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.”