Some things never change, like the feuding cliques in high school, the cool ones and the geeks. Then there is the constant striving for peer approval and the endless pressures to measure up to someone else's expectations. The universal challenge for every adolescent is to find his or her true self and let it bloom — no matter what!
In this romantic comedy directed by Raja Gosnell, Drew Barrymore plays Josie, a smart but uptight 25-year-old copy editor at the Chicago Sun Times. She almost keels over with delight when the owner of the newspaper (Garry Marshall) orders her to go undercover at a local high school to report on today's teens. Although her boss (John C. Reilly) doubts that she will rise to the occasion, her friend and co-worker Molly (Anita Brandt) thinks she can. Only trouble is that Josie, a self-described "geek to the core," is haunted by the humiliations she suffered when she was really seventeen.
The screenplay by Abby Kohn, Marc Silverstein, and Jenny Bicks humorously depicts all the flubs and follies of Josie's re-entry into high school. Although she finds an ally in Aldys (Leelee Sobieski), a math wiz, and a real fan in Sam Coulson (Michael Varten), a sensitive and supportive English teacher, the hard-pressed reporter must turn to her socially adept brother Bob (David Arquette) for help in negotiating the treacherous waters of becoming popular at the school. The heart-affecting finale of Never Been Kissed turns the sports shrine of the pitcher's mound into a shrine for love.