Before meeting Sally Hayes, Holden goes to find a record called "Little Shirley Beans" for Phoebe by Estelle Fletcher. As he walks through the city, he hears a poor kid playing with his parents, singing the song "If a body catch a body coming through the rye." Hearing the song makes Holden feel less depressed.
At the theater, Holden buys tickets for I Know My Love, a play starring the Lunts. He knew that Sally would enjoy it, because it's a sophisticated show starring well-known stars. Holden goes to the Mall, where Phoebe usually plays when she is in the park, and sees a couple of kids playing there. He asks if any of them know Phoebe. They tell him that she is probably in the Museum of Natural History. Holden then reminisces about going to the Museum when he was in grade school. He remembers how he would go there often with his class, but while the exhibits would be exactly the same, he would be different each time in mind and body. Holden considers going to the museum to see Phoebe, but instead goes to the Biltmore for his date with Sally.
Holden meets Sally at the Biltmore, and when he sees her he immediately feels like marrying her, even though he doesn't particularly like her. After the play, when Sally keeps mentioning that she thinks she knows people she sees, Holden replies "Why don't you go on over and give him a big soul kiss, if you know him? He'll enjoy it." Finally, Sally does go to talk to the boy she knows, George from Andover. Holden, of course, notes how phony the conversation between Sally and George is.
Holden and Sally go ice skating at Radio City, then to eat. Sally asks Holden if he is coming over to help her trim the Christmas tree. Holden asks her if she ever gets fed up. He tells her that he hates everything: taxicabs, living in New York, phony guys who call the Lunts angels. Sally tells him not to shout. He tells her that she is the only reason that he is in New York right now. If not for her, he would be in the woods, he claims. He complains about the cliques at boarding schools, and tells her that he's in lousy shape. He suggests that they borrow a car from a friend in Greenwich Village and drive up to New England where they can stay in a cabin camp until their money runs out. They could get married and live in the woods.
Sally tells him that the idea is foolish, for they are both practically children who would starve to death. She tells him that they will have a lot of time to do those things after college and marriage, but he claims that there wouldn't be "oodles" of places to go, and it would be entirely different from how she portrays it. He calls her a "royal pain in the ass," and Sally starts to cry. Holden feels somewhat guilty, and realizes that he doesn't even know where he got the idea about going to New England.
Holden once again considers giving Jane a call to invite her to go dancing. He remembers how she danced with Al Pike from Choate. Although Holden thought that he was "all muscles and no brains," Jane claimed that he had an inferiority complex and felt sorry for him. Holden thinks that girls divide guys into two types, no matter what their personality: a girl will justify bad behavior as part of an inferiority complex for those she likes, while claim those that she doesn't like are conceited.
Holden calls Carl Luce, a friend from the Whooton School who goes to Columbia, and plans to meet him that night. He then goes to the movies and is annoyed when a woman beside him becomes too emotional. The movie is a war film, which makes Holden think about D.B.'s experience in the war. D.B. hated the army, but had Holden read A Farewell to Arms, which in Holden's view celebrates soldiers. Holden thinks that if there is a war, he is glad that the atomic bomb has been invented, for he would volunteer to sit right on top of it.
Holden meets Carl Luce at the Wicker Bar. Carl Luce used to gossip about people who were "flits" (homosexuals) and would tell which actors were actually gay. Holden claims that Carl was a bit "flitty" himself. When Carl arrives, he asks Holden when he is going to grow up, and is not amused by Holden's jokes. Carl is annoyed that he is having a "typical Caulfield conversation" about sex. Carl admits that he is seeing an older woman in the Village who is a sculptress from China. Holden asks questions that are too personal about Carl's sex life with his girlfriend until Carl insists that he drop the subject. Carl reminds him that the last time he saw Holden he told him to go see his father, a psychiatrist.
Holden remains in the Wicker Bar getting drunk. He continues to pretend that he has been shot. Finally, he calls Sally, but her grandmother answers and asks why he is calling so late. Finally, Sally gets on the phone and realizes that Holden is drunk and quickly hangs up.
In the restroom of the Wicker Bar, Holden talks to the "flitty-looking" guy, asking if he will see the "Valencia babe" who performs there, but he tells Holden to go home. Holden finally leaves. As he walks home, Holden drops Phoebe's record and nearly starts to cry when it shatters into pieces. Forlorn, he goes to Central Park and sits down on a bench, fantasizing that he will get pneumonia and have a funeral that people have to attend. He is reassured that his parents won't let Phoebe come to his funeral because he is too young. He thinks about what Phoebe would feel if he got pneumonia and died, and figures that he should sneak home and see her, in case he does die without having a chance to say goodbye.
In Chapter 16, although Holden can himself be a snob, he detests social pretension as manifested by the Lunts (Alfred Lunt and Joan Fontanne, considered the prominent couple in Broadway theater) and Laurence Olivier. Like so many other things, he dislikes both film and theater because they are inherently phony and, in the case of Broadway theater, validate others' notions of their own sophistication. However, Holden does not comprehend the inherent contradictions in his belief system. He rejects superficial markers of status and taste such as Broadway theater, yet in the previous chapter he used superficial markers of status (expensive suitcases) as a mark of validation.
Holden's primary interest shifts from Jane Gallagher to his sister, Phoebe. He even seems more preoccupied in seeing Phoebe than in his imminent date with Sally Hayes, for whom he has little more than contempt. The fascination that Holden has for Phoebe seems part of a longing for childhood. Holden resists change; he dislikes trips to the museum precisely because their static nature reminds him how much he changes at every visit. Holden seems to fear change and maturity, giving great sentimental weight to childish pleasures while fearing the qualities that mark adult life.
