U Up?

Esther Perel is back to join Jordana and Jared to talk about AI girlfriends, if using AI to write a love letter is dishonest, and the real reason we are choosing our phones over in-person connection. J&J and Esther talk about friendship breakups and whether going to therapy with your friend will help. Plus, we get Esther Perel’s take on chores in the home. Does she end up agreeing with J&J’s dating advice?! Learn more about your ad choices. Visit megaphone.fm/adchoices

This week, J&J learn that Hinge is banning screenshots, and they question whether this is good for dating or helps cheaters get away with it! They Jordana and Jared see a man who posted his divorce announcement with a thoughtful, brief FAQ and discuss whether all breakups should have posts like these. They then discuss if it’s weird to keep a list of everyone you’ve slept with, whether single friends should be invited to couples nights, and if it’s petty to refuse to treat your ex’s new baby. Lastly, they discuss being compared to an ex by your husband’s family and how many football leagues are too many to be apart of?! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana are learning about Instagram’s new blur feature for “soft launching” couples in their new segment, Are U Up to Date? They then answer a listener’s email about asking for an engagement ring back after years of marriage and whether it’s petty or prudent. Lastly, they help an unsure listener who doesn’t want a second big wedding, but her new fiancé, who has never been married, wants a big wedding to celebrate his family’s Chinese wedding traditions. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared are reading through a listener’s breakup texts, and the list of reasons to end it is long! A cozy cabin weekend in the woods was not as romantic as she thought, with complaints about restaurant choices, what time to go to the farmers market, and feeling judged for her kinks. J&J also get into the latest dating news, from Margot Robbie taking her husband’s last name after nearly 10 years of marriage to a $10 NYC dating photo booth that matches strangers using question surveys. Lastly, they get into family-related red flag dealbreakers, including a boyfriend who texts his girlfriend’s mom, a family that keeps the TV on all day, and if refusing to try your partner’s mom’s food is a dealbreaker. Learn more about your ad choices. Visit megaphone.fm/adchoices

Heather McMahan joins Jordana & Jared to talk about living with her mom after becoming a newlywed and getting fired from the Ryder Cup! She talks about how meeting her husband in a gay bar made her feel love at first sight, and she shares her direct advice on how to pick a life partner! Lastly, they help give advice to a newly married couple with a baby on how to navigate living with their parents while being new parents themselves! Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s a rapid fire episode with 10 relationship questions from YOU, the listeners. Jordana and Jared answer questions about how long is too long to go without sex or a marriage proposal! They discuss whether high-drama baby mamas are worth it long-term, how to split chores at home, and how to combine finances. They also discuss trips, from honeymoons to splitting visits with the in-laws for the holidays, and how both can be stressful to plan! Lastly, they get into relationships outside your marriage and whether you can come back from emotional cheating or not. It’s a spicy rapid fire episode you don’t want to miss! Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s autumn, and Jordana & Jared are challenging their listeners to put down their phones, get out of the house, and talk to people! They then get into questions from you and decide if secretly hiding your partner’s ugly clothes is petty or prudent. Or just helpful?! Lastly, they help a woman decide whether or not to make a move on a guy 7 years her junior. Does age really matter? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana discovers her husband used an AI chat to help him write her birthday card, and she has some feelings about whether a love letter still counts when chat gpt edits it for you! Jared and Jordana then get into listener questions, answering a woman who found her husband texting an ex, whether busking on NYC streets is a red flag, and whether asking for a number before a date means something or if it’s okay to keep the chat on hinge. They also discuss Jared’s comedy special and how getting a message from David Schwimmer, yes, Ross Geller, was a career highlight! Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana tells Jared how her vacation ended up being the busiest and most unrelaxing, but also the most fun, due to Ronnie the dog getting kicked out of boarding for peeing and joining the family’s chaotic Montauk trip! They then get into listener emails and discuss whether a partner should wait in the regular TSA line, what actually marks the end of the honeymoon phase, and whether small gestures like Trader Joe’s flowers matter more than big romantic moves. They also talk about a passionate “lake life” man who may have used his love of camping as an excuse to break up, and whether a fantasy football draft on your wife’s birthday is a red flag or deal breaker. We say yes! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana discovered that you can crash a wedding and think it’s the best way to spend a night out with someone you’re dating! From black-tie dress codes to open bars and live bands, it’d probably make the best eighth date. They also advise a listener to take a break from dating apps after he starts analyzing whether his spontaneous Bumble date will make a good mother. Too soon, buddy! Lastly, they discuss the awkward conversations that come with financially relying on your partner, including budgets, joint savings, debt, and what happens if you break up. Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s Jordana’s birthday, Happy Birthday, Jordana! J&J debate wedding plus-ones, jealous partners, and how much texting is too much when you’re dating. They also dive into a text thread discussion of a boyfriend fangirling over a professional tennis player and his girlfriend is getting the ICK! They then discuss if it's a red flag for a woman who spends five nights a week at salsa class, and whether you should stay friends with someone you cheated with! Learn more about your ad choices. Visit megaphone.fm/adchoices

