Josie Geller (Drew Barrymore) is a highly intelligent, if pedantic and lonely, copy-editor who desperately wants to be a reporter. She is disillusioned with her life and avoids other people. She is overjoyed to be assigned her to report undercover at a high school to help parents become more aware of their children’s lives.
Her brother reminds her of her own awful high school career, where she was a misfit treated with contempt and cruelty by her peers, and was known as ‘Josie Grossie’. A nickname which continues to haunt her, along with her misery at being treated so brutally. Josie has never had a romance due to her insecurities. She is unnerved, but is determined to carry on with her assignment.
Her first day is miserable; she reverts back to the old geeky persona that ruined her first high school career. She also has horrible flashbacks about an embarrassing moment when she was at high school.
Eventually she writes the story of her own high school career, admitting that she has never been kissed.
Kimberly Greene was the makeup department head; Joni Powell & Lyssa Wittlin Baumert were the makeup artists.