Josie Gellar (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 reputation as a geek to the core, Josie is a twenty-five-year old who has never had a serious relationship - she has never really been kissed!

Against all odds, Josie lands her first assignment as a reporter: she must go undercocver 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 adolesence.