Barrymore plays 25-year-old Josie Geller, a one-time high school misfit turned pedantic and lonely copy-editor for the Chicago Sun-Times. Josie desperately wants to be a reporter, and constantly sends story ideas to her boss, Gus (John C. Reilly). One day during a staff meeting, the tyrannical editor-in-chief, Rigfort (Garry Marshall) assigns her to report undercover at a high school. At first, despite her best efforts and the support of her best friend at the paper, Anita (Molly Shannon), Josie reverts back to her geeky, misfit, high school persona, and becomes friends with fellow geek Aldys (Leelee Sobieski). However, after counselling by her brother, Rob (and with the benefit of hindsight of her original high school career), Josie learns how to let go of who she was in highschool.

A subplot involving the attraction between Josie (who has never had a romance) and young English teacher Sam Coulson is complicated by the fact that Sam thinks Josie is 17-years-old and a student, and therefore out of bounds.

The premise of the film is loosely based on the real-life undercover work of Shann Nix, a San Francisco Chronicle reporter who posed as a high school student to uncover the conditions in inner-city schools in San Francisco. Unlike the fictional character, Nix was not unpopular in high school, and never had a romantic connection with a teacher when she went undercover. The movie is a remake of The Major and the Minor.

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