U Up?

This week, J & J are fresh off a dinner party together, but Jared’s own awkward encounter at a bar afterwards has him regretting that nightcap martini. After some daydreaming about winter getaways, we dig into the e-mails, starting with a listener who put their friend onto the pod, watched them succeed at finding love, but keeps striking out on their own. They tackle a couple of listener’s dating app woes, like should you stop replying if they make an edit to their profile you really dislike? Today’s "Awkward Encounter" pushes the boundaries between “awkward” and “heartbreaking,” with a write-in from a woman who thought she was getting a ring but got a break-up instead. Keeping the New Year unhinged, “Red Flag or Deal Breaker” covers disclosing food allergies, being pushy about “going to my place”, and talking about your parents sex lives on a first date… which we think might require a little more professional help. Learn more about your ad choices. Visit megaphone.fm/adchoices

Dating Coach, Hinge Relationship Science expert, and friend of the pod Logan Ury (@loganury) is here to help J & J answer the question haunting single women everywhere: Where are all the guys?!? Her new Netflix show “The Later Daters,” where she coaches singles over 55 on how to get back in the dating scene, is now streaming – and proving that some dating struggles never change, even with age. They really dig into Logan’s 2025 passion projects: the gender imbalance in dating, the need for male support networks, and how we can improve the male end of the dating pool. We hear from one listener who wants to know if being single for years makes them undateable, but Logan’s here to assure us all that it’s never too late to find love. All of this tees up Monday’s special Benefits episode: Logan coaching Jared, on air, no holding back. You won’t want to miss it. Learn more about your ad choices. Visit megaphone.fm/adchoices

Happy New Year, U Up? listeners! J&J are ringing in the New Year doing what they do best: going a little bit off the rails. Jared plans to celebrate the New Year by toasting his martini to the moon (and hopes you will toast him back, wherever she is). They reflect about their 2024, before diving into some of Jared’s 2025 dating resolutions which include new-and-improved dating lines, personal improvement, and why you should be an even worse first date. Then, we hear from one listener who wants to know if she should be vision boarding her relationship, and an older listener grappling with a middle-aged breakup. Finally, we end with a quick “Red Flag or Deal Breaker,” where every write-in has us asking, “what’s going on with men??” Learn more about your ad choices. Visit megaphone.fm/adchoices

The holidays are coming to a close, the New Year is looming – is it time to get your shit together? We’re ending 2024 by welcoming author, entrepreneur, and returning guest Ramit Sethi (@ramit) to the studio for a (seriously) fun conversation about money and relationships. His new book, "Money for Couples", is about how to create your most "Rich Life." It’s a touchy subject, but Ramit holds our hand through it all: how to broach the money convo early on, reframing financial conversations through a more romantic lens, what you might not be considering when thinking about engagement rings, and so much more. Plus, we hear from a male listener struggling with gender-based expectations when it comes to paying on dates – why is it so awkward to go Dutch? We wrap things up with a rapid fire game, “Fund It or Forget It.” See you in 2025! Buy Ramit Sethi's book here. Check out Ramit Sethi's 2022 U Up episode on Apple or Spotify. Learn more about your ad choices. Visit megaphone.fm/adchoices

‘Twas the U Up? before Christmas so J&J dressed up for fun. Regardless of your holiday plans, you won’t want to miss this one! With unhinged holiday spirit taking over the entire studio, they play a round of “Naughty or Nice?”, offer up Jared’s first date of 2025, and end with a holiday competition of ‘Twas The Night Before Christmas rewrites by Jared and our producer, Candice. Plus, the Awkward Encounter involves a feline funk and J&J give a reality check when a cheating woman writes in with hopes for her next relationship before she’s ended her current one. Head to our Instagram @u.up.podcast to vote on our pod poetry and get details on how to win a date with Jared. Learn more about your ad choices. Visit megaphone.fm/adchoices

What does 2025 hold for your love life? Kelley Knight (@kelley__knight), psychic and owner of Modern Mystic Shop, returns to the studio to help us see what’s in store for each of our futures! First, she surprises J&J with gifts and they catch up since she gave Jared a reading in an episode last December. Then, Jared and Jordana each ask a question about different aspects of their lives for a quick reading. The episode ends with a round of Tarotscopes as Kelley makes predictions for each zodiac sign, with our hosts and producers paying extra attention to our own signs.For more from our guest, follow @modernmystic_shop or visit modernmystic.com  Learn more about your ad choices. Visit megaphone.fm/adchoices

