
From fro-yo runs in his parents’ Neil Sedaka-signed red Jaguar to unexpected parking lot meet-cutes, Jared is enjoying his Del Ray Summer. A listener shares a quirky first-date story where everyone says her date looks like Lil Dicky, and he eventually snaps! Jared and Jordana debate whether his reaction was fair or a red flag. They also tackle tricky dating dilemmas: when it’s fair to ask for a breakup refund after a partner cheats, how to date confidently with an invisible disability, and whether frugal habits in love are charming or a hard pass. Plus, they unpack a first date with an eight-year sex hiatus, weighing the context and what questions matter before moving forward.
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Aug 27
1 hr 16 min

Kamie Crawford is on the podcast, and we learn right away how she’s the 1% dater who found her boyfriend on the very first day of swiping! As the eldest of five sisters, she shares their collective conclusion on men and how she gives her sister's advice. She opens up about the unsettling realities of dating while Miss Teen USA and how men reacted to the title. The three also debate whether certain breakup moves are petty or justified, including Kamie’s infamous story of spitting on an ex’s belongings before giving them back! By the end, you’ll understand exactly why she calls it one of her proudest break-up moments.
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Aug 22
48 min

Jordana kicks things off by reminiscing about Billy Joel and a second date she went on, while Jared shares a story about a voice memo mishap that didn’t go as planned. In our listener emails, we dive into issues of cheating, mistrust, and an unemployed boyfriend. Jared and Jordana also dissect an “Icky or Picky?” as one listener discovers their date is a potentially full-blown Disney Adult - yep, it's a thing. Per usual the warps with the signature Red Flag or Deal Breakers covering everything from overly passionate kissers to awkward wedding plus-one scenarios!
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Aug 20
1 hr 20 min

This week, comedian Whitney Cummings joins J & J for a chaotic and hilarious deep dive into everything she’s done once and never again—from Ozempic to dating emotionally unavailable men. She gets into her current relationship, why she’s officially tired of mean girl energy, and her take on what makes a real friend (spoiler: they’ll tell you your outfit is trash). They also get into freezing your eggs and how men vs. women interpret toxic behavior.
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Aug 15
1 hr 9 min

This week J & J dig into Jared’s hilarious origin story as a summer camper in New England, and how it still resonates with his life today. The episode kicks off with listener feedback on Jared’s ongoing Summer Dating Challenge, followed by a laugh-out-loud “Icky or Picky” that’s both “yummy” and divisive. Next, the hosts answer a listener’s question about how to date more intentionally in a world full of people still "figuring out their relationship type." Finally, J+J wrap up with a Red Flag or Deal Breakers, where they dive into travel compatibility, the chronic relationship type, and a bold move from someone handing out their number.
00:00 - Intro
13:00 - Jared's New England Camp Days
20:39 - Summer Dating Challenge
39:12 - More Is Not More
54:01 - Different Vacation Styles in Couples
#Dating #Advice #Hinge #Debate #RedFlag #Dealbreaker #DatingApps #Podcast #Summer
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Aug 13
1 hr 22 min

Jared and Jordana sit down with Sophie, who’s originally from the UK and now building her life in New York City, to unpack a long-distance love that won’t quite let go. After a whirlwind month together, she and her high school crush tried to make it work across continents, but mismatched communication styles and visa hurdles got in the way. Now he says he’s willing to wait until her “New York chapter ends,” but Sophie’s unsure if that’s romantic or just unrealistic. Is it love, pressure, or emotional limbo? They explore long-distance struggles, the tension of timing, and the culture clash between UK and NYC dating!
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Aug 8
46 min

Jared and Jordana unpack the dos and don’ts of dating in the age of social media. Jared explains why unfollowing your ex immediately after a breakup is a crucial act of self-care and shares the three things you need to consider when managing your breakup posts online. They talk about the subtle ways we use stories to check if someone’s watching and break down which ex photos to keep, edit, or delete to protect your new dating life. We also discuss a listener's question, do you need permission to follow you best friend's new boyfriend? It's a social media themed episode, be sure to listen and take notes!
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Aug 6
1 hr 20 min

Jared and Jordana are back with another movie review episode of The Materialists, directed by Celine Song and starring Dakota Johnson, Chris Evans, and Pedro Pascal. Spoiler alert!! J&J break down the film’s portrayal of matchmaking as cold and transactional, and ask whether Song set out to take down the matchmaking industry altogether. From red flag roommate situations to Coke-and-beer drink orders, J&J debate every messy decision and chaotic romance. Is it a rom-com, a satire, or something much darker?
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Aug 1
1 hr 11 min

Jordana shares her firsthand experience at a concert when she witnessed the viral moment Mr. Met fell off stage at Citi Field, breaking it down with Jared as pure comedy gold. Jared and Jordana read a listener’s email about a guy’s shy hopscotch move on a first date and debate when quirky crosses into “icky.” They dive into a friendship dilemma about hooking up with a best friend’s college fling years later, exploring honesty and boundaries. Plus, Jared calls out the major red flag of guys asking for selfies before the first date: “If a woman asks me for pictures, I’m opting out.” This episode covers hilarious fails, dating deal breakers, and navigating complicated friendships!
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Jul 30
1 hr 13 min

Dating in your 40s? Jared and Jordana break down why it actually gives you the upper hand, less game-playing, more clarity, and faster exits from the wrong situations. A listener writes in about a promising new connection and a big reveal, prompting a convo on knowing what you want as you get older. Then, they react to a jaw-dropping first-date horror story involving a drunk, naked sleepwalker and a ruined mattress. The debate continues: is peeing the bed a dating red flag... or just a funny story? Modern dating, relationship boundaries, and chaotic hookups, this episode has it all! full ep here 👉https://youtu.be/wOrL4kV0bSQ
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Jul 25
35 min
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