How Long Into Dating Someone Should You Expect To Have Valentine's Day Plans?

Fall is for flirting, but dating comes with its own set of challenges, especially when reality TV obsessions, sports fandom, or constant phone use get in the way. Jared and Jordana break down what makes a relationship work, from the perfect season for flirting to navigating jealousy and attention struggles. They explore how being overly attached to your phone can impact intimacy and connection. The hosts also tackle first date ex talk, navigating a partner’s sports obsessions, and even the quirks and turnoffs of vanity plates. Plus, Jordana shares the mix up when she confuses her husband’s favorite football team, the Jets, with the Giants. Learn more about your ad choices. Visit megaphone.fm/adchoices

10 Sep 1h 31min

In this episode, Jared and Jordana tackle dating red flags, starting with a listener’s story about a guy wearing obvious shoe lifts, sparking comparisons to push-up bras, stuffed socks, and bald men in hats. They dive into the dreaded height conversation, unpack why “short king” talk is a lose-lose, and share their own insecurities. The duo also dishes out expert advice on solo travel in their “Go Solo?” game, weighing options like hostels, group tours, and adventure spots. Plus, Jared reveals his top tips for celebrating a birthday alone, from breakfast in town to massages and movie marathons, proving that solo days can be just as indulgent and fun! Learn more about your ad choices. Visit megaphone.fm/adchoices

5 Sep 43min

Jared reveals a potential red flag: falling asleep to The Golden Girls, and yes, Betty White is involved. In this episode, Jordana and Jared break down texting disasters, from one-word pre-date replies to three-day gaps, and debate whether you’re genuinely excited to see someone or just excited to date. They weigh in on whether meeting the right person at the wrong time is actually real. Plus, they dissect the ultimate minimalist text: the dreaded “thumbs-up” emoji. Learn more about your ad choices. Visit megaphone.fm/adchoices

3 Sep 1h 30min

Kat Sadler, creator and star of the Hulu series Such Brave Girls, joins J&J on U Up to talk dating, relationships, and her chaotic personal life. She opens up about her disorganized attachment style, stories of making dates cry, and navigating love while dealing with past trauma and parental influence. From comparing the energy of New York versus London to debating whether coworker gossip is a relationship essential, Kat keeps the conversation lively and unfiltered. She also shares behind-the-scenes insights from her show and reflects on what it’s like to grow up with complicated family dynamics! Learn more about your ad choices. Visit megaphone.fm/adchoices

29 Aug 33min

From fro-yo runs in his parents’ Neil Sedaka-signed red Jaguar to unexpected parking lot meet-cutes, Jared is enjoying his Del Ray Summer. A listener shares a quirky first-date story where everyone says her date looks like Lil Dicky, and he eventually snaps! Jared and Jordana debate whether his reaction was fair or a red flag. They also tackle tricky dating dilemmas: when it’s fair to ask for a breakup refund after a partner cheats, how to date confidently with an invisible disability, and whether frugal habits in love are charming or a hard pass. Plus, they unpack a first date with an eight-year sex hiatus, weighing the context and what questions matter before moving forward. Learn more about your ad choices. Visit megaphone.fm/adchoices

27 Aug 1h 16min

Kamie Crawford is on the podcast, and we learn right away how she’s the 1% dater who found her boyfriend on the very first day of swiping! As the eldest of five sisters, she shares their collective conclusion on men and how she gives her sister's advice. She opens up about the unsettling realities of dating while Miss Teen USA and how men reacted to the title. The three also debate whether certain breakup moves are petty or justified, including Kamie’s infamous story of spitting on an ex’s belongings before giving them back! By the end, you’ll understand exactly why she calls it one of her proudest break-up moments. Learn more about your ad choices. Visit megaphone.fm/adchoices

22 Aug 48min

Jordana kicks things off by reminiscing about Billy Joel and a second date she went on, while Jared shares a story about a voice memo mishap that didn’t go as planned. In our listener emails, we dive into issues of cheating, mistrust, and an unemployed boyfriend. Jared and Jordana also dissect an “Icky or Picky?” as one listener discovers their date is a potentially full-blown Disney Adult - yep, it's a thing. Per usual the warps with the signature Red Flag or Deal Breakers covering everything from overly passionate kissers to awkward wedding plus-one scenarios! Learn more about your ad choices. Visit megaphone.fm/adchoices

20 Aug 1h 20min

This week, comedian Whitney Cummings joins J & J for a chaotic and hilarious deep dive into everything she’s done once and never again—from Ozempic to dating emotionally unavailable men. She gets into her current relationship, why she’s officially tired of mean girl energy, and her take on what makes a real friend (spoiler: they’ll tell you your outfit is trash). They also get into freezing your eggs and how men vs. women interpret toxic behavior. Learn more about your ad choices. Visit megaphone.fm/adchoices

15 Aug 1h 9min