The Drew Carey Show - Season 2 Episode 6 The Day the Music Died

Drew, Lewis and Oswald learn that their high school band teacher, Ms. Blankenship, has died. Drew seems to take the news especially hard. He organizes the band to put together one last performance for her, and becomes furious whenever anyone insults Ms. Blankenship. His friends ask for an explanation, and Drew reveals that he lost his virginity to her. He considers the experience to be special. However, he soon learns that the teacher regularly seduced her male pupils. Drew receives another shock when Kate and Oswald confess that they slept together once in high school. Drew feels like a fool because he was unaware of these secrets. Kate tries to cheer him up by proposing a secret of their own. She declares that they should get married if they are both still single by a certain age (which Drew keeps trying to lower).