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A romantic comedy about a nerdy copy editor who longs to become a reporter at the Chicago Sun Times. Her big opportunity comes in the form of her first undercover assignment, which consists of a feature on what cool high school students are doing. In order to uncover the lives of these hip teenagers, she must return to the high school where she was once considered a nerd and attempt to infiltrate the popular circle. Drew Barrymore stars as the main character of Josie while David Arquette is her brother Rob. Michael Vartan also stars as Josie's love interest.