Lauren Lapkus joins Jordana and Jared to talk about dating actors, marriage, kids, and whether being good at acting makes someone too good at lying?? The three play red flag or deal breaker, asking Lauren on everything from an ex’s wedding dress to bad breath, Disney adults, and having a sexual fantasy about your date’s famous character! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared shares about meeting his girlfriend’s friends, how he got questioned about his phone use, and how being in a relationship means meeting the friend group! Then J&J discuss how men really feel about losing a partner, how they would go about life after a partner’s death, how often your spouse should visit your grave, and whether remarrying too soon should get you written out of the will. They also discuss a husband lying about buying his ex a gift, stalking an ex’s IG stories, Disney Adult red flags, asking someone if they had a good time on a date, and whether shutting off your apartment’s electricity is a red flag or a deal breaker. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared watch a TikTok of a groom zip lining into his own wedding and debate whether a groom spending $24K is a major ICK. They then answer a question from a newly single mother who is nervous about dating again, and they call Jordana's mother! Jordana's mom is a gynecologist who has dated after divorce and raised 8 kids, and gives a lot of great advice this episode about getting back into dating, talking about your kids with your date, feeling confident and sexy again, and why a date should feel like a chance to get out of mommy mode! Plus, Dr. Lisa Rosenberg gives some VERY candid advice about keeping things fresh down there! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared discuss a dating app match who canceled a first date after there was a lull in texting and then sent practically a full dissertation explaining his communication style as if his date was in the wrong for not knowing. J&J also answer whether wearing an ex’s gift years later means you’re still thinking about them, if a co-ed bachelor party where partners aren’t invited is petty, and whether a filthy apartment is an instant deal breaker! Also Jared shares how he shares his upgrade on a flight with his girlfriend instead of taking it for himself – growth!! Learn more about your ad choices. Visit megaphone.fm/adchoices

It’s a Friday Feels episode and J&J are questioning, "would you pay $5,000 to break up with someone"? The two then get into listener questions and discuss whether it’s petty or prudent to ask for your shared spicy toy back after a breakup. They also read a question from a single woman who is searching for a sperm donor to have a child and was surprised when her married male friends offered their own – without consulting their partners!?! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared discuss what to do when your friend starts dating your crush, whether the way you handle getting roasted at a comedy show is an ick, and how to handle overbearing in-laws. They also talk summer dating, waiting for your partner at the airport, and using AI to write a prenup. Also Jared has a new Netflix special, The Family Plan, coming September 1! Add to your queue today! Learn more about your ad choices. Visit megaphone.fm/adchoices

