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'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 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.
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.
After deflowering a male classmate, Jerri finds out that she has contracted a series of STDs (syphillis infested with crabs which are carrying gonorrhea) and must inform all her partners of her discovery. Meanwhile, Mr. Jellineck and Mr. Noblet have problems concealing their own bout with a particularly noticeable STD.
Jerri and class hunk Laird are having a fling, but he is insistent on keeping it a secret. So Jerri finds herself forced to hide out in odd places like Laird's locker, the trunk of his car, a trash can, etc., so they can continue their secret rendezvous. Meanwhile, Jerri's stepmother experiences relationship troubles with Stew, prompting an unusual bonding moment between stepmother and stepdaughter.
Jerri is asked out at a school wrestling game, but the boy later takes back his offer because other boys are saying mean sexual things to Jerri and she does nothing about it. So Tamela tells her she was a victim of sexual harassment and she needs to stick up for herself. Jerri later starts liking another guy, but is afraid it will end soon because of the other guys harassing her.
A new student comes to Flatpoint High, who turns out to be a bully who everyone is afraid of. When Jerri stops a fight with the bully and her friend Tammy, the bully schedules a fight for after school. Everyone keeps telling Jerri that she shouldn't fight and find peace, but Jerri feels she should live by the street code and fight. Geoffry gets a bully of his own when a homosexual hater substitute confronts him.