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.

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.

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.

Jerri's new daddy Stew starts to act very strangely, which makes Jerri reluctant to bring him to class for Occupation Week.

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.

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.

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.

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.

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 tries to fit in by mixing up a batch of the drug concoction Glint for Poppy, the most popular girl in school... with mixed results.

In order to teach students the responsibility of taking care of a baby, Coach Wolf gives each student a baby.

Jerri's starring role in the school play stirs up a dangerous cocktail of jealousy and regret in her stepmother, Sara

Jerri falls for a transfer student and later discovers the terrible secret that will keep them apart forever.

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 is told she must help Principal Blackman out by turning snitch and rooting out the school retard if she wants to go on the class trip to Good Time Island.

Flatpoint High is up in arms to find out whodunit after someone scrawls a racial slur on the wall.

Jerri finds her calling on the debate team, but can she make it through the dangerous physical training for the big competition?

Noblet discovers that Jerri is a violin prodigy and ruthlessly grooms her to become the star he always wanted to be.

Desperate to become homecoming queen, Jerri concocts some unique strategies to eliminate the competition.

Jerri reverts back to her old ways and succumbs to drugs in an attempt to win the affection of a beautiful female stoner

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.