Harry Jowsey joins Jordana and Jared to talk about how he was engaged to 20 women at once for his new Netflix’s show, Let’s Marry Harry, what changed for him after losing his father and why dating is harder when it's played out on social media! Harry weighs in on listener questions where the guy asks for a first-date ultimatum and whether it’s ok to date multiple people at once, and why he’d rather text than call someone for a breakup. We learn a lot about Harry and how charming he is and why you should watch his new show! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared debate whether it’s okay for your boyfriend to go on a trip with his ex, especially when they still own an apartment together. They also decide if an ex was petty for showing his former girlfriend the engagement ring he bought for her, and whether a bad first kiss is enough to end a great date. Plus, they talk fanny packs, tasting-menu dates, and why some couples get engaged without planning to get married. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared opens up about a fear of his when getting serious with his partner, figuring out how to balance love, family, and a career that keeps him on the road. Then J&J debate whether a husband should text his ex happy birthday and solve a bride’s very specific $10,000 wedding dress wedding night dilemma! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared get a visit from Jordana’s brother, Jon! He joins to pick up a toothbrush but ends up talking about dating in San Francisco, why he wants more banter and “relational chaos,” and whether Jordana can help him find a girlfriend. Then J&J play Second Date Yay or Nay after a three hour brewery date ends with a guy asking if a woman’s birthmark is an allergic reaction. It’s giving Nay. Also, Red Flag or deal breaker: your boyfriend refuses to like your IG post? They also discuss whether a boyfriend should offer to help when his girlfriend is overwhelmed by a new golden retriever puppy! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared discuss a petty or prudent and whether a brutal Costco-inspired rejection text was justified? They discuss what singles mixers are really like and why SIMPLE first dates usually beat elaborate plans! They then help a listener who feels like the only single person at every wedding, sharing advice on surviving the wedding season, finding more single friends, and stopping the comparison trap. You have to find your people! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared are back talking about what it means to feel successful, happy, and “content” while still chasing the next big thing! They break down the confusing world of dating labels after a Love Island conversation about situationships, exclusivity, and when someone is actually your boyfriend or girlfriend. Plus, they answer listener questions about a date who sent a questionable outfit text, whether to expose a cheating ex, and what is a dating “ick” and what is actually a deal breaker. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared calls his parents with some BIG news about a very important award, and you won't believe their guesses! Then, Jordana and Jared get into listener questions, breaking down a woman posting flyers about her ex all over Indianapolis in the Are We Dating The Same Guy Facebook group, and a new website that only reconnects exes if they secretly choose each other. Would you try to reconnect with your ex on a dating app? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana are talking about kids and whether Jared would actually make a good father, since icky things don't seem to phase him! Jared encourages people to be present this summer, delete the dating apps, and get outside. They then get into a listener question about hanging out with your in-laws: do you need your spouse to be there to spend time with your mother-in-law? Plus, they tackle some Red Flag or Deal Breakers, including never making your bed, co-parenting a dog with your ex, and a date who asks you to bring Adderall! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana begin today’s Friday Feels by talking about the viral memoir Strangers and why breakup books hit differently than breakup TikToks! They reminisce about their fully remote recording days and how pandemic dating advice was really different and its own time vault. J&J get into your dating questions, answering a petty or prudent: reporting your cheating ex to his college professor, and also can you rebuild trust after years of secret dating apps and lies? Sometimes searching for answers can keep you stuck in the wrong relationship! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana are in the studio talking about their morning commute, which was delayed due to Taylor Swift’s Madison Square Garden wedding! They kick off today’s episode with Who's Your Hall Pass? Dua Lipa did not make Jared’s list! Then J&J continue with questions from you and have a Summer Lightning Round of dating questions, debating the right time to have the exclusivity talk, whether unmarried couples should send holiday cards, and after how many dates breaking up over text is no longer okay. They also discuss how to initiate a first kiss after five dates with no kiss and whether dating someone with different political views can actually work. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared’s Netflix special is coming out in the fall and he recalls a roasting bit with Rob Lowe, and why meeting him completely changed his mind. J&J then debate whether it's petty or prudent for a guy to text his ex that he won a $50 competition just one week after dumping her. They also unpack a breakup over indefinite travel, questioning if it’s a right guys, wrong time moment? They discuss why women convince themselves they'll never find another great connection, and Jared's rule that you should never say "you" in a breakup! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana debate whether dating a diehard Philly’s sports fan is a harmless quirk or a real relationship problem. Can passion be just plain obnoxious? They also unpack the internet debate over women proposing to men, why Taylor Swift rumors about an MSG wedding sparked such strong reactions, and reminisce about the glory days of Fire Island share houses after college. J&J also discuss first date bill split etiquette: it's not really about the money, it's about the communication. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared and Jordana are getting ready for Fourth of July weekend, where Jared will be staying with Jordana, finally! Then Jared shares the funniest wedding guest he's ever met, a guy with Oakleys on the back of his head who somehow became the life of someone else's wedding. Plus, they debate whether sending a hotter guy to pick up your stuff after a breakup is petty or genius, and help a listener whose future in-laws keep letting themselves into the house, cleaning, dog-sitting, and crossing every boundary imaginable. It's an episode about weddings, breakups, overbearing families, and why sometimes "helpful" can go way too far. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is back from his book tour convinced dating is rougher than ever, and he and Jordana break down why so many singles are feeling burnt out. Then they tackle whether asking for someone's Instagram or Snapchat before a first date is a hookup red flag, if you should reply when an ex apologizes 12 years later, and whether all men over 40 on dating apps deserve the bad reputation. Plus, is it fair to ask your boyfriend to wear pants around the house, and does living together "feeling like a vacation" actually mean you're not being taken seriously? It's a packed episode full of dating hot takes, relationship debates, and the kind of questions every couple will end up arguing about. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared shares the wildest piece of weight loss advice he's ever gotten from a fan at a country club, leading to a discussion about criticism, internet comments, and why the people who care enough to complain might actually be your biggest fans. Then, J&J debate whether it's an ick or just being picky when a hinge date pulls out a Bible app and reads a favorite verse at a dive bar over chicken salad sandwiches. Too passionate? Later, a listener discovers her boyfriend secretly asked ChatGPT if he should break up with her and finds a list of complaints about her! Is using AI as a relationship therapist a red flag, or is reading someone's private doubts the real problem? J&J have some thoughts! Our last email was originally inspired by Lindsey Hall's Substack, I Stumbled Across My Boyfriend's ChatGPT and It Ended Our Relationship Learn more about your ad choices. Visit megaphone.fm/adchoices

