Jack Singer teaches English at a private school in New York during the 1960s and 1970s. He is often timid or awkward in social settings. He discusses this often with his psychoanalyst, Dr. Morales, whom he sees three times a week. Dr. Morales has a Spanish accent and is often vulgar. He chastises Jack for his refusal to pursue sexual relationships with women. Specifically, Dr. Morales recommends that his patient should sleep with Allegra Marshall, a mother and widow whom Jack met at a work function and found attractive. Soon after, Jack is on his off-period when he notices that Allegra's son is sick and offers to drive him home. When he arrives at the home, Jack makes an awkward advance on Allegra and leaves quickly, feeling embarrassed. Jack blames his psychoanalyst and leaves his next session early when he begins to feel ill. Singer soon begins to experience flu symptoms and stays home sick from work for several days, even after he feels better. Eventually, Allegra Marshall stops by to check in on him and apologize for their awkward interaction. When Jack explains that his analyst suggested that she may be interested in him, Allegra says he was right. The two begin to see each other in secret, and Jack is astonished by Allegra's extreme wealth. While the couple have sex, Jack hears Dr. Morales' voice congratulating him.