Nerdy high school senior Danny (newcomer Steven Kaplan) has spent six hundred bucks on the hotel room, the limo and the tux for his prom. He's only missing one thing--the girl. Hampered by well-intentioned but clueless advice from his newly-divorced parents (William H. Macy, Cheryl Hines) and unsympathetic mocking from his best friends (Brandon Hardesty, Alia Shawkat), Danny battles peer pressure, teen angst and his own raging hormones as he desperately searches for a prom date. "What other evening in your life is as big? Maybe your wedding night, but odds are that's gonna end in divorce anyway," muses Danny's friend Craig as the two pals lounge poolside in the decidedly unhip retirement community town they call home. Danny's luckless quest turns to panic when he learns that even Bart--the school's biggest dweeb--has secured not only a date, but also a hotel room for the night.
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