The Drew Carey Show

S02E06 The Day the Music Died

Drew, Lewis, and Oswald are devastated to hear about the passing of their beloved band instructor, Ms. Blankenship. Drew takes the news particularly hard and rallies the band to perform a tribute for her, growing angry at anyone who disrespects her memory. When his friends probe for the reason behind his strong emotions, Drew reveals that he lost his virginity to her, cherishing the moment. He is later shocked to discover her pattern of seducing students. The surprises continue when Kate and Oswald admit they had a fling in high school, leaving Drew feeling naive. To lift his spirits, Kate suggests a whimsical pact: if they remain single by a certain age, they should marry, a notion that Drew keeps trying to make happen sooner.