U Up?

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

Jordana is on maternity leave, so Jared Fried is joined by BETCHES’ Jack Maloney to break down a second date disaster featuring aggressive tongue, a “breast exam” style titty grab, and whether bad kissing is an ick or just picky. They share exact language to use in the moment like whispering “slow down” and how to reset physical chemistry on date three. Jared tackles a listener’s breakup after a layoff where an ex is telling people she only dated him for money, and he explains why the dumper is always painted as the villain and the one text to send. Plus, they answer a vulnerable email from a trans woman who feels invisible in dating and unpack how straight men think about attraction, fear, and identity. Learn more about your ad choices. Visit megaphone.fm/adchoices

Yamaneika Saunders joins Jared Fried while Jordana Abraham is on maternity leave, and nothing is off limits. She breaks down dating at 47, hooking up with a 33-year-old Pisces, and why she refuses to “debate” her worth! They get specific about sexual chemistry, age gaps, and why synergy in bed matters more than body count. Then they tackle a 29-year-old gamer whose girlfriend hates his Fortnite obsession, a woman posting flyers to “curse” her ex in South Philly, and whether walking a kitten in a stroller is a red flag or secretly hot. Yamaneika says hot. Learn more about your ad choices. Visit megaphone.fm/adchoices

On this week's Friday Feels, Jared Freid is joined by BETCHES' own Maddie Mahoney, tackling cheating exes, pyramid scheme drama, and the first date red flags that say everything about a person. A listener discovers her ex had a secret girlfriend for nearly a year while they were together, so was getting him uninvited from a wedding petty or prudent? Then a husband asks how to tell his wife that Arbonne is a scam without blowing up their marriage. Maddie also shares her genius gift-giving hack so you will never forget a loved one's gift again! Lastly, Jared breaks down why when hearing "my life is a sitcom," you should expect them to follow up with "all my exes are crazy" and "I don't wait in lines" and end the date early. Learn more about your ad choices. Visit megaphone.fm/adchoices

Why is everyone obsessed with Heated Rivalry? Jared and his friend from the stand-up comedy world, Matteo Lane, kick things off by unpacking the hype around the viral hockey romance before diving into a chaotic round of red flag or dealbreaker. They debate whether a boyfriend kissing his girlfriend every single time she gets in the car is romantic or suffocating, react to the shock of a surprise giant tongue ring mid-dating, and argue over a man who feels “betrayed” after learning his girlfriend had a nose job at 19. The episode spirals into celebrity look-alike delusion (strong Joey Tribbiani energy), plus why everyone can’t stop talking about The Golden Bachelor! It's a modern dating drama, cosmetic surgery disclosure debates, and maybe too brutally honest relationship takes! Learn more about your ad choices. Visit megaphone.fm/adchoices

