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Holden returns to his dormitory where he finds Robert Ackley, an obnoxious student with a terrible complexion who will not leave Holden alone, and Ward Stradlater, Holden's roommate. Stradlater is conceited and arrogant, a secret slob' who asks Holden to write an English composition for him. Stradlater prepares for a date with Jane Gallagher, a friend of Holden from several summers before, while Holden goes with Ackley and Mal Brossard into New York City to see a movie. When he returns, Holden does write the composition for Stradlater about his brother's baseball mitt. Holden tells about how Allie died of leukemia several years before and how he broke all of the windows in his garage out of anger the night that he died.
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On the train to New York City, Holden sits next to the mother of a Pencey student, Ernest Morrow. Claiming that his name is actually Rudolf Schmidt (the name of the Pencey janitor), Holden lies to Mrs. Morrow about how popular and well-respected her son is at Pencey, when he is actually loathed by the other boys, and even invites her to have a drink with him at the club car. When Holden reaches New York, he does not know whom he should call, considering his younger sister, Phoebe, as well as Jane Gallagher and another friend, Sally Hayes. He finally decides to stay at the Edmond Hotel. From his window he can see other guests at the hotel, including a transvestite and a couple who spit drinks back at each other, which makes him think about sex. He decides to call Faith Cavendish, a former burlesque stripper and reputed prostituted, but she rejects his advances. Instead, he goes down to the Lavender Room, a nightclub in the Hotel, where he dances with Bernice Krebs, a blonde woman from Seattle who is vacationing in New York with several friends. Holden thinks that these tourists seem pathetic because of their excitement over the various sights of the city.
After leaving the Lavender Room, Holden decides to go to Ernie's, a nightclub in Greenwich Village that his brother, D.B., would often frequent before he moved to Hollywood. However, he leaves almost immediately after he arrives, because he sees Lillian Simmons, one of D.B.'s former girlfriends, and wishes to avoid her because she is a phony.' He walks back to the hotel, where Maurice, the elevator man, offers him a prostitute for the night. When this prostitute arrives, Holden becomes too nervous and refuses her. She demands ten dollars, but Holden believes that he only owes five. Sunny (the prostitute) and Maurice soon return, however, and demand an extra five dollars. Holden argues with them, but Maurice threatens him while Sunny steals the money from him. Maurice punches him in the stomach before he goes. Holden then imagines shooting Maurice in the stomach and even jumping out of the window to commit suicide.
Holden calls Sally Hayes to meet her for a matinee and leaves his bags at a locker at Grand Central Station so that he will not have to go back to the hotel where he might face Maurice. At Grand Central he talks with two nuns about Romeo and Juliet and insists on giving them a donation. Before meeting Sally, Holden shops for a record for Phoebe and feels depressed when he hears children singing the song "If a body catch a body coming through the rye." He and Sally go to see a show starring the Lunts, which he knows Sally will enjoy because it seems sophisticated. When Holden sees Sally, he immediately wants to marry her, even though he does not particularly like Sally. After the show, Sally keeps mentioning that she sees a boy from Andover whom she knows, and Holden responds by telling her to go over and give the boy "a big soul kiss." When she talks to the boy, who goes to Andover, Holden becomes disgusted at how phony the conversation is. Holden and Sally go ice skating and then have lunch together. During lunch, Holden complains that he is fed up with everything around him and suggests that they run away together to New England, where they can live in a cabin in the woods. When she dismisses the idea, Holden calls her a "royal pain in the ass," causing her to cry.
After the date, Holden calls Carl Luce, a friend from the Whooton School who goes to Columbia and meets him at the Wicker Bar. Carl soon becomes annoyed at Holden for having a "typical Caulfield conversation" that is preoccupied with sex, and suggests that Holden see a psychiatrist. Holden remains at the Wicker Bar, where he gets drunk, then leaves to wander around Central Park. He nearly breaks down when he breaks Phoebe's record, and thinks he may die of pneumonia. Thinking that he may die soon, Holden returns home to see Phoebe, attempting to avoid his parents. He awakens her, but she soon becomes distressed when she hears that Holden has failed out of Pencey, and tells him that their father will kill him. He tells her that he might go out to a ranch in Colorado, but she dismisses his idea as foolish. When he complains about the phoniness of Pencey, Phoebe asks him if he actually likes anything. He claims that he likes Allie, and he thinks about how he likes the nuns at Grand Central and a boy at the Elkton Hills school who committed suicide. He tells Phoebe that he would like to be "a catcher in the rye," and he imagines himself standing at the edge of a cliff as children play around him. He would catch them before they ran too close to the cliff.
When his parents come home, Holden sneaks out to stay with Mr. Antolini, his former English teacher at Elkton Hills. Mr. Antolini tells Holden that he is headed for a serious fall and that he is the type who may die nobly for a highly unworthy cause. He quotes Wilhelm Stekel: "The mark of an immature man is that he wants to die nobly for a cause, while the mark of the mature man is that he wants to live humbly for one." Holden falls asleep on the couch, and when he awakens he finds Mr. Antolini with his hand on Holden's head. Holden immediately interprets this as a homosexual advance, and decides to leave. He tells Mr. Antolini that he has to get his bags from Grand Central Station and that he will return soon.
Holden spends the night at Grand Central Station, then sends a note to Phoebe at school, telling her to meet him for lunch. He becomes increasingly distraught and delusional, believing that he will die every time he crosses the street and falling unconscious after suffering from diarrhea. When he meets Phoebe, she tells him that she wants to go with him and becomes angry when he refuses. He buys Phoebe a ticket for the carousel at the nearby zoo, and as he watches her, he begins to cry.
Holden ends his story here. He refuses to tell what happened next and how he got sick, and tells how people are concerned about whether or not he will apply himself next year. He ends the story by telling that he misses Stradlater and Ackley and even Maurice.