At Vernon Academy, a prestigious boys' preparatory school in Illinois, Jonathan Ogner (Andrew McCarthy) arrives on campus to begin his senior year. Upon entering his dormitory, he is greeted by his new roommate, Squire Franklin Burroughs IV (Rob Lowe), who is nicknamed "Skip." Following a brief chat, Skip coerces Jonathan to dress in women's underwear as part of senior-class ritual, then locks him out of the building, exposing him to ridicule by the other students. Later, Skip apologizes for the prank, explaining it as a school tradition. Jonathan endures the taunts of his classmates until lunch the next day, when he runs from the cafeteria in tears. Skip returns to his room and discovers Jonathan hanging from the ceiling. The horrified student fetches Mr. Kennedy (Remark Ramsay), the headmaster, but when they enter the room, Jonathan's body has been replaced with a mannequin bearing Kennedy's likeness. The prank earns Jonathan the respect of Skip and his classmates. That night, over a bottle of vodka, Jonathan admits that he cheated on the Scholastic Aptitude Test, or SAT, believing that his "life depends" on being accepted to Harvard University, even though he has always been an exceptional student. He and Skip sneak out of the dormitory to meet Lisa (Virgina Madison) and Susan (Deborah Thalberg), who attend Vernon's sister school, Foxfield Academy. Jonathan ruins the evening by vomiting in the backseat of Skip's car. Sometime later, Skip appoints Jonathan as secretary to the school's dance committee, which travels to Foxfield to meet with Headmistress DeBreul (Fern Persons) and several students, including Lisa and Susan, to plan a Halloween dance. Jonathan's clumsiness in the presence of the women causes a series of mishaps, including the baring of Lisa's breasts and the destruction of a vase given to the school by Eleanor Roosevelt. Jonathan is banned from Foxfield for life, denying him the only source of female companionship within a hundred miles of Vernon. Skip directs Jonathan to the Free and Easy Club in Chicago, Illinois, where he is likely to meet a sex partner. Skip also instructs Jonathan to return to school with a pair of panties as evidence of his conquest. At the club, Jonathan endures two awkward encounters before he meets Ellen (Jacqueline Bissett), an older, uninhibited English woman in her late-thirties. Taking Skip's advice, Jonathan lies about his age, saying he is a doctoral candidate at Northwestern University. Afraid of further embarrassing himself, Jonathan leaves the bar and hails a taxi. Ellen joins him and directs the driver to her hotel, where she and Jonathan make love in an elevator. Two days later, Jonathan returns to Vernon with a pair of Ellen's panties, and word spreads quickly of his sexual prowess. During a subsequent tryst in Chicago, Ellen asks to visit Jonathan at Northwestern the following weekend. When Jonathan claims that he will be attending a conference in New York City, Ellen offers to meet him there, leaving Jonathan no choice but to make travel plans. In a Manhattan clothing store, Ellen inadvertently sees Jonathan's student identification card and (seeing that he is underage and lied to her about himself attending Northwestern) runs from the store. Before Jonathan can stop her, she speeds away in a taxi. Jonathan returns to Vernon in a state of depression, resulting in a decline in his health and his schoolwork. Skip tries to lift his roommate's spirits, but makes no progress until Jonathan is notified that he has been accepted to Harvard. Over the Christmas holidays, Jonathan visits Skip at the Burroughs family's lavish estate. While the boys converse with Mr. Burroughs (Cliff Robertson) in the den, Skip's mother, who happens to be Ellen, appears. Following a brief introduction and an awkward pause, Ellen retires to her bedroom. At dinner, Ellen drinks heavily while Jonathan struggles to hide his discomfort. Afterward, when Mr. Burroughs scolds Ellen for her behavior, she seeks comfort from Jonathan, who declines her advances. Jonathan leaves the next day at Ellen's request. Upon returning to school, the students of Vernon learn that they are under investigation by a man named Balaban (Stuart Margolin), whom they believe to be a drug enforcement agent. After flushing several pounds of marijuana down the school's toilets, it is revealed that Balaban is targeting students who cheated on the SAT. Over the next few weeks, Jonathan receives several desperate phone calls from Ellen, until he finally agrees to meet her in Chicago. Skip asks to join him, but Jonathan insists on going alone, purportedly to mourn his ill-fated romance. In Chicago, Ellen and Jonathan exchange angry words before falling into each other's arms and making love. Meanwhile, Skip arrives in the city with friends from Vernon and Foxfield with the intention of surprising Jonathan, but when they burst into the hotel room, Skip is appalled at the sight of his mother in bed with Jonathan and runs from the room. Back at Vernon, Skip tells Jonathan that he is not upset by the affair, but is unable to hide his anger, and shows little emotion upon learning of his mother's commitment to a mental hospital. Later, in the cafeteria, Kennedy introduces Balaban to the students, and announces that each of them will be interviewed as part of the investigation. Although Jonathan manages to hide his guilt from Balaban, he worries that Skip may betray him as an act of retribution. When Skip is summoned by Balaban, he defies the investigator and utters an obscenity as he leaves the room. The incident makes Skip a hero among the students, and exacerbates Jonathan's guilt. He tries to instigate a conversation with his roommate, but Skip remains silent until Jonathan makes a provocative statement about Ellen, and a brawl ensues. The boys take the fight into the wooded area behind the school, and then into the dormitory. When both are exhausted, Jonathan explains that he was truly in love with Ellen, but promises never to see her again. Skip offers his forgiveness.
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