The Knicks' recent success is creating a wave of new fans, and Jared explains why sports foster community, connection, and shared experiences, while Jordana compares it to the passion people have for Bravo and reality TV. Then J&J tackle one of adulthood's biggest questions: how do you know if you actually want kids, or if the DINK life is right for you? Plus, they debate a dishes-related relationship standoff, unpack the emotional fallout of being ghosted after a great Hinge date, and ask whether an out of town wedding invite on date five is romantic or a major red flag. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana risks a parking ticket after creating her own train station parking spot, while Jared celebrates a glowing dentist report and shares why his gums are finally growing back. Then J&J debate whether a hinge date carrying a gallon jug of water everywhere is an instant ICK or just a dedicated hydration habit. They also discuss how GLP-1 medications are changing modern dating, from awkward dinner dates where you barely eat to deciding whether you should tell someone you're taking it. Plus, Jared opens up about his own GLP-1 experience, weight loss, food noise, and waiting to find out if Walking Red Flag made the New York Times Bestseller list!! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is officially OVER hearing himself talk after weeks on his book tour, but appreciates all the great feedback from fans who have read his book. J&J get into listener questions, reacting to a woman who discovers her fiancé secretly messaging his ex through a shared Notes app, leading to a conversation about “open phone policies” and whether they’re ever a good sign. Later, they tackle an icky or picky about a 32 year old fiancé who wants dinner with his parents four nights a week (or more), and a red flag or dealbreaker involving a date who may have gotten a little too excited from a simple touch on the couch. Learn more about your ad choices. Visit megaphone.fm/adchoices

