Bart Got a Room (2008)

Danny Stein is a high-school senior and class vice president; he's in charge of the prom, along with Camille, his best friend for years. Everyone including Camille and her parents assumes that Danny will ask her to the prom, but he wants something less platonic and more romantic - more memorable. His choices include the sophomore cheerleader he drives to school, a friend of a friend, and a quiet Chinese girl in his classes. With his parents' help (they're going through a divorce), he gets the tickets, rents a tux, reserves a limo, and, over his mother's objections, gets a room at the prom-site hotel. This, everyone believes, is the way to establish memories. Will anything work out?