Holden is everybody's favorite judgmental cynic. He also has a bit of a problem: he's completely alone and he knows it – we stopped count at about 22 when we tried to track the number of times he admits to being lonely. The clear conflict here is that he judges and hates everyone, but at the same time wants them to join him for a drink and chat it up for the evening. He seems perpetually caught in this very limbo: judging a person, making a half-hearted attempt to reach out, and then being disappointed when that person isn't there to support him, talk with him, or try to understand him.
Often, Holden can't even get to the point of reaching out at all. His passivity and indecision take over at key moments. Check out the very first thing he does when he gets off the train in New York City – he goes into a phone booth. He knows he wants to call someone, but proceeds to veto all of his options: D.B. is in Hollywood, Phoebe is sleeping, he "doesn't feel like" calling Jane's mother, he's afraid Sally's mom will pick up at her house, and he "doesn't like" Carl Luce. Holden steps out of the phone booth after twenty minutes, having not called anyone. This is the story of his life. Or at least the story of The Catcher in the Rye.
When Holden does end up interacting with people, he usually gets the short end of the stick. He invites Ackley along to the movies, but Ackley won't return the favor by letting Holden sleep in his roommate's bed. He writes Stradlater's composition for him, and in return gets yelled at (and socked in the nose, but technically that was for different reasons). He even had to type that essay on a junky old typewriter because he had lent his own to the guy down the hall. He gives up his hound's-tooth jacket for the night, knowing it'll get stretched out in the shoulders. He gets stuck with the tab for the three "moronic" girls' drinks in the Lavender Room at his hotel. He pays Sunny even though he doesn't have sex with her, and ends up getting cheated out of five more dollars (and socked in the stomach, although technically this, too, was for different reasons).
Despite all this instances, Holden never makes himself out to be a victim. He doesn't seem to notice that he gets taken advantage of – repeatedly. This is part of his own youth and naïveté. Despite his judgmental exterior, Holden is surprisingly eager to please – and to make friends.
OK, but how can Holden be enthusiastic about meeting people when he deems everyone and their mother (literally – he encounters quite a few mothers in this story) to be phony? In his mind, everyone is a social-climber, a name-dropper, appearance-obsessed, a secret slob, a private flit, or a suck-up. Holden finds any semblance of normal adult life to be "phony." He doesn't want to grow up and get a job and play golf and drink martinis and go to an office. and he certainly doesn't want anything to do with the "bastards" that do. Except that, really, he sort of does. So what's the catch?
Basically, if Holden calls everyone a phony, he can feel better when they reject him. It's not his fault the three girls in the Lavender Room weren't terribly interested in giving him the time of day; they were just phonies who couldn't carry on a conversation. He can't feel bad if Ackley doesn't want to let him stay and chat; Ackley's just a pimply moron. If Stradlater doesn't want to hang out, it's because he's a jerk. We prefer not to use tired, old terms like "defense mechanism," but we're certainly tempted to in this case.
So far, Holden doesn't sound too different from a typical, disaffected youth. We all know people like this. We've probably all felt like this at one point or another. But there are definite hints in the text that Holden isn't just another normal teenager.
For one, we know he had to take some sort of "rest" from regular life to go through therapy and get psychoanalyzed. We know he's prone to violent outbreaks, like breaking all the windows in the garage the night Allie died, or tackling Stradlater after his date with Jane, or screaming at Sally in public (he claims he's not yelling, but she repeatedly asks him to "stop screaming" at her). He's flunked out of multiple boarding schools. He's admittedly depressed all the time.
By the end of the novel, Holden's depression/anger starts to take physical form: he's nauseous, he has a headache, he feels dizzy, and he eventually passes out. His comments at the beginning of the novel suggest that his breakdown or whatnot was in fact physical: he says he "practically got t.b. and came out here for all these goddam check-ups and stuff." So we can pretty sure there's something up with Holden – something more than average teenage disillusionment.
One way we can understand Holden's abnormality is to look at the traumatic events in his childhood, most importantly the death of his brother Allie. Holden's confession that he broke all the windows in the garage the night Allie died is an important one – it tells us right off the bat that Allie's death has had a huge impact on Holden's life. That Allie pops up over and over throughout the course of the narrative confirms this. The death of James Castle, too, seems to be significant, since it was the second time Holden had a close and personal encounter with death.
Because of these events, Holden is plagued with thoughts of mortality. Half the symbols we discuss in "Symbols, Imagery, Allegory" have to do with death.
