Josie Geller (Drew Barrymore) wants more out of life. As a bright twenty-five-year-old copy editor at Chicago's revered newspaper, the Chicago Sun-Times, she yearns to be a reporter. Josie is skilled at her profession, but completely clueless in her personal life. She was a brainy nerd in high school, a geek to the core - kids called her "Josie Grossie" - and she has never had a serious relationship with a man.

But things are about to change for Josie - in ways she could never have imagined - when her dream to become a reporter becomes a reality. But her first assignment couldn't be more nightmarish: she must go undercover at a local high school to report on today's teenagers. Now, eight years senior to the oldest pupil in the class, Josie must figure out her story - and a potential new love - while reliving her horrific adolescence and negotiating high school's social and emotional land mines.