Josie Gellar (Drew Barrymore) is a tidy, shy copy editor working for a Chicago newspaper. Frustrated, she wants a break as an investigative journalist, but it comes in an unusual form when the eccentric and authoritarian boss of the paper suddenly picks her to go undercover at a local high school, posing as a 17-year old student. The assignment is complicated by the unfortunate memories Josie has of her school years, when her unwashed geekiness earned her the unenviable nickname "Josie Grossie".
This is a feel-good film, but not necessarily in a bad sense: although it is essentially a comedy with romance, there are some poignant moments that must resonate with anybody who has ever passed through secondary school and wasn't bone-headed enough to be impervious to some of the minor cruelties of adolescent peers.
You know this is going to be a film looking at love, or "love", or "lurve", when in the opening scenes Barrymore is in the canteen with colleagues and goes off into a dreamy soliloquy about having never met the right man to be truly taken up in passion and exchange that special kissing moment with him. The theme is touched upon in an English Literature class where Shakespeare is being discussed, and also allows the English teacher (Michael Vartan) to discuss the suggestion that people in disguise are more likely to feel empowered to do things, whether cross-dressed (as in much of Shakespeare) or in the uniform of a football player. As Hollywood has taken to the wholesale adoption of Shakespearean plays in modern garb, one wonders whether this was the intention here. Later the theme of deception and disguise is further developed when Josie's brother Rob (David Arquette) joins the high school, even though he is 23, in an attempt to escape his dead-end job by wangling a ticket into the lower reaches of professional baseball. The ethical dilemma arises, of course, in his relationship with 16-year old girls. Other romantic entanglements include Josie's boss Gus and her friend Anita (Molly Shannon) and her colleague in the listening van and his girlfriend. Another theme that quickly pops up is that of peer acceptance: Josie wants to fit in badly, just as she did when she was a genuine schoolgirl (student), but acceptance of her, and her fellow geeks who take her under their wing, is not easy, especially by those in the student hierarchy who are considered to be "cool". The film weaves in several flashbacks (at times quite painful) of Josie's humiliating real school career, although Barrymore is made up to look so gawky in these that we have no difficulty in following what is then and what is now. In both timeframes, the events are leading to the school prom, an event that first time round ended in disaster for the heroine. (Funnily enough, this was also the setting for the climactic part of the horror film Carrie, which dealt similarly with the issues of adolescence and acceptance).
Drew Barrymore plays this sort of comedic role excellently, and although the film might be considered light fare, it may evoke thoughts about the pecking order in human society as well as some amusing or poignant memories among those of us who left schooldays behind years ago. The only point where the film stumbles rather is at the end, after Josie has been exposed and goes back to being a reporter. I won't give the ending away (don't worry, it's a happy one), but it did seem a tad contrived, as if the scriptwriters had been delivering against the clock. Some parts of the film were a bit light on the gags, and the tone should be perhaps considered "heartwarming" rather than "hilarious". Those who are uncomfortable with the scene where the class is being taught how to fit condoms onto bananas in the sex education lesson, or with the figure of the adult Anita who in some parts of the film seems obsessed with sex, should consider that overall the film (perhaps unusually in this day and age) appears to extol the virtues of "that special person" rather than the purely sexual element.