When High School prom king and all round coolest guy in the neighbourhood Zack (Freddie Prinze Jnr.) is told by his girlfriend Taylor (Jodi Lyn O'Keefe) that she's leaving him for Brock Hudson, star of MTV's The Real World, he's naturally more than a little put out. After all it doesn't do for the class president and captain of the school soccer team to be seen with anything less than the prettiest girl in the school, especially with prom night coming up. Being the sort of guy that he is, Zack bets his best friend Dean that he can take any girl and turn her into a potential prom queen. All it takes is the right hair and a bit of make up. Naturally Dean gets to pick the girl. Unhappily for Zack, Dean picks social misfit, angry at everybody, bespectacled, paint splattered Laney Boggs. Laney doesn't have time for trivialities, gossip or guys... least of all Zack.