Is celebrating Valentine’s Day a basic expectation, or optional? Jared and Matchmaker Maria unpack a petty or prudent situation where a woman uses an entire couples spa gift card on herself after her boyfriend refuses to acknowledge Valentine’s Day at all. J & MM break down how attitude is everything in dating and why showing up authentically matters, especially for Gen Z. They also share what to do if you’ve been seeing someone for one day versus a few months for Valentine’s Day. Then, a listener asks how to tell a guy she wants to wait to have sex, without killing attraction, right before their first Valentine’s Day together. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is joined by original U Up? co-host Sami Sage for a fun episode that kicks off with body image, Ozempic shame, and why vulnerability isn’t owed, but it does matter. They unpack a listener’s dilemma about dating a woman who may have lost weight on GLP-1s and whether hiding old photos is a red flag, a boundary, or none of his business. Then they review texts from a guy who gives his date the ick by editing his messages multiple times, one edit should be the max! Sami and Jared also discuss what women should actually get men for the upcoming Valentine’s Day. Lastly, they dig into two red flag deal breakers: staying close with an ex-wife and being single at 33 – is that a red flag? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is joined by VP of BETCHES, Bryan Russell Smith, to kick off a Friday Feels episode that starts with a funny discussion about watching Heated Rivalry and why women are loving this show so much! Bryan shares how he met his now-husband at a bar after losing his coat, their age gap, and what Jared thinks straight dating could learn from gay dating honesty. They then dig into an icky or picky email where a listener gets dumped for loving Beyoncé, Taylor Swift, and Sabrina Carpenter instead of indie rock. Jared and Bryan answer a Valentine’s Day gift question, revealing why Valentine’s Day cookies aren’t just treats, but a way to show where someone really stands in a relationship. Finally, they answer a vulnerable email about disclosing STI on a first date, and if sharing an educational podcast is the way to go? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared welcomes Vivian Tu (@your.richbff) as the first guest during Jordana’s maternity leave, and the conversation focuses on one of the most emotional topics in relationships: money. Vivian shares why she left Wall Street, how she became a personal finance creator, and why it is important to talk about money with your partner, even on date one. They tackle a real rent divide dilemma, breaking down how splitting costs “equally” can quietly build resentment when incomes are not the same, and why a fair, proportional split matters more. They unpack a prenup panic email, where a boyfriend wants a prenup because the government already has one on your marriage, making refusal to discuss one the real red flag. Vivian also drops a hard truth: a guy can be rich on paper, but if money is all he brings to the table, he is actually poor where it counts. Be sure to check out Vivian’s new book: ⁠Well Endowed⁠, out everywhere now! Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s Jordana’s last episode before maternity leave but you can still catch episode with Jordana on their latest Benefits episodes 👉 betches.com/podcast-channel/u-up/ J&J get into emails and break down a petty or prudent dilemma involving a $20,000 “gift” from a wealthy ex and whether keeping it after a breakup is fair game. Plus, an advice email sparks a heated conversation about saying “I love you,” with age gaps 24 vs. 37, and why not all “I love yous” mean the same thing! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana is getting ready to have her twiblings, and she and Jared talk about childhood memories and how they were raised! Then they jump into emails, starting with a listener in an ethically non-monogamous relationship wondering if she accidentally sent a hookup coded message when setting up a first date. Next, they offer thoughtful advice on when and how to bring up losing a family member while dating without scaring someone off. Then they dive into an icky or picky where a listener’s boyfriend spits loogies and snot rockets on walks, is it just “man behavior” or a real turnoff? Lastly, J&J get into red flag or dealbreaker, covering dating a great guy with a kid and a difficult ex, partners who speed through 2- to 4-month relationships, and a date who picks up their plate and licks off what’s left at the end of a meal! Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are joined by celebrity hairstylist Chris Appleton, known for styling Jennifer Lopez and Kim Kardashian, to talk about hair, confidence and dating as a dad of two. Chris explains how hair can empower you, help you see yourself clearly, and change how you show up in dating and life. He opens up about his past relationship with a woman, raising children together, and navigating marriage and divorce in the public eye. Chris also shares how discovering his sexuality later in life helped him gain a deeper understanding of himself. Lastly, J&J and Chris answer a listener's question about an open relationship that’s getting difficult because one person caught feelings! Be sure to check out this episode and Chris’ new book Your Roots Don’t Define You, out now! Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J touch on the Ashley Tisdale friend-group drama and how being quietly dropped by friends feels a lot like modern dating, where things just fade out instead of ending with an honest conversation. J&J dive into listener emails, starting with a listener wondering if dating someone with zero social media in 2026 is normal or a red flag? They debate a messy breakup dog custody case in a classic petty or prudent, breaking down responsibility, fairness, and post-breakup guilt. Advice continues with how to deal with single friends who complain about dating but refuse to actually go on dates?! They end the episode with some fun red flag or dealbreaker about eating fries with a fork, to splitting a pricey bottle of wine and giving big birthday gifts too early. Learn more about your ad choices. Visit megaphone.fm/adchoices