When Stradlater got back, Holden was very worried that he had taken advantage of poor, innocent Jane. Holden's insecurity pushed him so far that he attacked Stradlater, knowing it was a battle he would lose. After the fight, Holden decided he is going to leave Pencey early and stay in a cheap, New York hotel until Wednesday, when he is supposed to be home. He does this to get away from his problems at Pencey but he does not realize that he will encounter bigger problems outside Pencey.
In New York, Holden's depression keeps growing every second. When he reaches the hotel, he gets a very crummy room, which depresses him. The bellhop also depresses him since he is old and has a comb over. He then goes down to the Lavender Room, a club in the hotel. He tries to order alcohol but gets shot down by the waiter. Later on, he goes to another bar called Ernie's and orders a Scotch and soda. While he is at the bar, an old friend of his brother's, D.B., comes over to talk to him. She invites him to sit with her and her date but he lies and tells her that he has to go meet somebody. This shows two things that are bringing him down; he keeps lying to everyone and he does not sit with her because he finds her phony. The problem is that Holden finds almost everybody phony and he will never be able to be happy if he has no friends at all. The fact that he rejects everybody is definitely a huge factor influencing his fall. After leaving the bar, he walks back to the hotel. When he gets to the elevator, the elevator man asks Holden if he is interested in a prostitute. Without thinking, Holden says yes, his excuse to himself being that he was depressed. When she comes to his room, Holden ends up chickening out and becoming more depressed. Soon after she leaves, she comes back with the elevator man, Maurice. Maurice tells Holden that he owes the prostitute, Sunny, five more bucks. Holden argues but he ends up getting beat up while Sunny gets the money from his wallet.