Holden Caulfield is the son of wealthy parents. His family lives in New York City. He has an older brother, D.B., who "used to be a writer" but is now a screenwriter in Hollywood. He has a younger sister named Phoebe. His younger brother, Allie died recently of leukemia.
Holden has been to a series of all-male prep schools, and been kicked out of them one after another. He is now at Pencey Prep, and has recently been kicked out for not trying academically and missing class. In his final days at Pencey he gets into a fight with his roommate, Stradlater, over a girl, and also over a paper that Holden has written for Stradlater.
Though he is supposed to stay at Pencey until Wednesday, Holden leaves on the weekend before. Because he has money from his grandmother (and from selling his typewriter) he goes on a spree in New York.
He attempts to get a date with a stripper recommended by a friend, but he is rebuffed. At a hotel bar he spends time with three girls from Seattle, and finds the encounter disturbing and ultimately sad.
He goes onto a nightclub where he drinks a great deal and runs into a girl he knows. Later, as Holden goes up the elevator to his room in his hotel, he is offered a prostitute by the elevator operator.
Holden accepts, and a young and unsophisticated prostitute named Sunny comes to his room. She undresses, but Holden doesn't have the heart to go through with the encounter. He tries to talk to her about his feelings, but he cannot get through to her. Later he has an altercation with her pimp about the amount he is supposed to pay her. He feels humiliated by this experience.
The next day Holden takes a former girlfriend of his, Sally Hayes, to a Broadway show. He starts telling her of his troubles, which ultimately alienates her. They get into a fight, and they part. After more drinking, Holden finally goes home and wakes up his younger sister Phoebe. His parents are out at a party, and he manages to avoid being caught by them when they come home.
He goes to see a former teacher of his, Mr. Antolini. Holden tries to respond to Mr. Antolini's encouragement to get his life together, but it rings false. Eventually Mr. Antolini touches Holden in a way which Holden thinks is inappropriate, and he makes his excuses and gets out of there. He spends the rest of the night outdoors, and meets his sister again the next day. He tells her he is going to run away, but eventually he decides to go home. Because of his rough weekend Holden suffers a severe physical and mental breakdown, and at the end of the novel he is in a sanatorium or mental facility in California, being visited by his brother D.B.