Feeling terrible for running from Ernie’s, Holden walks 41 blocks back to his hotel, thinking about how he wished he still had the pair of gloves someone stole from him at Pencey. This causes him to reflect upon the fact that he’s somewhat cowardly when it comes to getting into fights. Although he likes to think he would fight the person who stole his gloves if given the chance, he knows he would do nothing but ask for them back, ultimately shying away from direct confrontation.
Holden’s feelings of cowardliness reflect his low self-esteem. While he doesn’t necessarily always hold himself to as high a standard as he holds other people in his life, this doesn’t mean that he has particularly good self-esteem. To that end, it becomes apparent in this moment that he tends to beat himself up for failing to behave in certain ways.
As Holden thinks about his lost gloves and his own cowardliness, he becomes more and more depressed. Because of this, he decides that he’d like to get drunk, noting that he’s capable of drinking quite a bit of liquor without getting sick. This, at least, is what happened when he and a friend at the Whooton School split a pint of scotch one night—although he puked before going to bed, he claims that this is because he forced himself to do it. With alcohol on his mind, he starts to enter a run-down bar but stops when two drunkards stumble outside. This deters him from entering, so he simply returns to the hotel.
In addition to the fact that Holden’s impulse to get drunk is an unhealthy way to deal with depression, it spotlights his escapist attitude. Rather than actually reflecting upon what’s bothering him, he wants to run away from his problems by getting drunk—a naïve idea, since turning to alcohol does nothing to actually address a person’s problems and, in some cases, can exacerbate feelings of depression. Preparing to step into the adult world of a New York City bar, he suddenly loses his nerve when he sees two haggard men stumble outside. That he decides to turn away after seeing this only indicates once more that he’s not quite ready or mature enough to enter certain adult situations.
While taking the elevator back to his hotel room, Holden meets Maurice, the elevator operator. Maurice offers to send a prostitute to his room for $5, and though he immediately regrets it, Holden accepts. At this point, he privately admits that he’s a virgin, though he’s had many chances to have sex. Every time he’s gotten the opportunity to lose his virginity, he says, something has happened to ruin the moment. He also suggests that he’s too attentive to girls’ feelings, unlike people like Stradlater, who work hard to convince their dates to have sex with them. Whenever a girl tells Holden to stop doing whatever he’s doing, he listens, feeling sorry for them because he thinks they’re “dumb.” For this reason, he decides that losing his virginity to a prostitute is probably a good idea, since it will allow him to simply get the experience over with.
Holden’s treatment of women is a bit confusing, since he approaches his romantic relationships with a mixture of condescending misogyny and—surprisingly—respect. On one hand, he doesn’t want to do anything with a woman if she doesn’t want to, setting him apart from people like Stradlater, who focus solely on their own physical desires. On the other hand, though, Holden says he doesn’t pressure women into having sex with him because he thinks they’re “dumb.” This is most likely an attempt to feel superior to his dates so that he doesn’t have to admit to himself that he’s intimidated by the prospect of having sex. Indeed, Holden thinks of himself as a “sex maniac,” but he hasn’t even lost his virginity. In an attempt to preserve his self-image as a mature adult, then, he condescendingly suggests that the reason he hasn’t had sex is because he feels so much more intelligent than his dates.
Back in his hotel room, Holden waits for Maurice to send a prostitute. Before long, a young woman named Sunny arrives. Holden is surprised to see that she doesn’t look much older than him and that she seems rather nervous. Treating her with extreme formality, he introduces himself as Jim Steele, and when she asks his age, he claims to be 22—a statement she challenges. This exchange depresses Holden, who suddenly feels very uninspired when Sunny undresses and sits on his lap. Asking if she feels like simply talking for a while, he tries to make small talk before eventually telling Sunny that he recently had an operation on his “clavichord,” which he says is embedded in the spinal canal. Because of this, he insists, he can’t have sex.
It is unsurprising that Holden doesn’t go through with his plan to have sex with a prostitute, since it’s clear that he’s quite nervous about engaging in sexual intercourse, which is a significant right of passage into adulthood. Even though he constantly postures as an adult, the truth of the matter is that he’s only a teenager yearning for a sense of acceptance and connection. If he can’t bring himself to have sex with somebody he knows, it’s extraordinarily unlikely that he’ll be able to convince himself to have sex with a prostitute, since this experience would no doubt be overwhelming to a young person who’s never become so intimate with another person. Furthermore, the lack of connection between Sunny and Holden emphasizes Holden’s overall loneliness, which is why he asks if she simply wants to talk. When she makes it clear that she’s uninterested in doing this, though, he finally lies and says he can’t have sex because he had an operation on his “clavichord,” which, despite what he says, is a small stringed keyboard popular in the Late Middle Ages.
Sunny is frustrated by Holden’s lack of sexual desire, telling him that Maurice woke her up specifically to meet him. Trying to calm her down, Holden assures her that he’ll still pay her for her time. He then hands her a $5 bill, but she claims he owes her $10. Refusing to pay more than the agreed-upon amount, he picks up her dress and hands it to her. After she gets dressed, she says, “So long, crumb-bum,” and leaves.
Holden agreed to have Maurice send a prostitute to his room because he was feeling lonely. Unfortunately, though, his time with Sunny has only emphasized the extent to which he feels alienated from his surroundings, since he can’t seem to connect with her on the level he wants (to be fair, this is because his attempts at conversation are out of place in this particular situation).