I think
Holden wanted to be an
optimist, but kept getting confounded at every turn.
From The Catcher in the Rye, pp.202:
"I went down by a different staircase, and I saw another 'Fuck you' on the wall. I tried to rub it off with my hand again, but this one was scratched on, with a knife or something. It wouldn't come off. It's hopeless, anyway. If you had a million years to do it in, you couldn't rub out even half the 'Fuck you' signs in the world. It's impossible."
From The Catcher in the Rye, pp.204:
"That's the whole trouble. You can't ever find a place that's nice and peaceful, because there isn't any. You may think there is, but once you get there, when you're not looking, somebody'll sneak up and write 'Fuck you' right under your nose. Try it sometime. I think, even, if I ever die, and they stick me in a cemetary, and I have a tombstone and all, it'll say 'Holden Caulfield' on it, and then what year I was born and what year I died, and then right under that it'll say 'Fuck you.' I'm positive, in fact."
This passage, I believe, has the most telling detail of Holden's inner life than any other from the entire book- the bit where he says "...if I ever die..." as opposed to, "...when I die."