U Up?

Jared is officially meeting his girlfriend’s parents, but what should he bring? J&J break down the strategy of what to bring, expectations of meeting the family, and what actually matters during that first intro. Jared and Jordana get real about long distance dating, traveling for a relationship, and how to set boundaries when your partner joins you on work trips. They also unpack a listener’s “OnlyFans comment” nightmare after a first date setup goes sideways on Instagram. Plus, Jared explains why asking for Instagram instead of a number is a major red flag! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana is back after maternity leave with twins (AKA “Twisters”), and she and Jared finally catch up on everything! The two get into the What Are You Up To? segment brought to us by HBO’s Euphoria. Jordana shares life with newborns and how her relationship with Mike has changed, from couples therapy to what actually matters in a partner once you have kids. Jared drops a major update: he has a girlfriend! They originally met at the Comedy Cellar, dated years ago, we hear how they decided to date again! Plus, they get into some fun red flags or dealbreakers: debating whether not asking about a sick cat is a dealbreaker, how much you should tip on a $45 date, and why trying too hard, or not at all, might both be red flags!! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is joined by the hilarious Emma Willmann for the final episode with a guest cohost! They break down a relationship where a boyfriend won’t stop correcting his dyslexic girlfriend’s grammar and why that might actually be a deal breaker. Jared shares a wild DM involving a “dead grandma date request,” leading to one of the strangest fan interactions he’s ever had. Lastly, they get into a listener being judged for kissing her friend while questioning her sexuality. Jared and Emma get into all your dating questions and more! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared Freid sits down with Tiff Baira to learn all about Street Hearts, how to flirt with men and the best place to break up in NYC. They dive into listener dilemmas about how to turn long, flirty bar conversations into a real first date, and what to do when you are stuck in “Instagram limbo” after making the first move. The conversation also gets into major “ick” territory, including mouth open chewing, loud talking on dates, and whether sensory triggers like misophonia are real dealbreakers or just being too picky. The episode wraps with a funny “Petty or Prudent” game featuring a breakup, a questionable shower head theft, and post-relationship revenge etiquette! Learn more about your ad choices. Visit megaphone.fm/adchoices

Comedian Ashley Gavin joins Jared to talk about dating, sexuality, and the chaos of life on the road! Ashley explains her open relationship rules with her girlfriend, their monthly check-ins, and how touring sometimes leads to unexpected hookups. They tackle listener emails about bisexual curiosity blowing up a relationship and whether a 35 year old with a roommate should be a concern? Plus, Ashley shares what life on the road is really like, from asking a hookup to put her knife away to fans having unexpected coming-out moments at her shows. It’s a fun episode where we learn all about the Gavin Method!! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is joined by Hinge relationship expert, Logan Ury, to break down some of the biggest dating questions listeners are dealing with right now. They debate whether asking for a voice note before a first date is an innocent preference or a major red flag, and unpack the idea of “digital body language” when someone is great in person but disappears over text. They also dive into the classic “right person, wrong time” debate and the Sex and the City taxi-light theory of commitment. Also, one listener wonders if dating in NYC has become impossible thanks to hyper optimized schedules full of cold plunges, pilates, and skincare routines. Is it selfish or self care? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is joined by BETCHES’ own Tess Tregellas for a hilarious Friday Feels episode. Tess shows up with a positive attitude but she does reveal she just learned sad news about her childhood dog. But quickly turns the mood around as they dive into listener dilemmas! They debate whether calling your fiancée a “solid 8 out of 10” is a red flag or a relationship killer, and explore why words like “pulchritudinous” are far superior to numbers when describing your partner. Later, the two help a listener spiraling about moving in with her boyfriend in NYC, covering anxiety, overthinking, and why sometimes you just have to be excited about love! Plus, Tess shares the wild story of meeting her boyfriend while wearing a wedding dress! Learn more about your ad choices. Visit megaphone.fm/adchoices

This week on U Up?, Jared is joined by Aleen Dreksler, CEO and co-founder of BETCHES, for a chaotic and honest deep dive into mama drama, ex etiquette, and career vs. kids debates. They discuss boundaries with mother-in-laws and what you can negotiate versus when you should just say nope, covering everything from holiday turf wars to posting your baby on Instagram without permission. Then it’s petty or prudent when an ex crashes a run club and sends a seriously annoying “it’ll get easier over time” text. Plus, an Icky or Picky ruling on a second date who announces a strict “no phones at the table” policy like he’s running a dictatorship. Be sure to not miss updates from Jordana! 👉 https://subscribe.betches.com/u-up-with-benefits Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is joined by Dr. Naomi Bernstein of the Oversharing podcast to unpack dating after divorce, performance anxiety, and whether taking intimacy slow signals emotional baggage. They break down an email from a 34-year-old woman dating a gentle, recently divorced man who says something “deeper than biology” is blocking intimacy. Then they debate if a flight attendant was right to tell a 30-year-old guy he’s “too nice for casual dating.” Plus: performance anxiety, people pleasers, alpha vs beta energy, and why sexual chemistry doesn’t always match long-term potential. Jared and Dr. Naomi get deep and at one point, when Jared asks Dr. Naomi to give him real advice about his own dating life! Learn more about your ad choices. Visit megaphone.fm/adchoices

Bob the Drag Queen and Jared kick off today’s episode bonding over their favorite WWF wrestlers and swapping stories from their early stand-up comedy days. Then they dive into modern dating drama, including a straight boyfriend who wants to explore drag, but his girlfriend is feeling insecure and unsure how to navigate it. They red flags, deal breakers, and quirky relationship moments, from mannequins at the front door to reality TV obsession. Bob talks about having two boyfriends and advises an emailer that dating an ENM man is a definite dealbreaker if you’re monogamous at heart! Along the way, Bob shares stories from Eddie Izzard, Harry Styles, Moulin Rouge, and life on stage. It’s a fun episode you don’t want to miss, and be sure not to miss Bob on Broadway until March 22! 👉: https://www.bobthedragqueen.com/appearances Learn more about your ad choices. Visit megaphone.fm/adchoices