Summer is finally here, and Jared and Jordana are feeling the relief after what felt like New York's longest winter. They dive into the realities of parenting twins, why single parents deserve way more credit, and the surprising story of Olympic champion Alysa Liu's father choosing surrogacy and solo parenthood. Plus, Chelsea Handler publicly calls Bobby Flay a bad date after he ordered room service and left her with the bill, sparking an "Icky or Picky" debate. Then, a listener's daughter's serious boyfriend says he's "all in" but refuses to meet the parents. Is it normal after a recent divorce, or a red flag? Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared recaps his Kelly Clarkson appearance, the launch of his new book, and why seeing your book in an airport might be the ultimate career milestone! J&J then unpack listener questions: a first vacation to Morocco that had daily sex but zero "I love yous," and debate whether a romantic getaway can reveal a deeper compatibility problem. They also tackle an icky or picky about a gym guy who put his number directly into someone's phone, plus a relationship dilemma involving a boyfriend secretly working nearly 80 hours a week between his regular job and Home Depot. And yes, things somehow end with a debate about men's underwear, Simon Cowell, and whether couples who "never fight" are actually communicating at all. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana opens this episode with a question for Jared: do some men really think parents find out they’re having twins at the delivery room? That kicks off a hilarious conversation about prenatal care, “punch bowl” movie myths, and just how little some people know about pregnancy. Then J&J debate whether reporting your ex-fiancé’s Facebook profile picture (featuring YOUR dog) is petty or justified, and help a listener stop spiraling after discovering her boyfriend’s Stagecoach cheating scandal. Jared also shares why he avoids hot takes, talks about his upcoming book launch, and reveals his very specific pool temperature requirements for his visit at Jordana’s! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared is packing a tux for a black-tie-optional wedding, which leads to a debate about plus-one etiquette and who should pay for the wedding gift when you're newly dating. Then they discuss a listener’s theory that the best place to meet men is a Wednesday night bowling alley and introduce Jared’s Summer Strut Challenge: 12 walks in 12 weeks to grow your dating network through friends and family! They then break down whether excessive exclamation points and smiley faces are actually an ick, plus a tough question about dating someone who talks about marriage but never makes you feel cared for. And in Red Flag or Deal Breaker, they cover being compared to an adult star, getting discovered through a viral TikTok crush post, and farting in relationships. Check out Jared's new book! 👉 Order Walking Red Flag: Dating Advice from Your Favorite Guy Friend Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J get into a recent article where they mention dating has become a luxury in 2026! From $20 coffee dates to the hidden “pink tax” women pay just to get ready, maybe it really is too expensive to date these days. Then they break down Bumble’s new AI matchmaker “Bumblebee,” why Jared thinks dating apps are just slot machines for lonely men, and whether AI is making modern dating even more fake. Plus, an “Icky or Picky” email about a college guy admitting he masturbates to a match’s profile photo sparks a surprisingly nuanced conversation about dating expectations, sexual honesty, and learning how to date in your 20s. Later, they unpack a marriage conflict years in the making after a husband still hasn’t read his wife’s wedding vows, and why “testing” your partner instead of communicating never works. Learn more about your ad choices. Visit megaphone.fm/adchoices

This week J&J unpack why lying in a relationship can be worse than cheating itself and debate whether an ex warning a new girlfriend is “helpful” or completely unhinged. They break down a breakup that left one listener scrambling for a new apartment and explain the difference between being petty and being prudent when money and resentment collide. Plus, Jared defends his longtime 'finger in the butt' stance while Jordana gives practical advice for couples trying new things in bed without shame or panic. They also discuss a man who refuses to wear deodorant (red flag), a fiancé calling another woman “the prettiest girl he’s ever seen,” and Jared accidentally discovering he’s been saying “sight on scene” instead of “sight unseen” for years! Learn more about your ad choices. Visit megaphone.fm/adchoices

This week J&J welcome Dr. Orna Guralnik from Couples Therapy to talk about the biggest mistakes couples make before they ever step into therapy! Dr. Orna explains why “agree to disagree” is usually just code for “I’m exhausted trying to change you.” The conversation gets hilarious when Jared roleplays a full couples fight about chicken vs. steak dinner and accidentally reveals his deepest relationship fears. Plus, Dr. Orna shares the biggest sign couples therapy is happening too early, the moment it’s officially too late, and why respecting your partner’s differences matters more than ‘winning’ the argument! Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordana and Jared are judging Mother’s Day Instagram tributes like they’re relationship crime scenes. And honestly, some of these captions are screaming “save the marriage post!” They debate whether a woman should warn her ex that she’s pregnant with her new boyfriend’s baby, discuss a first date where a guy ate a pastry and drank coffee in front of his hungry date, and debate over whether sending a nostalgic middle-school boyfriend photo is sweet or secretly flirty. They also tackle a missing-front-tooth dating dilemma, a possible hoarder girlfriend, and a man who told his live-in girlfriend to move out for a month so he could “work on his mental health.” We think this relationship is doomed! Learn more about your ad choices. Visit megaphone.fm/adchoices

J&J are joined by Samantha Wynn Greenstone and Jacob Hoff, the married couple behind the “I Married A Gay Man” podcast, to unpack the relationship dynamic that has the internet completely fascinated! They tell their story of meeting during a Fiddler on the Roof audition, becoming inseparable best friends, and the text message that changed everything after an energy healer told Samantha they shared a “spiritual umbilical cord.” Jacob opens up about identifying as gay while being deeply in love, monogamous, and raising a baby with Samantha, while the group dives into why labels, attraction, and soulmate connections don’t always fit into neat boxes. Learn more about your ad choices. Visit megaphone.fm/adchoices