Played by: Freddie Prinze, Jr. and Rachael Leigh Cook
Zack and Laney were brought together by a bet (sidebar: why do so many people gamble with their hearts in teen movies?), challenging him to transform her from a nerdy artist into the prom queen. But we were betting on this couple way before Laney ditched the glasses for a slinky red dress. As Laney showed Zack to look beyond his clique, he helped her become more confident.