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 schoo

Coach Riley has a serious crush on Marylin Sudor but is nervous about asking her out due to their racial differences. But when he and Buttle ask Ms. Sudor how she and Ms. Hendricks feel about dating white men, Marylin mistakenly assumes Coach wants to ask Marla out. Riley's ""infatuation"" with Marla appears on Sheryl Holt's Web site and Ms. Hendricks becomes extremely excited about the prospect of dating Coach.

Eventually, Kevin tells Marylin the truth and she is forced to break the news to Marla, who is deeply hurt. While Kevin and Marylin do make plans to eventually go out, they decide to wait until Marla has gotten over her disappointment.

Meanwhile, Harper is concerned about the cheerleading squad. They have been rehearsing for an important competition, but their new routine is extremely sexual. The choreographer argues that it's impossible to tone down the program, so Harper cancels the meet.

Regardless of the consequences, Lisa and Buttle continue to tempt fate and continue their