After several failed attempts to find Jonathan a date, Skip decides that it is his sworn duty to help his friend have a successful sexual encounter. Skip decides to send Jonathan to Chicago to meet a girl and gain sexual experience before both of their reputations are ruined. Jonathan is picked up by Ellen, a beautiful older woman, and has an affair with her. Jonathan begins to fall in love with Ellen even though the older woman knows it to be just a fling between them. Jonathan lies and claims to be a Ph.D. student. When Jonathan proclaims his love to Ellen during one of their sessions, Ellen begins to have second thoughts about continuing the relationship. Her decision is finalized when she discovers that Jonathan is not only much younger than he had originally claimed to be, but he also attends the same school that her own son attends.