Feeling like a coward for leaving Ernie’s, Holden walks the forty-one blocks from the nightclub back to the hotel. Along the way, he thinks about his gloves, which were stolen at Pencey. He imagines an elaborate confrontation with the unknown thief, but he acknowledges that he is a coward at heart, afraid of violence and confrontation. When he reaches the Edmont, he takes the elevator up to his room. The elevator operator offers to send him a prostitute for five dollars, and Holden, depressed and flustered, accepts. While waiting in his room, he again thinks about his cowardice, because he feels that his lack of aggression has prevented him from ever sleeping with a woman. Women, Holden believes, want a man who asserts power and control. As he broods, the prostitute, Sunny, arrives. She is a cynical young girl with a high voice. Holden becomes flustered, especially so when she removes her dress. She sits on his lap and tries to seduce him, but he is extremely nervous and tells her he is unable to have sex because he is recovering from an operation on his “clavichord.” He finally pays her the five dollars he owes and asks her to leave. She claims that the price is ten, but he refuses to pay her more, and she leaves in a huff.
Holden sits in his hotel room and smokes for a while. He remembers an incident shortly before Allie’s death when he excluded Allie from a BB-gun game—he still feels guilty for having left Allie out. Eventually, he goes to bed. He feels like praying, but his distaste for organized religion prevents him from following through on his inclination. Suddenly, there is a knock at his door. In his pajamas, Holden opens the door to face the burly elevator operator, Maurice, who has returned with Sunny to collect the extra five dollars Sunny demanded. Holden tries to refuse, but Maurice pins him against a wall while Sunny takes the money from his wallet. Maurice snaps his finger into Holden’s groin, and Holden starts to insult him in response. Maurice slugs Holden in the stomach and leaves him crumpled on the floor. Holden imagines himself as a movie character, taking his revenge on Maurice after having been plugged in the gut with a gangster’s bullet. Finally, he manages to get into bed and go to sleep.
The next morning, Holden calls Sally Hayes and makes a date with her for later that afternoon. He checks out of the hotel and leaves his bags in a locker at Grand Central Station. He worries about losing his money and mentions that his father frequently gets angry when Holden loses things. He also describes his mother a bit, noting that she “hasn’t felt too healthy since my brother Allie died.” Holden worries that the news of his expulsion will particularly distress his fragile mother, for whom he seems to care a great deal.
Holden goes to eat breakfast at a little sandwich bar, where he meets two nuns who are moving to Manhattan to teach in a school. Holden thinks about the superficial money-driven world of the prep school he has just left. Then he talks to one of the nuns about Romeo and Juliet. Despite his earlier expression of distaste for organized religion, he forces them to take ten dollars as a charitable contribution. After they leave, although he realizes he needs money to pay for his date with Sally, he begins to regret having given only ten dollars. He concludes that money always makes people depressed.
During his previous expeditions around town, Holden maintained a distance from the people he was with, dismissing them with scorn. As a result, he was able to protect his vision of an ideal world: instead of dealing with real people and situations, he daydreams about Phoebe’s innocence and Jane’s warmth. Up to this point, Holden has been able to avoid a clash between his real and his ideal worlds, but in these chapters, the conflict becomes unavoidable, and Holden is caught in a moment of crisis and danger.
Sunny represents another of Holden’s attempts at female companionship, but she could not be more different from the idealized Jane for whom Holden yearns. Whereas Holden’s relationship with Jane brought him emotional satisfaction, his relationship with a prostitute can only be superficial, sexual, and devoid of emotion. But Jane appears only in Holden’s memory, while the prostitute appears in his room. She concretizes Holden’s continual conflict, representing something he both wants and doesn’t want, something he needs yet fears.