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Jerri Blank is a 47 year old ex-con, who returns to her childhood home after 32 years of working the streets and in prison. Once she arrives, she discovers her mother is dead and her father is in a self-induced coma. Jerri decides to pick up right where she left off as a freshman in high school, hoping to wake her father with her winning science fair project. Based on the Comedy Central series.
Winona Ryder stars as Fran, the coolest girl in school, who makes a bet that she can make Jerri so cool that even hunky Brent Brooks will ask her out. But members of the school board are plotting to have the school closed.
Both Jerri and Mr. Jellineck must gain the courage to stand up to bullies at the school.
Jerri is getting admirers, but some sexual harassment from Skeet keeps driving them away. When Jerri gets sick of Skeet and his friends harassment, she decides to go to Principal Blackman for help.
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 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.
Jerri's new daddy Stew starts to act very strangely, which makes Jerri reluctant to bring him to class for Occupation Week.
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 discovers something unsettling about her ethnic heritage.
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.
After deflowering a male classmate, Jerri finds out that she has contracted a series of STDs (syphilis 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.
