Season 6: Episode 129: Be Drew to Your School
Drew is embarrassed after several people who knew him from the Future Leaders of America in high school come to school for Career Day and see him working in the cafeteria. He wonders when his life got off-track. He recalls being ignored by Kate and pantsed by jocks on his first day of high school. Kate blames herself for his misfortune. She reveals that during their sophomore year, she answered a question when she wasn't really listening and inadvertently advised Drew to get black glasses instead of contacts. Drew was then seen as a nerd and received regular beatings. Lewis argues that he is at fault because he introduced Drew to beer during their junior year. Oswald confesses to spilling chocolate milk all over Drew's application to MIT, then replacing the essay with moronic babbling. He didn't tell Drew, who sent in the application. Drew insists that he could have made better decisions, but liked getting attention from the attractive school nurse after each crisis. He comes to the realization that he is a "pity-whore."