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 teenager reputation as a 'geek to the core', Josie is a 25-year-old who has never ever had a serious love relationship - she has never really been kissed. Against all odd, 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.