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Elizabeth Halsey (Cameron Diaz) is a poor Chicago area teacher who curses at her students, drinks heavily, and takes copious amounts of drugs. She plans to marry her wealthy fiance, but when he dumps her, she tries to win over substitute teacher Scott Delacorte (Justin Timberlake), who is also wealthy. Their colleague Amy Squirrell (Lucy Punch) is also pursuing Scott, while the school's gym teacher Russell Gettis (Jason Segel) is making advances on Elizabeth.