Bethenny Frankel’s TikTok about pen pals sparks a debate between J&J and questions why this trend is still a topic years later as if it’s brand new. They act out how to handle a pen pal in dating when texts keep coming but no plans are being made. Later Jared and Jordana read a petty or prudent email about an ex still making NFL survivor pool picks after a breakup. They then question what counts as creepy and whether an age gap is a valid concern. J&J discuss age gaps in dating and explain when it is fine for older men to ask younger women out.

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This episode starts with Jordana sharing how her cute puppy Ronnie gave her an unexpected wake-up call, which even led to her losing her phone! J&J then dive into listener advice, reading about a woman dating outside her faith and offering tips on handling her traditional parents while explaining why meeting the person matters more than expectations. They break down twins posting matching photos on dating apps, define what a “mini makeout” really is, and roast the worst breakup text clichés like “I’m rooting for you” and “you deserve better.” Plus, they debate whether snoring or using a CPAP machine is a deal breaker or just a lame excuse?

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On this Friday’s Feels ep, J&J review You’ve Got Mail, the iconic Upper West Side rom-com starring Tom Hanks and Meg Ryan, diving into the movie that kicked off the era of online dating while nostalgically saying goodbye to small bookstores. They explore the magic of falling in love online before apps made dating complicated, from over-30 chat rooms to the classic AOL dial-up sound that defined a generation. From slow, meaningful email connections to Joe Fox’s low-pressure dating style, they debate whether this vintage romance still holds lessons for modern love. Plus, they question if Kathleen was actually forced to fall for Joe after his store puts hers out of business, wondering if romance can survive a little ruthless competition.

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J&J go virtual and Jordana recaps her time at a wedding and dives into the buzz around ZYN nicotine pouches, the Gen Z trend creeping into adult life. They dish on dating dilemmas like when a guy stalls intimacy and the tricky etiquette of phone number exchanges. Plus, they weigh in on dancing at weddings, and how not dancing can be seen as a turn off. During the red flag dealbreaker segment they learn about a guy who refuses to ever give gifts to couples, to which Jordana jokes, “If I ever married this guy, we would get no gifts!” They also tackle an icky or picky moment where a listener likes the guy, but can’t get past all that back hair!

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Jared and Jordana realize it’s October 3rd! The “basic bitch Christmas”is a perfect fall day as it is Taylor Swift’s album release, Mean Girls Day, and a perfect day to drink spice lattes and put on a Gilmore Girls marathon. Jared takes on “Rejection October,” trying to get turned down three times, while they also break down a first date gone icky when the guy pressured a tired listener to reschedule. Plus, they analyze a performative ex sending unsolicited travel updates, showing how some people use breakups to make themselves look good.

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Jared starts off the podcast with a redflag dealbreaker he heard: a straight guy has been to 30 Taylor Swift concerts. He and Jordana debate whether it makes him a groupie, a walking turn-off, or just a man who unapologetically loves what he loves. They help a woman who writes in who is dating without wanting kids, and why singles constantly get dismissed with “maybe you’ll change your mind.” A listener wonders if it’s icky or picky that her chef boyfriend eats PB&J every single day, and another listener confesses a crush that ends with the dreaded “don’t wait for me.” Plus, J&J prove that the best dates can cost just $10, and break down what it really means when your partner hides a secret Finsta!

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Jared is feeling “very single” these days, a term he never thought he’d describe himself as! Jordana and Jared dive into the latest dating trends, from “Shrekking” and dating down with charm to the etiquette of bringing a plus one to a wedding. They also tackle hilarious friendship dilemmas like telling someone their dog smells, they have B.O., or if a guy has gone overboard with Botox. Would you be brave enough to tell a friend if they smelled?

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Dating fails, ghosting, and awkward first dates collide in this week’s episode of U Up? with Jared and Jordana. A listener writes in wondering if he was unmatched on Hinge by mistake or if it was just ghosting in disguise? J&J give another listener step-by-step advice on how to ask out a roommate without creating a “half-boyfriend” or awkward living situation. Plus, they dive into a few red flag dealbreakers: Venmo requests before dinner, and first date Groupons. Red Flag? Or just not sexy? Jared also pitches a clever idea for single-person restaurant menus so you can try more food without wasting a full plate!

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Jared and Jordana are joined this week by Dateable podcast hosts Julie Krafchick and Yue Xu on U Up? Julie opens up about her journey as a self-proclaimed “type A dater” and how letting go of control ultimately led her to the right partner. She was just married last Saturday, with Yue officiating the wedding. Yue shares the shocking story of discovering her long-term boyfriend was cheating while she was writing a dating book, and how interviewing “the other woman” on their podcast became one of the most therapeutic experiences of her life. They also play “Icky or Picky: Fashion Edition,” debating whether showing up underdressed to a fancy restaurant is an ick or just being picky.

Check out more on Dateable here 👉 Take the ⁠Dating Archetype Quiz⁠, check out ⁠How to Be Dateable⁠, and listen to ⁠“The Other Woman”⁠ episode too!

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Jared and Jordana dive into the small etiquette moments that can make or break a date, debating whether table manners like placing a napkin on your lap or holding a fork the wrong way are serious red flags. They explore celebrity engagements from Taylor Swift and Travis Kelce to Brooklyn Beckham and the real-life pressure couples feel on their own timelines. Listeners write in with wild dating stories, from a guy who lies about it being your birthday to a baseball hat worn on back-to-back first dates, and Jared and Jordana unpack whether these are quirky personal choices or dealbreakers. They even tackle unconventional living situations, like sharing a home with grandparents, weighing when this is endearing or potentially a red flag.

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