Pop Culture's Most Beloved Virgins

Aubrey Plaza plays Brandy Klark in the '90s-set film The To Do List. Brandy's a recent high school grad who's trying to lose her virginity (amongst other sexual experimentation) before she heads off to college. I won't give anything away, but she must make the classic decision to have her first time be with the hot, aloof dreamboat or the sweet, best guy friend.