Coffee and Cleavage

• She Cheated With My Roommate 😱 Worst Date Stories Ever

  In this episode of Coffee and Cleavage, hosts Lynnie, Shantal, and Gary explore three listener-submitted dating disasters. First, a caller catches his girlfriend of seven years in bed with his roommate and wonders how to trust again. Next, a man’s relationship—born from a “take one for the team” favor—faces insecurity after a friend’s careless joke about attraction and weight. Finally, an app date ends with a lecture about who should pay and what counts as “effort.” 

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  18:40
• Monogam-ish Madness 😳 Hall Passes & Threesomes

  In this episode of Coffee and Cleavage, hosts Lynnie, Shantal, and Gary explore relationships that are “not quite open, not exactly closed.” They debate whether hall passes protect commitment or plant resentment, how couples negotiate soft-swap vs. full-swap boundaries, and whether emotional monogamy can survive sexual freedom. A listener story about balancing free-pass trips with looming threesome jealousy illustrates how fuzzy rules can test trust. Share your own monogam-ish wins, fails, or questions at coffeeandcleavage.com.

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  17:28
• Dirty Talk Fails & Praise Kink Secrets 😈

  In this episode of Coffee and Cleavage, hosts Lynnie, Shantal, and Gary tackle dirty talk and praise kink—two listener‑requested topics that can take intimacy to the next level. They dissect common missteps (jumping from silence to X‑rated, cliché porn lines, ignoring body language) and offer practical fixes, from slowing down and reading the moment to using “What if…?” questions and seductive pauses. A fan story about an accidental “Yes, mommy” sets the stage for laughs and genuine advice. 

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  14:06
• Creator Confessions, Cringe Moments & What We’d Do With 1 Day Left 😳🔥

  In this episode of Coffee and Cleavage, Lynnie, Shantal, and Gary get personal with a creator-focused Q&A. From the highs and lows of content creation to the moments they’ve been truly embarrassed, the trio opens up about what it’s really like behind the scenes.They reveal whether they tell people what they do for a living, how they keep ideas flowing, and share what they'd do if they only had one day left to live. Plus: Are they girly girls, or down to get dirty (and maybe go camping)? It's a raw, fun, and honest look into their lives as creators.

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  18:38
• Murder Vibes & Dick Pics? The Worst First Dates We've Ever Heard

  In this episode of Coffee and Cleavage, Lynnie, Shantal, and Gary react to one of the craziest dating stories yet—a woman goes on a late-night coffee date, ends up in a dark construction site fearing for her life... and then gets a dick pic the next morning.They also break down the viral “Worst First Date Spots” list—from Cheesecake Factory to coffee shops—and debate whether these locations are truly bad or just misunderstood. Is it about effort, vibes, or just expectations? And what does a date spot say about the kind of connection someone wants?

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