After a couple weeks away from the studio and just days after Jared’s special taping, Jordana starts this episode by giving Jared his flowers and catches him up on her girls’ trip as the hosts settle back in. The first email asks for advice for everyone traveling to stay with family over the holiday season. How do you balance dating and family time when you’re away from your city, but don’t want to take a break? The Awkward Encounter, sponsored by A24’s Babygirl, comes from a woman unsure when to bring up her kinks to find the right partner. Next, a listener with a calculated approach to her dating life is starting to second-guess herself after her friends’ judgment about her current situation. The episode ends with a round of “Red Flag or Deal Breaker?” about family baggage, an angry cat, and a vegan’s roach reservations. Learn more about your ad choices. Visit megaphone.fm/adchoices

Feeling lucky? On par with Friday the 13th, Jared and Jordana ease into the episode with their thoughts on superstitions, energy, and beliefs. Plus, Jared shares where his head is at ahead of a recording break for the Thanksgiving holiday, Jordana’s trip, and his special taping. Then, they play a game called “Is That My Wife?” inspired by Jared’s DMs. The episode ends with an email from a 26M listener wondering if he should be feeling more for the woman he’s been seeing for a couple of months or if dating in the digital age has skewed his perspective. Learn more about your ad choices. Visit megaphone.fm/adchoices

Why won’t Jared go to therapy? We get this question often and, this week, he shares his own thought on why as well as a helpful TikTok, "Men Who Wear Masks And Struggle With Conflict" by @elisemicheals. Plus, he and Jordana are slipping more into f*ck it mode for the holidays. The first email is advice ahead of office holiday party season when your coworkers knew your ex: how do you introduce your new boyfriend to your coworkers without any awkward moments? The Awkward Encounter has a strange condom request. Then, we hear from a listener who’s growing frustrated with a conversation ick with the guy she’s dating. Every time she shares a story, he somehow makes it about himself. Can they get over these conflicting communication styles? The episode ends with a “Red Flag or Deal Breaker?” about turning a submission into a Hinge prompt, an off-putting first date experience, and acting like a baby when you’re sick Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are feeling good for this Friday episode with big plans for both hosts, and with this kind of energy, you never know where the conversation will take them! As you’ve seen on IG Stories by now, Jordana should be on her way back from a group trip and Jared is gearing up for his special taping in Tarrytown. With live performances on their minds, and as with most conversations lately, Wicked finds its way into their chat–except it just has Jared missing when he was into Marvel movies. Plus, Jared gets a lesson in chlamydia (yes, chlamydia) from Jordana ahead of his Australia trip. The episode ends with a reveal: with soulmate drawings picking up on TikTok, Candice commissioned a reading for Jared. J&J react to the predictions from the Etsy psychic. Learn more about your ad choices. Visit megaphone.fm/adchoices

We’re officially in “let’s circle back in the new year” territory, and to embrace it, J&J set out to make this the most unhinged U Up? episode this year. They talk about the pursuit of meaningful relationships and how the distraction of dating apps is clouding the way for the people making actual efforts. Plus, after the public reaction to Benny Blanco sharing that his relationship with Selena Gomez started by her asking him out*, they talk about the public’s perceptions of their relationship and the obstacles that even Selena has faced as a successful woman that wants to find love. The first email comes from a listener writing in from the post-date Uber: what are the signs a guy wants you to leave after sex? She shares what she took as signs to leave, and J&J weigh in on whether she overthought the situation. The Awkward Encounter comes from Genova as a listener has an unusually sexual sight in her new city. The next email is questioning whether to act on being called “The One That Got Away.” Our listener’s

It’s the biggest shopping day of the year, but before you get the new iPhone 16, J&J want you to know how a new AI feature on the iOS 18 update could affect your dating life. With breakup texts submitted to our Instagram and a ChatGPT assist from our producer, Shannon, Jared and Jordana break down how the conversations went and generate what an AI version would look like. They also determine when a breakup text is appropriate and play out their own breakup scenarios. The episode ends with a round of “Icky or Picky?” about proposing a shopping spree for a first date. Is this a fun way to get spoiled for a few hours by a dating app rando, or is it just creepy? Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s officially our favorite time of the year and J&J get a little unhinged today as they amp up for what’s to come! They come in hot with a fresh new rant about TikTok’s favorite couple, Pookie and Jett. Plus, because the holidays are a tricky time for love lives regardless of status, J&J are guiding you through Thanksgiving and the start of holiday season with a lightning round of advice. They listen to a slightly shady voicemail from a curious mom and answer a range of Instagram submissions covering various holiday hiccups, from early dating momentum to interfaith relationships and in-law issues. Learn more about your ad choices. Visit megaphone.fm/adchoices