In Chapter 17, Holden's date with Sally Hayes reiterates several of the basic problems from which Holden suffers. He has intensely contradictory feelings for Sally, which even he realizes. Although he dislikes her, when he first sees her he feels that like marrying her. Holden shifts from seeming to loathe Sally to seeming to care about her, as when he proposes that they run off to New England and then calls her a pain in the ass once she refuses his offer. The confrontation between Holden and Sally in the restaurant demonstrates Holden's unreliability as a narrator. He does not realize that he is shouting at Sally Hayes through their conversation and denies it repeatedly to both the reader and to himself.
Holden's proposal is a mark of desperation, for he wishes to reject the entire society around him. He does this partially because he cannot coherently articulate what he so dislikes about the society in which he lives. Holden claims that he hates "everything," and locates this aversion in random things such as taxicabs and phonies who call the Lunts "angels." Holden even admits to himself that his actions have no logic, revealing that he does not know where he thought of escaping to New England. This continues a pattern of demonstrated behavior by Holden, while foreshadowing further desperately random actions. The New England idea also reinforces the idea that Holden stands at a difficult boundary between childhood and adulthood. Sally Hayes claims that they cannot run off together because they are still practically children, yet her rejection shows more sensible maturity than Holden's immature notions of running away from home and responsibility.
At this point, then, Holden seems trapped between his fantasy of escape and the realization that he has nowhere to go. In terms of character, he is less an anti-hero, then, then a question mark - completely trapped between motivations, unsure how to cope with the swelling pain. Thematically, Holden seems to be a singular reservoir of unexpressed pain, that has festered and turned into an anti-social soreness towards the world. But it would be a terrible mistake to take Holden as a 'rebel,' or someone who sees value in challenging society. All his rebellious thoughts and instincts are simply the products of fear, anxiety, and shame.
Holden returns to reminiscing about Jane Gallagher in Chapter 18, once again revealing his unfortunately short attention span. Soon after proposing that he and Sally Hayes run off together, Holden has already forgotten Sally and moved on to other considerations. It appears that Holden is always looking for comfort - some sort of fleeting pleasure to take away the pain which threatens to overwhelm him.
In this chapter Salinger allows Holden more coherence than usual. His cynical observations are not always misinterpretations; in some cases, he makes accurate statements about human foibles and failings. His diatribe concerning "inferiority complexes" is a particular case when Holden's suspicions have a particular coherence. He accurately finds that people have hypocritical standards of judgment for others and justify the behavior in those they like while condemning similar behavior in others. That Holden can make such observations is significant for the story, for it reinforces the idea that, although he is perpetually cynical, Holden still has the capability for intelligent and rational thought. This is a significant point, for it implies that external factors have promoted Holden's psychological difficulties and that he is not the perpetual failure that he perceives himself to be. Also, those moments when Holden shows himself to be rational make his outrageous statements more potent, such as when Holden ends his remembrance of D.B.'s war experience with the statement that he would want to sit on an atomic bomb during wartime.
Holden returns to his obsession on sex in this Chapter 19, a preoccupation that demonstrates great immaturity and a lack of propriety toward others. Holden appreciates sexuality in its most lurid forms, relishing Carl's gossip about which actors are closeted homosexuals, and can only conceive of Carl's relationship with the sculptress in terms of exotic sensuality. He even persists after Carl tells him how inappropriate his questions are, barely realizing that Carl is disgusted by Holden's behavior.
Salinger uses Holden's meeting with Carl Luce to give a more broad perspective on his behavior. Once again, this reinforces that others consider Holden to have some significant problems, but Salinger takes this viewpoint further in this chapter. Carl indicates that Holden's behavior when they meet at the Wicker Bar is typical behavior, and not the product of his altered psychological state. Holden has been suffering from his current problems since he went to Whooten with Carl Luce, and these problems have been significant; Carl even had suggested psychiatric treatment for Holden, a relatively significant recommendation in an era when therapy was highly stigmatized. Furthermore, this diagnosis comes from one of Holden's peers. This perspective on Holden's problems cannot be dismissed as easily as others, for Carl's recommendation is not the advice of the elderly Mr. Spencer or another authority figure who presumably could not understand Holden's problems.
Throughout Chapter 20, Salinger continues to foreshadow an eventual suicide attempt by Holden. Holden once again pretends that he was shot, as he did after his confrontation with Maurice, but his thoughts shift to more serious mortal concerns. He imagines his funeral as if it is an impending event, yet is curiously ambivalent about the consequences. His only concern is not whether or not he will die, but how Phoebe will react to his death. Holden's decision to visit Phoebe at the end of the chapter shows that his actions are somewhat premeditated. He approaches this visit as a means to set his affairs in order, as if he knows that he will soon die.
This fantasy, then, is reminiscent of Tom Sawyer's interruption of his own funeral - but in this case, Holden actually finds the possibility of validation and redemption in his own death. In seeming himself dead, it seems, Holden believes that he might find some instinctive motivation for continuing to live. By embracing death, maybe some glimmer of hope and conviction will stir him back to life. It never quite does, however, forcing him to invent bigger and bigger fantasies of death and people mourning him.
Otherwise, Holden continues to display more of his typical inappropriate behavior, as when he calls Sally while drunk and tries to chat with the "flitty-looking" guy. Salinger shows how Holden has become more sensitive to occurrences in this chapter. He nearly breaks down into hysterics when he breaks Phoebe's record, and it is this event that provokes his meditations on death. This foreshadows later instances in which minor events will provoke more serious catastrophes for Holden.