Josie Geller (Drew Barrymore) is ready for a change. As the youngest copy editor at a big-city newspaper, she longs to be taken seriously as a journalist. But while Josie excels as the nerdy brain at work, her personal life is another story. Still plagued by her teenage reputation as a 'geek to the core', Josie is a twenty-five-year-old who has never had a serious love relationship - she has never really been kissed. Against all odds, Josie lands her first assignment as a reporter: she must go undercover posing as a student at a local high school. the situation proves hilarious as Josie attempts to juggle her story assignment, a potential new love and the never-ending dramas of adolescence.