Cosby (1996)

Season 3: Episode 17

While searching for a rare part for his beloved turntable, Hilton bumps into an old friend from his bachelor days, Fred. When Hilton and Fred start reminiscing about how they double-dated sisters Mattie and Roberta Singleton, Hilton decides to play matchmaker and prompts Fred into learning whatever became of Mattie. Even now, years later, Fred can't help wondering what might have happened if they remained a couple.... and, thanks to Hilton, he may finally get a chance to find out.