When he arrives in New York City, Holden reaches out to a variety of people to try to feel less lonely. For instance, he has Maurice find him a prostitute. However, when the girl, Sunny, arrives, she seems so young and vulnerable that Holden only talks to her.
The next day, he calls up his friend Sally, who meets him in the city. They go ice-skating together, though he realizes the only reason she wants to ice skate is so that she can wear one of the cute little blue ice-skating outfits that only covers her rear end. They go out afterward, but Holden's attempts to break through to real communication don't go well. She asks again if he is going to help trim her Christmas tree, which irritates him, as he already has repeatedly assured her he would. When he suggests they run off together, she, in turn, gets annoyed.
Holden sneaks into his parents' apartment to see his little sister, Phoebe, and while she gets irate with him for flunking out of school and being too negative, he is glad to see her. They have a good time together dancing, and he gives her his hunting cap.
He then decides to go see his old teacher, Mr. Antolini, and his wife. The Antolinis are part of Holden's parents' upper-class social set, and they invite him to spend the night. However, when Mr. Antolini makes a dubious pass at Holden by coming to him and stroking his hair, Holden leaves.
Holden makes a number of efforts to reach out to people. Most don't work out too well, but he is trying to connect, if often not always going about it in the best way.