's rule that you should never say "you" in a breakup!
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Jared and Jordana debate whether dating a diehard Philly’s sports fan is a harmless quirk or a real relationship problem. Can passion be just plain obnoxious? They also unpack the internet debate over women proposing to men, why Taylor Swift rumors about an MSG wedding sparked such strong reactions, and reminisce about the glory days of Fire Island share houses after college. J&J also discuss first date bill split etiquette: it's not really about the money, it's about the communication.

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Jared and Jordana are getting ready for Fourth of July weekend, where Jared will be staying with Jordana, finally! Then Jared shares the funniest wedding guest he's ever met, a guy with Oakleys on the back of his head who somehow became the life of someone else's wedding. Plus, they debate whether sending a hotter guy to pick up your stuff after a breakup is petty or genius, and help a listener whose future in-laws keep letting themselves into the house, cleaning, dog-sitting, and crossing every boundary imaginable. It's an episode about weddings, breakups, overbearing families, and why sometimes "helpful" can go way too far.
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Jared is back from his book tour convinced dating is rougher than ever, and he and Jordana break down why so many singles are feeling burnt out. Then they tackle whether asking for someone's Instagram or Snapchat before a first date is a hookup red flag, if you should reply when an ex apologizes 12 years later, and whether all men over 40 on dating apps deserve the bad reputation. Plus, is it fair to ask your boyfriend to wear pants around the house, and does living together "feeling like a vacation" actually mean you're not being taken seriously? It's a packed episode full of dating hot takes, relationship debates, and the kind of questions every couple will end up arguing about.
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Jared shares the wildest piece of weight loss advice he's ever gotten from a fan at a country club, leading to a discussion about criticism, internet comments, and why the people who care enough to complain might actually be your biggest fans. Then, J&J debate whether it's an ick or just being picky when a hinge date pulls out a Bible app and reads a favorite verse at a dive bar over chicken salad sandwiches. Too passionate? Later, a listener discovers her boyfriend secretly asked ChatGPT if he should break up with her and finds a list of complaints about her! Is using AI as a relationship therapist a red flag, or is reading someone's private doubts the real problem? J&J have some thoughts! Our last email was originally inspired by Lindsey Hall's Substack, I Stumbled Across My Boyfriend's ChatGPT and It Ended Our Relationship
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