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Never Been Kissed is a 1999 comedy directed by Raja Gosnell and starring Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, Leelee Sobieski, John C. Reilly, Jessica Alba, Marley Shelton, James Franco, Giuseppe Andrews, Jeremy Jordan and Garry Marshall. Never Been Kissed was produced by Drew Barrymore's production company, Flower Films.

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 to help parents become more aware of their children's lives, having been inspired by the discovery that he was unaware of his son's allergies. 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 high school.

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.

Josie becomes popular and hangs out with the cool crowd while secretly wearing a hidden camera and reporting back information to Gus. In school, the most popular guy likes her and Josie becomes more and more in tune with the generation of high school students that came after her.

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 did not describe herself as unpopular in high school, and never had a romantic connection with a teacher when she went undercover. 
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