Josie Geller (Barrymore), copy editor on the Chicago Sun-Times, has led a sheltered life. All that may change, however, when her editor (Marshall) gives her a big writing break by sending her back to school for an exposé on errant youth. Her own teenage years, however, were a nightmare of humiliation, so what's to guarantee that things will improve second time around? Choosing the wrong clothes on the first day isn't an auspicious start, and history begins to repeat itself until her jock brother (Arquette) goes undercover to improve her popularity, and she catches the eye of the English teacher (Vartan). This could be her chance for romance, but how can she tell him she's actually 25 without blowing her story? There's a contradiction at the heart of the film which suggests that nerds are people too, before setting out to transform Barrymore from geekette to hip and groovy young person. Shameless contrivance the lot of it, but Barrymore again displays her remarkable ability to get the audience rooting for her singular blend of vulnerability and sunny optimism.