The way Holden deals with his own mortality is interesting. At times he is self-destructive and seems to possess almost a death wish. After all, he talks about suicide after the Maurice and Sunny (prostitute) incident, and he says he'd volunteer to sit on top of the next atomic bomb. Other times, he seems terrified at the thought of his own death, as when he prays to Allie while crossing the street not to let him disappear. Even more strange, he's sometimes indifferent and objective to the notion, like when he sits in the freezing cold park after looking for the ducks and wonders what his family would think and what his funeral would be like if he got pneumonia and died. Such morbid thoughts do color the way Holden sees the world, and we're guessing they are at least partially responsible for his jaded cynicism.
Of course, you can't talk about Holden Caulfield without talking about sex. We'd like to start with Holden's hugely revealing digression in Chapter Nine. The digression is spurred on by the scenes Holden witnesses looking out of his hotel window into other rooms, namely, a "distinguished-looking" man prancing about in women's clothes, and a couple squirting water or highballs or something into each other's mouths. Holden declares the hotel is "full of perverts" and launches into his thoughts on sex and perverts in general. His problem, he admits, is that if you really like a girl, you wouldn't want to "do crumby stuff" to her.
It looks as though Holden sees sex as inherently degrading, no matter how it's done. If he cares about a girl, like Jane for instance, he can't have a sexual relationship with her because it would turn her into an object. This means Holden has to either fulfill his sexual urges with girls he doesn't care about, or not fulfill them at all.
Holden's second problem, he says, is that when he's fooling around with a girl and she suggests they stop, he actually stops. Other guys, he says, just keep going, but Holden actually stops. As we talk about in Stradlater's "Character Analysis," Holden isn't really talking about rape. Keep in mind that this is 1951 and before today's levels of sensitivity. Remember Holden's earlier argument about sex being somehow degrading; he can't find a balance between respecting a woman (and her saying "no") and taking sexual control of a situation where – maybe – the woman wants him to.
Moving on to our other sensitive topic, we have to cover the issue of sexual molestation with regards to Holden and Jane. We go into the nuanced, argumentative details in Mr. Antolini's "Character Analysis" and also in Jane's, but what does it mean for Holden? He either did or did not experience a come-on at the hands of his former teacher, and he either did or did not have "perverty" stuff happen to him "about twenty times since [he] was a kid." And Jane either did or did not get molested by her stepfather.
Why all this ambiguity? Can't you just tell us what's going on!? Well, yes, an omniscient, third-person narrator could. But the fact is, Holden isn't sure. The Antolini incident, much like the situation with Jane and her stepfather, is ambiguous. Why? Because all this sex stuff is often ambiguous. Especially when you're sixteen. This ambiguity is what makes sex so confusing to Holden, who openly admits he "just [doesn't] understand it."
Lastly, there's a theory out there that Holden is gay. That's one solution to why he feels confused and alienated and so forth. If you want to argue for this theory, pay attention to the way Holden often focuses on the physicality of the male body (like with Stradlater, Ackley, or Mr. Spencer). You could say he reads homosexuality into others when it actually may not be there (like Carl Luce or Mr. Antolini). And he's not comfortable with the thought of having sex with a woman.
If you want some gory details on Holden's view of religion, check out the "Character Analysis" on the two nuns. For now we'll just say that Holden dislikes money and religion for the same reason – they create social barriers between people. Education isn't too far off that mark, either, since it's part of classism.
We also think Holden views religion and education similarly, since he doesn't seem to have a problem with personal spirituality or the pursuit of knowledge per se, but rather is upset at the institutions that promote them. In other words, believing in God would be fine if there weren't rules and people (like "phony" priests) trying to tell you what to think. And learning would be fine (look at the way Holden talks about books) if there weren't all these rules and people (like teachers) telling you what to think. See the connection?
Speaking of knowledge, we happen to be under the impression that Holden is one wise kid. Sure, he says he's not that intelligent, and he keeps failing all his classes, and some call him "ignorant" and "troubled," but when you actually read The Catcher in the Rye, you'll see that Holden comes up with a slew of Yoda-like statements that really knock our socks off. Examples:
Last and certainly not least, let's talk about Holden's grand ambition to be…the catcher in the rye. We already talked about the irony here in "What's Up With the Title?" So you already know the deal: Holden's ambitions = impossible. There are just too many "Fuck you" signs in the world.
But why does he have this fantasy in the first place? Why is Holden so obsessed with innocence? To answer this question, you have to take into account e-v-e-r-y-t-h-i-n-g we just said up there in Holden's "Character Analysis." That's why we put this section last. Does it have to do with his feelings on and past (bad) experiences with sexuality? Probably. Does it also have to do with the fact that Allie died when he was ten years old? It's highly likely. Is it related to Holden's feelings on adult phoniness, his brewing madness, his emotional intelligence and eschewing of societal constructs? We think yes, sure thing, and indeed. But we're done here. It's all you now – take it away.