Holden has recently failed out of school and is dreading facing his parents and himself. He wanders around the city to avoid going home early and alerting his parents that something is wrong. He knows what their reaction will be since he has failed out of several schools already. In addition, wandering around the city helps him to avoid dealing with his own emotions.

Holden is desperately seeking help, although he is unaware consciously of this fact. He is good at avoiding people, but especially good at avoiding himself. Holden has been unable to come to terms with the major tragedy of his life—the death of his brother Allie—and all of his actions are a means of avoiding the truth.

A major concern of Holden’s is Jane Gallagher. He has always thought highly of her and now he recalls spending time with her in the past. He thinks back to playing checkers with her, her family, and how he enjoyed spending time with her. Holden cares for Jane and she is the only one he trusted enough to show the poems on Allie’s baseball mitt to. Holden admits that he was happy when he was with Jane, a positive feeling he has been unable to have lately. He cannot think of Jane with Stradlater because “it drove me crazy” so he goes out.

He wanders around New York City seeking companionship, but failing to find anyone who genuinely cares about him. He strikes up conversations with strangers but does not get the help he needs. For instance, he asks the cab driver, Horwitz, about the ducks in the frozen pond. Holden’s concern is that they have no place to go in the winter; he identifies with those ducks because he feels he has no place to go since he cannot return to school or home. However, Horwitz is more annoyed than understanding: he tells Holden his question about the ducks is stupid. Horwitz turns the conversation to the fish because he knows that the fish stay in the frozen pond; when Holden challenges him, Horwitz becomes impatient. “What’sa matter with ya?” Holden gets no compassion from this conversation and no answer to his original question. He needs to know that the ducks are taken care of when things become difficult, just like he needs to know that he’ll be taken care of now that things are difficult for him.

So far, Holden does not have that feeling of comfort and care that he so desperately craves and needs as he becomes more and more ill. Except for his little sister Phoebe, there is no one in Holden’s life that he genuinely feels close to. Being alone would force him to think about truth, and he doesn’t feel capable of dealing with his brother’s death yet. He’d rather seek out the company of strangers that he believes are all “phonies” and “jerks,” than be alone and afraid.

Holden travels to New York City for a variety of reasons. For one thing, he does not want to have to face his parents, because the reason he's coming home early is that he's been kicked out of school. This is the third time this has happened, and Holden knows his parents will be less than pleased. Holden also wants time to rest up and think about where he's going and how much the adult world terrifies, fascinates, and disgusts him.

In chapters 11 and 12, Holden is mostly aimless during his time in NYC. He thinks about Jane Gallagher, a girl with whom he had a close relationship one summer. He is anxious over whether or not she did anything sexual with Stradlater when she went on a date with him. Then he takes a cab to a nightclub in Greenwich Village, but his conversation with the cab driver about where the ducks go during the winter makes him feel more alone, since the driver responds rudely, and he is frustrated by what he perceives as phoniness in the nightclub patrons.

During all this time, Holden is trying to find someone to connect with, the way he connected with Jane, but no one fits the bill. He feels all the people around him are shallow and "phony," which makes him retreat more into himself. The NYC setting emphasizes his loneliness in a crowd. So, his "rest" trip in the city is less restful than he intended.

Holden Caulfield is Salinger's protagonist in The Catcher in the Rye. When Holden gets word that he is being kicked out of this third prep school, Pencey, he is worried about going home. His home is in New York City, but he doesn't want to go to his parents' apartment. In fact, he doesn't want to see his parents until after they have received the letter from Pencey informing them of Holden failing out of school again. As a result, he decides to go to New York City and stay in a hotel for a few days. This will give him some time to think about his life and what he wants to do with it, but mostly, he's avoiding going home because he doesn't want to face the consequences. Another reason Holden leaves school early is because he doesn't feel like he belongs at Pencey anymore. Right before he exits the dorm building he says the following:

"All of a sudden, I decided what I'd really do, I'd get the hell out of Pencey—right that same night and all. I mean not wait till Wednesday or anything. I just didn't want to hang around any more. It made me too sad and lonesome. So what I decided to do, I decided I'd take a room in a hotel in New York . . . and just take it easy till Wednesday. Then, on Wednesday, I'd go home all rested up and feeling swell" (51).

Holden says this in chapter seven, and he does exactly as he claims. He heads to New York, doesn't go home, and finds a cheap hotel to stay in for a few days. In chapters 11 and 12, then, he is already in New York City. Chapter 11 is mostly about Jane Gallagher, the girl Holden on whom Holden has a crush. He reveals more about his relationship with her and how they used to spend time together during their summers in Maine. They played golf together and checkers together, and they almost made out.

Chapter 12 shows Holden falling deeper into depression and loneliness as he seeks places to hang out and feel accepted until Wednesday when he plans to go home. Holden runs into a couple who know his older brother, he talks with a cab driver about where ducks go in the winter, and he criticizes almost everyone he sees for being phonies.

Holden goes to New York in Chapter 7 after he's thrown out of school. When he leaves school, he is sad, hurt, lonely, feels abandoned by his friends, and feels guilt about hurting his mother.

Chapters 11 and 12 tell about what Holden is doing after he's arrived in New York. He goes to the lounge in his hotel and then takes a taxi to Ernie's. He tries to make friends with the cab driver, asking him to have a drink with him. These chapters continue to reflect Holden's loneliness and depression.

Holden has no strong reason for going to Manhattan. He just doesn't like hanging around his school in Pennsylvania after having been expelled. He feels isolated and unwanted. He begins his story by describing how he was "ostracized" by the fencing team for losing all their equipment on the subway. He has already been "ostracized" by the school administrators. He doesn't want to go home any sooner than he has to, because he knows he is going to get chewed out by his father after flunking out of his third prep school. Young people are usually most flush around Christmas time. Holden is feeling rich. At the end of Chapter 7 he writes:

After I got packed, I sort of counted my dough. I don't remember exactly how much I had, but I was pretty loaded. My grandmother'd just sent me a wad about a week before. I have this grandmother that's quite lavish with her dough. She doesn't have all her marbles anymore--she's old as hell--and she keeps sending me money for my birthday about four times a year.

He will reveal that he has even more riches when he proposes to Sally Hayes:

"I have about a hundred and eighty bucks in the bank. I can take it out when it opens in the morning....No kidding. We'll stay in these cabin camps and stuff like that till the dough runs out, I could get a job somewhere and we could live somewhere with a brook and all and, later on, we could get married or something."

All of Holden's experiences with people during this terminal stage of involvement with Pencey Prep are unpleasant, especially his interview with Mr. Spencer and his fight with his roommate Stradlater. He doesn't feel like sleeping in his own room after fighting with Stradlater, and his neighbor Ackley obviously doesn't like him sleeping in his roommate Ely's bed. Holden may feel as if he is being slowly and subtly pushed out of Pencey. It would be a familiar feeling, since he has already experienced it at two other prep schools. He leaves for New York because he feels he no longer belongs at Pencey. He will find eventually that he doesn't belong in Manhattan either.