Never Been Kissed (1999) - Synopsis

Josie Geller (Drew Barrymore) is a talented copy editor at the Chicago Sun-Times who yearns to become a reporter. But when she finally gets her wish, it turns out to be the assignment from hell: Josie, a self-described "geek to the core," must go undercover at a local high school to report on today's teenagers. Now, at age 25, Josie must figure out her story - and a potential new love - while reliving her horrific adolescence.