He takes a taxi to the station and gets on the train to the city. Here he meets a woman, who turns out to be a mother of one student from Pencey, which Holden happens to know. He makes up some stories about the woman’s son just to impress her. Afterwards he regrets it. When he gets to New York he goes to a hotel to spend the night there. He realizes he doesn’t want to sleep yet so he decides to head for down town to the club. Here he meets some young ladies, who according to his opinion “are not quite as good looking”. However; he invites one of them to join him for a drink. But as soon as she starts talking he dislikes her and decides to leave the club. Although he is under age he goes to another club where he asks for some (alcohol) drink. He meets one of his brother’s ex-girlfriends, but doesn’t feel like talking to her since his brother lives in Hollywood now and Holden doesn’t want to explain her everything. He takes a taxi to go back to the hotel. The elevator man offers him a prostitute for 5 dollars. He accepts the offer and goes to his room to get ready for the “lady”. When she comes he is very nervous. He reveals he is still a virgin although all the time until that moment he has been talking about the girls as if he’d had some experiences with them. He doesn’t really want to have sex with the prostitute. He just needs someone to talk to. But the girl doesn’t understand him, so she leaves after taking the money. The next morning, when he wakes up, he is really depressed and thinks about committing a suicide. After a while of thinking he calls his ex-girlfriend and makes a date with her. He still has a lot of time to spend until the date, so he decides to spend it by just wandering in the streets. He takes his suitcase and puts it to “one of those boxes” on the station. He decides to have breakfast at the station. Here he meets two nuns and has a really nice conversation with them. Afterwards he goes to buy a ticket for the play he is to see with Sally. Then he buys a record for his little sister.
On the date with Sally, after the play, when they are sitting in a restaurant and eating, he suddenly feels he’d like to spend the rest of his life with her. He doesn’t even like her that much, he just feels like it at the moment, so he asks her to leave the city with him and go west. Once again he isn’t understood. Sally gets upset and leaves him sitting there alone. Late Holden calls his friend and meets him in a bar. His friend is in a hurry so after a while of talking Holden finds himself once again alone.