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A modern-day version of George Bernard Shaw's Pygmalion, where Zack Siler (Freddie Prinze, Jr.), is a Los Angeles high school hunk who's been dumped by his popular, but mean-spirited, girlfriend Taylor Vaughn (Jodi Lynn O'Keefe) for a famous volleyball player (Matthew Lillard). Frustrated, Zack accepts a bet from his friends that he can turn Laney Boggs (Rachel Leigh Cook), a geeky girl into the school's prom queen. Naturally he falls in love with her which leads to other complications from each other's friends and enemies alike.