"Hello, I'm Jerri Blank and I'm a 46-year-old high school freshman. For 32 years I was a teenage runaway. I was a boozer, a user, and a loser. My friends were dealers, cons, and 18 karat pimps. But now I'm out of jail, picking up my life exactly where I left off. I'm back in high school, living at home, and discovering all sorts of things about my body. I'm finding out that though the faces have changed, the hassles are just the same."
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.
Everyone's got careers on the brain during Flatpoint's ""Yes You Can't"" career exploration week -- and not just the students. Mr. Noblet revisits his dreams of rockstardom, Mr. Jellineck quits teaching to pursue his art, and Jerri tries to decide between a career in the flower factory or as a junkie whore.
Jerri suffers a devastating loss and can find no sympathy for her grief, though Mr. Jellineck chips in with his special blend of self-important empathy. The Father-Daughter Sack Race plays a pivotal role in this Very Special Episode.
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.
Someone hits Mr. Jellineck with their car, and the whole school is turned upside-down trying to find the culprit. Meanwhile, Jerri wrestles with her conscience, and Mr. Noblet considers revealing his secret feelings for Geoffrey in an effort to encourage his recovery.
Coach Wolf assigns marriages for her students for a class project. Jerri get paired up with Ronnie Leggett. After Jerri finds problems with her new “marriage,” she learns that it is not as easy as she thought it will be. Will Jerri be able to save her “marriage” and her grade?
Feeling rejected by her classmates and abandoned by her family, Jerri is seduced into joining a religious cult.
After first attempting to stop Jerri from escaping, the leader of the cult realizes how annoying she is and tries to get rid of her, while Principle Blackman, Mr. Noblet and Mr. Jellineck try to rescue her.
Jerri struggles with class issues as the new shoe of the moment ("Flairs") is a wee bit out of her price range. She snags a job at the local shoe store and schemes to procure a pair of the salacious shoes in time for popular rich girl Melissa's party. However, Orlando has a party scheduled for that same evening, and Jerri's snobbery regarding his lower-income-bracket party threatens their friendship.