We're at the end of cuffing week to prep you for the cuffing season ahead, and Jared and Jordana are doing temp checks on the unofficial statuses between casual, comfortable and committed. First, Jordana gives us a home renovation update and Jared shares a sad breakup story of his own. They play a round of "Icky or Picky?" about getting too comfortable wearing weird PJs too soon. Plus, a 27F listener needs advice on whether or not to build a roster to kick her dating life into high gear. The episode ends with a new game, "Cuffed or Casual?" as J&J weigh in on Instagram submissions of confusing moves that could be deemed as nothing serious or a sign that the other person wants a real relationship. Learn more about your ad choices. Visit megaphone.fm/adchoices

The holidays are getting closer and the weather is getting colder which can only mean one thing: cuffing season is here. Jared and Jordana delve into the discourse around cuffing season and discuss controlling the narrative around your dating life. Then, a 27F listener writes in to ask whether wanting casual sex is derailing her dating goals. She's never had a real boyfriend; is abstinence the only way she'll ever find one? The Awkward Encounter involves a situationship with a love kink. Next, a listener with a tumor diagnosis asks how to address her medical journey while dating. The episode ends with a round of "Red Flag or Deal Breaker?" about sharing your life with your SO, updating Hinge daily, and owning only one cutlery set.  Learn more about your ad choices. Visit megaphone.fm/adchoices

It's our anniversary! 7 years after the first U Up? episode, Jared and Jordana walk into a decorated studio themed to the traditional 7th-anniversary gifts: copper and wool. First, J&J exchange gifts, then they talk about what the dreaded 7-year itch means in relationships. Next, Jared and Jordana reveal their lists of what they want for the pod's future. The episode ends with a lightning round of U Up? history and reflecting on top pod moments since our last anniversary. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared fills Jordana in on his bizarre and funny late night Halloween experience and they also discuss the new Martha Stewart documentary. They hear from a listener who is struggling with communication from their partner. Next, they hear an Awkward Encounter that ends with them walking in on somebody in bed with another girl. Then, they discuss an email from a listener who isn't sure how to know if a relationship is serious if they both don't want marriage. Finally, they dive into a round of "Red Flag or Deal Breaker?" featuring a fat-phobic date, a boyfriend unwilling to compromise, and Olivia Rodrigo's number one red flag. Learn more about your ad choices. Visit megaphone.fm/adchoices

DISCLAIMER: This episode was recorded prior to the election. Jared and Jordana divulge the complexities of dating during an election year and how to navigate discussing politics on a date. In this week’s "Icky or Picky?" a listener wants to know if their date littering dog poop is something worth overlooking. Next, they tackle a listener’s dilemma concerning her date's disappointing "whiskey dick" and Jared opens up about male performance anxiety. Learn more about your ad choices. Visit megaphone.fm/adchoices

We're officially headed towards the toughest times to date—cuffing season and the holidays—so Jared and Jordana discuss how to navigate this tricky period. They hear from a patient whose attractive doctor makes her temperature rise but she's unsure whether to make a move or not. Next, they hear an Awkward Encounter about life at boarding school. Then, they discuss an email from a listener whose boyfriend is extremely jealous and suspicious of her male friend. Finally, they dive into a round of "Red Flag or Deal Breaker?" about toilet plungers and gift giving etiquette. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana break down artist Spritely’s viral TikTok breakup video, unpacking relationship red flags, communication pitfalls, and the complexities of moving for love. In this week’s "Icky or Picky?" a listener asks if designer labels make or break a date J&J agree, no one should feel judged for their fashion choices, no matter the brand. Next, they tackle a listener’s dilemma about tracking down a Bumble match from nearly a year ago. Is her search romantic or just plain extra? Jared and Jordana empathize but offer a crucial reminder: while bold moves can impress, more than one follow-up message might push things into red flag territory. Learn more about your ad choices. Visit megaphone.fm/adchoices