Joel Goodson is a high-achieving high school student who lives with his wealthy parents in the Chicago North Shore area of Glencoe. His father wants him to attend Princeton University, his "alma mater", so Joel participates in Future Enterprisers, an extracurricular activity in which students work in teams to create small businesses. When his parents go away on a trip, Joel's friend, Miles, convinces him to take advantage of his newfound freedom to have some fun. On the first night, he raids the liquor cabinet, plays the stereo loudly, and dances around the living room in his briefs and button-down shirt to "Old Time Rock and Roll". The following day, Miles calls a prostitute named Jackie on Joel's behalf. When Jackie turns out to be a transvestite, Joel pays her just to leave, but before she does, she gives Joel the number for another prostitute named Lana. That night, Joel is unable to sleep and hesitantly calls Lana, who turns out to be a gorgeous blonde woman, and they stay sexually engaged all night.