All throughout the novel, "The Catcher in the Rye", but particularly in the second half of the book, Holden Caulfield experiences a series of relationships which follow a similar chaotic cycle, thus eventually bringing him to the point of mental illness. And while it can be argued that perhaps Holden was mentally ill before the sequence of events described (mainly because the novel takes place over just three days), it is quite obvious that in the last day that was narrated, he underwent a rapid and somewhat predictable breakdown.
Although on the very first page as well as in the last chapter Holden makes references to the fact that he is writing his story from a mental hospital/institution, he never comes right out to aware the reader of the situation that he is currently in. And this is quite understandable because Holden, throughout the novel, tries very much to create the illusion that it is he who is wonderful and everyone else who is phony. However, this is even more clever on the part of the author, Salinger, because by being very allusive to this point, it demands that the reader pays constant attention. For, one of the most important points to note in this novel is that the story is being told by a person who is not well neither physically or mentally, and if the reader can not determine this, they may take everything Holden says as the truth and will thus have a very clouded perception of the themes expressed by Salinger.
Along with the fact that the narrator is not a well person, it can be also misunderstood if and why Holden Caulfield undergoes a breakdown at the conclusion of the novel. This, too, may be something the reader does not pick up on because Holden never states this plainly either. And while the answer to the question "did Holden breakdown?" is obviously "yes", the question of how he broke down is not as easily answered. Although there are many reasons to how it happened, of which include Holden’s immense anger, as well as his attempts to isolate himself from society, what it basically came down to was uncontrollable depression.
And the reason why I mentioned earlier that this was rather predictable was because as the novel moved along, it seemed that more and more things began to depress him. For instance, early on it depressed him to think about Jane in a car with Stradlater which was understandable; then he mentioned how being too afraid to take his gloves back after someone stole them made him depressed (even though this never actually happened), which was a bit more alarming; and then (just to pick one example out of numerous ones), near the end, he found it depressing when Mr. Antolini simply yelled "good luck" to him as he was leaving. And that last example, more than any other was a great indicator of an eventual collapse because by no means should that have depressed him, and yet a shout of encouragement somehow had an opposite effect of what it was intended to have. And what this really showed was that the depression he was feeling began to build and build and it continued to wind itself in circles until it got to the point where the end of every other sentence read "man , that depressed me" or "god, that’s depressing". When this began to happen, as predicted by Mr. Antolini, it was obvious that Holden would not be able to sort his way through his problems on his own and that he was "riding for some kind of a terrible, terrible fall".
While many of the little observations that Holden made over the course of the novel went a long way towards thoroughly depressing him, it was the various relationships he had with either the same or opposite sexes that affected his depression the greatest. The general cycle that Holden went through was that he would, first of all, grow close to or try to grow close to a person in hopes of developing a meaningful relationship with them like he had had with both Allie and Phoebe. Next, what he would do was get himself to believe that he had achieved that type of relationship enough so that he could open up to the person and truly be himself. However, what he would then find was that he had greatly misjudged the relationship when the person rejected the only true thoughts Holden expressed in those three days. Finally, when he had realized his mistake, he would leave that person greatly depressed since he was unable to succeed with the relationship. However, he would still feel unfulfilled and so he would try all over again with someone else, all the while fooling himself into thinking that maybe this next one would workout better. And of course, this did not happen, and so he became more and more depressed, until he eventually broke down.
One of the most outstanding examples of exactly how this cycle progressed was in his date with Sally Hayes in chapter 17. Although he was never too excited about the date, he had spent some time that Sunday thinking about the times he had had with her and by taking her to a show he knew she would like, he demonstrated just how much he wanted things to work out between them. This came even more apparent when he presented the idea that they should get married and move away to new Hampshire together. And, as expected, she regarded him as if he were crazy and thus, Holden was let down again. And worst of all, he had upset her by telling her to shut up, finalizing the failure of the relationship. Then, proceeding that, he went to Phoebe, the only one who understood him, and he ended up upsetting her as well as himself. However, he eventually began to recognize this cycle and so this, undoubtedly, was the reason that he never met up with Jane. He was afraid the same thing would happen with her that had happened with all of the rest and so he did not contact her because by doing this, he at least had one relationship he could look back at as being untainted.
In my first journal entry for "The Catcher in the Rye", I addressed how it was very unlikely that Holden would ever admit that it was he who represented the problems in society, a prediction that would ultimately hold up. He avoided admitting just this by not telling the ending and by not telling outright where he was, and so it is obvious that Holden Caulfield, although perhaps the most notable fictional character ever, is also the most confused and disturbed.