Buttle encounters a beautiful college sophomore, Lisa, who shares his passion for Shakespeare. Intrigued by his knowledge of the bard, Lisa decides to sleep with Buttle and the two engage in an afternoon of earth-shattering sex.
Back at Winslow High, Senate learns that Juan Figgis' mother has been convicted on drug charges and is going to jail. Determined to provide for his family, Juan ignores Senate's pleas to finish his education and drops out of school to support them.
Meanwhile, Lipschultz collapses in class and is rushed to the hospital. A student, Kelly O'Toole, comes forward and confesses that she slipped ecstasy into his coffee as a joke. Harper decides to play hardball - he calls the cops, who take Kelly away in handcuffs, and then proceed to search the lockers.
Senate struggles to do the right thing concerning Juan and calls Social Services, who break up the family. Realizing that he did more damage than good, Senate begins a foundation to raise money to keep Figgis in school and get his siblings back together.
Now madly in love with Lisa, Buttle breaks up with Louisa and continues to ditch classes to spend time with his new girlfriend. He is delirious with joy until Lisa gives him the shocking news that she is actually a senior at Winslow High and has had a crush on him for years.
And as the school shuts down for the winter break, Lauren and Senate slowly warm up to each other.
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