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?

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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.

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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!

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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

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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.

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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!

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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!

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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!

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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.

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Jordana and Jared hang in Florida and we hear about it on today’s ep! Jordana shares what no one tells you about traveling with twins, including getting interrogated by strangers about her fertility journey, making up fake answers about how many minutes apart the babies were born! J&J get into listener questions and debate whether divorced parents should still take family photos together at a Sweet 16, unpack a chaotic breakup revenge post asking for “female references” before dating men, and decide if a man secretly liking his own Instagram posts from a finsta is a red flag or just deeply embarrassing! Plus, they break down the most unhinged first date confession ever: a guy casually calling porn “documentaries.”

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