Coffee and Cleavage

In this episode of Coffee and Cleavage, hosts Lynnie, Shantal, and Gary explore two listener dilemmas. One caller’s sister exaggerates his size, leading to mid-hookup humiliation; the hosts discuss rebuilding self-esteem, addressing family sabotage, and whether physical dimensions or chemistry matter most. Another listener loves his relationship but feels unwanted because his partner never initiates sex; the trio outlines respectful strategies to spark her confidence and desire. Additional fan questions tackle whether bad sex justifies ending a relationship, how early is too early to discuss kinks on dating apps, and best hand etiquette during oral. Submit questions at coffeeandcleavage.com.

In this episode of Coffee and Cleavage, hosts Lynnie, Shantal, and Gary answer listener-submitted questions for a behind-the-mic look at their lives. Topics include the only three apps they’d keep if they had to purge their phones, the single skill each host is quietly working on this year, and which past episode challenged them most. They open up about favorite comfort rituals, advice that proved life-changing, the oddest direct messages in their inboxes, and the Hollywood actors they’d cast to play themselves. Rounding out the conversation are thoughts on misconceptions about content creators, the unexpected quality that makes someone unforgettable, personal goals they hope to lock in next year, and a three-item bucket list still waiting to be checked off.  Submit more questions at coffeeandcleavage.com.

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.”

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.

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.