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.

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.

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.

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.

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.

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.