The film chronicles nerdy high school senior Danny Stein (Steven Kaplan) and his unsuccessful attempts to secure a prom date while his divorced father and mother (played by William H. Macy and Cheryl Hines respectively) are on their own unsuccessful quests to find love. The film's name comes from the fact that the most unpopular kid in school, Bart Beeber (Chad Jamian Williams), not only secured a date for the prom, but got a hotel room after as well. This is a source of great anxiety for both Danny and his family.