Jerri's back out of prison and back to being a freshman at Flatpoint High. . . again. She's determined to be a proper girl, if only that little devil on her shoulder would stop trying to convince her otherwise. Coach Wolf encourages her female students to remain chaste and convinces Jerri that she can reclaim her virginity. All the girls take to wearing ""Never Been Touched"" ribbons with a cherry dangling from them.

Jerri falls for Alan, a blind boy at her school with football aspirations. The rest of the team, however, is skeptical about his abilities, but with Jerri's encouragement, Alan rises to the occasion.

Jerri has a difficult time in Noblet's class when she's asked to read from Moby Dick. When she realizes that cheerleaders get all the guys, plus they're treated with kid gloves in class, she decides to try out for the Donkettes squad. She learns right away that cheerleaders need to know how to spell. Her illiteracy is quickly revealed and Jerri is immediately subjected to complete humiliation.

Told in her art class to photograph something that represents freedom, Jerri creates a nude self-portrait which is immediately banned by the principal. So Jerri goes on a hunger strike.

When Jerri discovers her American Indian heritage, she attends a camp run by a councilor who teaches adopted Indian children about aspects of their culture, such as alcoholism and gambling.

Jerri joins the track team, but years of hard living have taken their toll on her physique. She turns to supplements of a most dubious nature to improve her performance, and the results surprise everyone at Flatpoint.

At the bequest of Mr. Noblet, Jerri takes over an advice column formerly penned by Mr. Jellineck, which results in diabolical intentions on Geoffrey's part towards Chuck, and anger from nearly everyone in Flatpoint High towards Jerri.

Winona Ryder stars as Fran, the coolest girl in school, who makes a bet that she can make Jerri so cool that even Brent Brooks (Paul Rudd) will ask her out.