It's Janey Briggs (CHYLER LEIGH) birthday, but she's not particularly happy. A social outcast at John Hughes High School, the teen lives with her alcoholic father (RANDY QUAID) and younger teenage brother, Mitch (CODY McMAINS), who - like his geeky friends Bruce (SAMM LEVINE) and Ox (SAM HUNTINGTON) - is preoccupied with losing his virginity and is smitten with Amanda Becker (LACEY CHABERT), the "The Perfect Girl."
Unbeknownst to Janey, the popular jock, Jake Wyler (CHRIS EVANS), has made a bet with his friends -- Austin (ERIC CHRISTIAN OLSEN), the other quarterback; Reggie Ray (RON LESTER), the obese and dimwitted lineman; and Malik (DEON RICHMOND) "The Token Black Guy" - that he can turn her into the prom queen before school is out.
As Jake feigns romantic interest in Janey to win the bet - much to the chagrin of her obsessed best friend Ricky (ERIC JUNGMANN) -- and tries to ward off the libidinous advances of his incestuous sister, Catherine (MIA KIRSHNER), other students deal with their particular high school issues.
There's Priscilla (JAIME PRESSLY), the catty head cheerleader whose 1950s style squad-mate, Sandy Sue (JOANNA GARCIA), suffers from Tourette's syndrome. Meanwhile, Areola (CERINA VINCENT) is the foreign exchange student who's always nude, Les (RILEY SMITH) is the weird outsider who sees the beauty of everything, and finally Sadie (BEVERLY POLCYN) is an old reporter working undercover as a high school student.