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