Nicole (MELISSA JOAN HART) and Chase (ADRIAN GRENIER) have been neighbors since they were kids when they were also best friends. Around the time middle school came around, however, the two went their separate ways and now that they're high school students, their two worlds barely intersect.
It turns out that Chase has become something of a beatnik, and enjoys hanging out with his other anti- establishment friends, Designated Dave (MARK WEBBER), so named for his willingness to chauffeur the drunk, and Ray (KRIS PARK) who has a penchant for videotaping nearly everything.
On the other hand, Nicole is part of the "in" crowd, and while hanging out with friends, Alicia (SUSAN MAY PRATT) and Dee Vine (KERI LYNN PRATT), longs for Brad (GABRIEL CARPENTER), the school's blond basketball star.
When Chase's activist girlfriend, Dulcie (ALI LARTER), dumps him, however, and Nicole learns that Brad has asked a cheerleader to their school's centennial dance, she proposes a scheme that may help both of them. By posing as a couple, she figures that they can make the respective objects of their affection jealous, and thus eventually get together with them.
As they begin their ruse where Chase "cleans up" to become part of the popular crowd, their respective friends are shocked not only at their changes, but also to the apparent fact that the two are dating, a point that hits close to home when both Nicole and Chase begin to develop feelings for each other.