Sex, Losers, & Videotape (S05E19)

After Will's breakup with Barry, he teams up with Karen and his boss, Mr. Stein (Gene Wilder), to establish an anti-romance club. They meet twice, bonding over their shared belief that “love stinks.” However, things take a turn when Karen and Mr. Stein begin a secret relationship, enjoying intimate moments without Will's knowledge to spare his feelings. Upon discovering their romance, Will disbands the club, insisting, “If you’re going to have a club for lonely and bitter people, at least stay bitter.” Meanwhile, Grace attempts to create a sultry video for Leo, who’s away in Africa. Jack overhears her singing and criticizes it, suggesting she join his acting class for more openness. After attending a session that proves unhelpful, Jack secretly films Grace in the shower. When she discovers the footage, she acknowledges its sexiness, only to realize Jack has shared it with his classmates.