Holden Caufield is phoning his Teacher, Mr. Antolini, from his family's apartment, as Chapter 23 begins. It is still in the early morning hours of Monday morning. Mr. Antolini is very kind to Holden after discovering that Holden has flunked out of yet another school. He tells Holden to "come right over."

Holden wants to see Mr. Antolini because he has developed a close relationship with him through the years. Mr. Antolini was a teacher from one of his schools called Elkton Hills but has since moved to New York. Perhaps Holden decides to call him because he was recently thinking about James Castle, the boy who threw himself out of a window at Elkton Hills. Holden tells us that it was Mr. Antolini who finally picked up James's lifeless body and carried him to the infirmary, despite getting covered with James's blood on the way there. Holden believes that Mr. Antolini is an authentic, caring teacher.

Phoebe is sitting on the bed "with her legs folded like one of those yogi guys," when Holden comes back into D.B.'s room. Holden uses this as an example of how "she kills me." He uses that expression again when he tells us that she freezes and doesn't move a bit, in-between songs when they are dancing. Holden taught Phoebe how to dance a few years ago, but says she got advanced on her own. The two dance together and one can imagine the tall Holden dancing with his much shorter little sister, as he tells us how well she can follow his lead, despite their size differences.

After demonstrating to Holden, how she can fake a fever, the two hear their parents coming into the apartment. Holden quickly hides in the closet. When Mrs. Caufield enters the room, she is very motherly towards Phoebe. She asks her why she is still awake, if she liked her dinner, if she is warm enough and does she need another blanket. She also notices the smell of Holden's cigarette smoke in the room. She asks Phoebe if she was smoking a cigarette and Phoebe tells her she did smoke a cigarette but only took one drag and threw it out the window. Mrs. Caufield says, "I don't like that all, Phoebe. I don't like that at all." Finally, she leaves the room, and Holden comes out of the closet. He tells Phoebe he has to get going. He asks her if she has any money he can borrow, and is moved to tears when she gives him all of her Christmas stash; $8.65. She tells Holden if he leaves, he will not be able to see her in her Christmas play. Holden says he will not go to Colorado to be a Ranch worker, until after he sees her in the Christmas play. As Holden is leaving, he suddenly starts crying. He tells us he is crying so hard that he cannot even stop. Phoebe becomes frightened for her brother. So, Holden gives Phoebe his red hunting cap. He tells us he is sure she will like it because she likes unique things like that. Holden says he bets she will even put it on after he leaves, and sleep in it.

Holden makes some noise when he is sneaking out of the apartment, but tells us he does not even care anymore. He says, "I figured if they caught me, they caught me. I almost wish they did, in a way." However, Holden's parents do now wake up, and he manages to get out of the apartment without being discovered.

When Holden arrives at Mr. Antaloni's lavish apartment, he tells us that he has been there many times before. Mr. Antaloni is now a family friend. He had come to dinner at the Caufields' many times just to see how Holden was doing. Holden tells us that he played tennis with Mr. Antaloni and his wife a few times at their tennis club in Forest Hills. Holden tells us that Mr. Antaloni married into money and that his wife is also "about sixty years older than Mr. Antaloni. But they seemed to get along quite well."

When Mr. Antaloni greets Holden, he has been drinking heavily. The couple had a party earlier in the evening, and, while Mrs. Antaloni is drinking coffee, Mr. Antaloni is still drinking Highballs.

Mr. Antaloni asks Holden what happened at Pencey. Holden assures him that he did not fail English. He complains about an Oral Expressions course he took and failed because they do not allow digressions. Holden feels that digressions are the spice of life. He likes it when somebody is telling a story and he or she goes off on a tangent. Holden says it is more authentic when a person gets caught up in something, and it also lets him know more about their character. Mr. Antaloni says, "there is a time and a place for everything." He disagrees with Holden. Holden starts getting sick of Mr. Antaloni's witty remarks and his desire to talk about academics.

Holden is not just getting sick of Mr. Antaloni but is also just plain getting sick. He has not eaten much or slept more than a few hours in the past few days. Holden is also going through a very traumatic time because he has flunked out of yet another school. While he is not aware of how upset he is about having to tell his parents this bad news, it is taking a heavy emotional toll.

Mr. Antaloni, though he is drunk, is waxing poetic about the value of education. He tells Holden that he has the sense that Holden is headed for disaster. He warns that if Holden does not start to get excited about something and put all his energies into that thing that inspires him, he will meet with disaster. Holden is struggling not to yawn; he does not want to be rude because it is obvious that his teacher is very concerned about the direction that Holden's life is taking at this point. However, finally, Holden cannot resist letting out a big yawn, and Mr. Antaloni takes the hint. The two make up the couch for Holden to go to sleep. Mr. Antaloni wants to keep drinking though and tells Holden he will be in the kitchen for a while.

Holden is so exhausted he immediately falls into a deep sleep. He wakes up because he feels a hand stroking his hair. Holden is jolted awake, and he sees that his teacher is sitting on the floor next to him, and he is stroking Holden's hair. Holden screams and asks his teacher what he thinks he is doing? In Holden's mind, his teacher is a pervert. He is terrified and disgusted by this thought. On the other hand, Mr. Antaloni remains very calm and acts as if nothing unusual has taken place. Holden jumps up and gets dressed. He tells his teacher that he has to go to get his suitcase from the locker at Grand Central Station. He assures Mr. Antaloni that he will come right back. Mr. Antaloni tries to dissuade Holden from leaving as it is still dark outside, but Holden insists.

Holden is certain that Mr. Antaloni was trying to make a homosexual advance on him. Holden describes this as being "perverty." He says things like this have happened to him about twenty times in his life and he cannot stand them. His heart is beating wildly, and he cannot stop sweating.

In these two chapters, we see that Holden is scared of facing his parents with the fact that he has flunked out of Pensey. Holden does have a respite from all of this anxiety when he spends some time with Phoebe. When Phoebe voices the fear that Holden's father will "kill him." Holden hatches a plan to go to Colorado and work on a ranch. Phoebe tells him that is not realistic because he does not even know how to ride a horse. Holden eludes his parents when they come back to the apartment from a party and goes over to one of his favorite teacher's house. Holden does admit he almost hoped his parents would catch him at home with Phoebe. It seems unfortunate for Holden that they do not wake up.

In Chapter 24, Mr. Antaloni has been celebrating at a Holiday party and wants to keep the party buzz going by continuing to drink well into the visit from Holden. Holden's perception that his teacher was inappropriate with him is not stated as an actual attempt by Mr. Antaloni to molest Holden. Although Holden perceives it as such, it could be that Mr. Antaloni was just drunk and being fatherly by patting Holden's head. One thing that is obvious is that Mr. Antaloni is very concerned about Holden.