U Up?

Merry Christmas Eve from your friendly elf and what seems to be Jared as sexy Santa? Jared talks about a potential gym flirting moment that leads into a deeper conversation about dating burnout, emotional self protection, and why avoiding risk can start to feel safe but sad, with comparisons to Leonardo DiCaprio style dating rules. They break down listener emails about bringing a boyfriend of two years to a family Christmas party, asking when it is actually the right time to include your significant other in family holiday gatherings. J&J read a petty or prudent about getting Christmas ornaments back, an email about a gifting fight over a valuable sentimental book, and multiple fed flag or deal breaker stories involving Christmas cheer, cultural gift rules, and whether believing in Santa at 21 is sweet or concerning. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared celebrate the holidays by sharing gift ideas, including Jared’s new book, Walking Red Flag, which we suggest pre-ordering! Next, a listener asks J&J to weigh in on whether her date’s bragging about delaying climax is an icky moment or just being picky. They answer a question about giving a boudoir photo shoot as a Christmas gift and how it can boost confidence. Would you do a sexy photo shoot for your loved one?? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana kick things off with a little holiday gift exchange powered by Uber Eats, proving last minute gifting doesn’t have to be stressful! Then they tackle a big dating etiquette question: you book a trip together, break up, and suddenly you’re stuck with the bill - do you still split the bill? They then get into an icky or picky where a listener asks if her boyfriend’s top Spotify song of the year being his own, cringe or just a harmless quirk? Lastly, they get into some red flags: a married grown man sharing an Amazon account with his mom, and a boyfriend who still won’t show his apartment after four months of dating! Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on U Up?, Jared asks Jordana if when seeing an ex posting on social media can still hit harder than it should. They celebrate being named to Spotify’s Best Podcasts list, share Jared’s upcoming stand-up plans, and unpack his tradition of spending New Year’s alone. They dive into listener emails, including one about a gifting dilemma with someone who doesn’t celebrate the holidays, sparking a debate on what’s appropriate when you’re casually dating, in a segment sponsored by Uber Eats. Also, they unpack an icky or picky” email that asks whether nonstop talking and essay-length texts are a real ick or just part of modern dating? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared shares a hilarious story about being approached by Hannah Berner’s cousin, including a moment where he is told to look less “miserable” during a mid-Florida night out. They share fun family memories, and Jordana recalls Lindsay Lohan’s BETCHES cameo that was a highlight this year. They then get into listener questions and debate how old is too old to play video games and why it is frustrating when your partner hides their hobby. Next, they tackle an “icky or picky” scenario about a date who brought an overnight bag, which is thoughtful but a little presumptuous. J&J also weigh in on red flags versus dealbreakers, including staying friends with an ex, unsolicited critiques about your apartment, and being asked to pay for a date at the last minute. It is a fun episode you do not want to miss! Learn more about your ad choices. Visit megaphone.fm/adchoices