Jared fills Jordana in on his bizarre and funny late night Halloween experience and they also discuss the new Martha Stewart documentary. They hear from a listener who is struggling with communication from their partner. Next, they hear an Awkward Encounter that ends with them walking in on somebody in bed with another girl. Then, they discuss an email from a listener who isn't sure how to know if a relationship is serious if they both don't want marriage. Finally, they dive into a round of "Red Flag or Deal Breaker?" featuring a fat-phobic date, a boyfriend unwilling to compromise, and Olivia Rodrigo's number one red flag.

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DISCLAIMER: This episode was recorded prior to the election. Jared and Jordana divulge the complexities of dating during an election year and how to navigate discussing politics on a date. In this week’s "Icky or Picky?" a listener wants to know if their date littering dog poop is something worth overlooking. Next, they tackle a listener’s dilemma concerning her date's disappointing "whiskey dick" and Jared opens up about male performance anxiety.

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We're officially headed towards the toughest times to date—cuffing season and the holidays—so Jared and Jordana discuss how to navigate this tricky period. They hear from a patient whose attractive doctor makes her temperature rise but she's unsure whether to make a move or not. Next, they hear an Awkward Encounter about life at boarding school. Then, they discuss an email from a listener whose boyfriend is extremely jealous and suspicious of her male friend. Finally, they dive into a round of "Red Flag or Deal Breaker?" about toilet plungers and gift giving etiquette.

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Jared and Jordana break down artist Spritely’s viral TikTok breakup video, unpacking relationship red flags, communication pitfalls, and the complexities of moving for love. In this week’s "Icky or Picky?" a listener asks if designer labels make or break a date J&J agree, no one should feel judged for their fashion choices, no matter the brand. Next, they tackle a listener’s dilemma about tracking down a Bumble match from nearly a year ago. Is her search romantic or just plain extra? Jared and Jordana empathize but offer a crucial reminder: while bold moves can impress, more than one follow-up message might push things into red flag territory.

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It’s the spookiest episode of the year, and Jordana and Jared are feeling a little trapped in more ways than one! They rank Halloween couple’s costumes for 2024 and explore what your costume choice reveals about your relationship. Then, they tackle a listener’s costume conundrum, where differing opinions on what’s “too sexy” lead to the conclusion that her date is too controlling. Next, an Awkward Encounter that’s more alarming than amusing. Then, they advise a listener who wonders if she’s being unreasonable for expecting her Halloween one-night stand to leave by morning. J&J completely understand her perspective and hold a masterclass on how to nail the perfect one-night stand. Finally, the episode wraps up with a Halloween-themed lightning round of “Red Flag or Deal Breaker,” tackling controversial costumes, costume refusals, and the right time to suggest a couples costume.

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In this Friday’s episode, Jordana navigates the chaos of her impending move, sparking a deeper conversation with Jared about how our living spaces impact relationships. Next, they tackle an Icky or Picky from a listener overwhelmed by her boyfriend’s bombardment of romantic texts. Even though this partner checks all the right boxes on paper, J&J explore why it’s okay to walk away when the spark just isn’t there. Finally, they dive into an email from a listener seeking advice about her boyfriend’s hidden vaping habit, which was downplayed early on. J&J encourage an open conversation that leans into support, not shame—proving that honesty is key.

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Non-subscribers, take note: new episodes will now be dropping every Wednesday and Friday at 6 AM EST. Now that business is taken care of, there's a trending breakup J&J need to discuss: Jason Tartick and Kat Stickler. They analyze their breakup announcements, plus discuss societal pressures and expectations put upon celebrity couples. Next, a 31F is having trouble with same-day date cancellations, leading J&J to explore the nuances around when and how to cancel on a date. Then, brace yourself for an Awkward Encounter about a college kiss gone horribly wrong—it still haunts our listener to this day! The second advice email is seeking a masterclass in becoming a more effective PITA (Pain In The Ass). J&J delve into the importance of negotiation in relationships and wielding strong opinions as an advantage. The episode wraps up with a round of “Red Flag or Deal Breaker,” about a surprising pet, a boyfriend who selectively shares, and a date who insists on getting all the cash back.

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Welcome to the inaugural Friday episode! Jared and Jordana are still at Spotify HQ, gavels in hand, ready to tackle Couple's Court. This week, they dive into a sh*tty dilemma from a listener who's struggling to get her boyfriend to clean up his bathroom blow-ups. Jordana passionately sides with the listener, while Jared shares how we can do better as a country when it comes to bathroom supplies. Next, a 30F listener without social media feels uneasy that her 32M boyfriend—who posts frequently—has no pictures of her on his feed. Is it weird that he's leaving her out of his posts even if she was there for those moments? J&J give her tips on how to address the issue with a vulnerable approach instead of an accusatory tone.

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This week, J&J are coming to us from Spotify HQ, and Jordana is realizing she doesn't know NYC as well as she thought. First, they tackle a listener's email about men on dating apps giving her unsolicited advice. J&J discuss how to nail the art of roasting without going off the rails. The Awkward Encounter is a two-parter including a train platform romance gone wrong. Then, another listener needs help validating jealousy after her fiancé shares a compliment he got from a coworker. J&J try to give her perspective and decide if couples should even be sharing the compliments they receive outside their relationship. The episode ends with a round of “Red Flag or Deal Breaker” about a pocketed dirty condom, a mom with a vendetta and a light show at 3 AM.

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Jared and Jordana kick off this last Sunday Special with a round of “Petty or Prudent?”. They tackle a homemade sign a listener hung in her neighborhood, calling out her ex for his deceitful ways. It’s her bold move to retaliate against a liar and cheater, but J&J have some clever suggestions for delivering her message with a bit more finesse—no neighborhood drama required. Next, J&J give advice to a listener whose boyfriend is still grappling with the emotional fallout from his recent divorce. Despite their amazing adventures and great chemistry this couple might have, J&J focus on the passive aggressive ways he has been downplaying their relationship and wonder if he’s even ready for someone new.

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