The Drew Carey Show - Season 2 - Eps 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).
About The Drew Carey Show

Title: The Drew Carey Show
First Air Date: 1995-09-13
Last Air Date: 2004-09-08
Status: Ended
Rating: 6.55/10 (from 159 votes)
Language: EN
Seasons: 10
Total Episodes: 233
Network: ABC
Genres: Comedy
Production Companies: Warner Bros. Television, Mohawk Productions
Synopsis
Drew is an assistant director of personnel in a Cleveland department store and he has been stuck there for ten years. Other than fighting with co-worker Mimi, his hobbies include drinking beer and not being able to get dates. To make a few extra bucks he has a micro-brewery going in his garage with his buddies.
Cast

Drew Carey
Drew Carey

Ryan Stiles
Lewis Kiniski

Diedrich Bader
Oswald Lee Harvey

Cynthia Watros
Kellie Newmark

Kathy Kinney
Mimi Bobeck Carey