As we get into the later chapters of the novel, we start to see a exactly what emotional state Holden is really in. In chapters 15 and 16, we see the usual Holden as he makes a date with an old friend Sally, comes in contact with two nuns whom he befriends, and rambles on about phonies once again and their cheap suitcases, and then goes on to talk about his hatred for movies and the phony actors who play in them. However, for a brief moment in chapter 16 we see a glimpse of Holden’s appreciative side when he sees a church going family and a little boy singing a song, and he finds this innocent and pure. After this moment we start seeing more uncontrollable fluctuation of his emotions and throughout the next chapters his fragile mental side seems to show more frequently. This especially becomes prevalent in chapter 17.
In chapter 17, Holden goes on his date with Sally. The date at first seems innocent as they see a theatre show, and then go ice skating while Holden admires her and complains about his sore ankles. However, when they both sit down, their conversation becomes rather heated. Holden is complaining about all the phonies from his school (in a much more fiery way) and how he feels rejected and almost alienated, and he then suggests that he and Sally run away together to a “cabin in the woods.” Sally obviously claims that the notion is ridiculous and insults him. Holden then becomes angry with her and starts yelling without being aware of it, calls her a pain in the ass, and finally making her cry. He tries to turn the situation around, but it is too late and he leaves her at the ice rink.
This chapter really starts to show how emotionally unstable Holden is, and how detached from reality he is, which leads him on an aimless journey to a drug store, and then to a bar where he meets his old friend Luce, from Whooton. After trying to talk about sexual things with Luce, Holden finds himself alone once again when his friend becomes so annoyed with him that he leaves the bar. At this point, Holden has been “alienated” by two of his friends within hours of each other, and this is what arguably leads him to become drunk and wonder to the pond where he first inquired about the ducks. These chapters seem to highlight Holden’s complete solitude from his friends and even life. Holden Caulfield seems to be on a downward spiral towards emotional breakdown.