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Holden walks back towards his hotel in the cold, lamenting the loss of his gloves, which he thinks were stolen by someone at Pencey. To regain some of his warmth, Holden puts on his hunting hat and decides to stop in another bar. He changes his mind when he sees two tough looking guys emerging from the bar.
Back at the hotel, Holden is solicited by the elevator operator, Maurice, who promises to send him a prostitute in fifteen minutes. Holden agrees to the offer, but regrets his decision almost immediately. He cleans up and then paces nervously around the room, waiting for the girl. Sunny soon arrives, and Holden introduces himself as Jim Steele. He tries to act suave, but no matter how hard he tries, Holden, still a virgin, is still extremely uncomfortable. The girl’s businesslike manner only makes him feel more awkward. When he tries to strike up a conversation, Sunny wants to know what he is waiting for. She sits on his lap and tries to seduce him. It is more than Holden can handle. He apologizes, pays her five dollars, and tells her to leave. Sunny tells Holden the price is ten dollars. He refuses to pay her more than he agreed on with Maurice, and she leaves with an insult and a veiled threat.
This chapter reveals several new aspects of Holden’s personality. When he is walking in the cold, he comments that someone at Pencey probably stole his gloves. He imagines what he would have said if he had caught the thief. Then he is honest with himself and admits he would probably say very little since he is a coward at heart. Rather than punch the thief and accuse him openly, Holden says he would have attacked him with sarcasm. The fact that two guys coming out of a bar is enough to discourage Holden from going in is further proof of his cowardice. But his cowardice is fed by the fact that he is weak and never wins in a fight, as seen in an earlier chapter.
Another example of Holden’s fear occurs in the scene when Holden agrees to let the elevator operator get him a prostitute. Instantly he regrets his decision since he is a virgin. Inexperience and fear assail him in his hotel room as he tries to prepare himself for her visit. He tries to strengthen his resolve by telling himself that the prostitute will be good practice if he ever decides to marry. He also imagines himself becoming like Monsieur Blake, a fictional character in a book he once read. Monsieur Blake was a charming and sophisticated rake, ruthlessly getting what he wanted from women.
Holden tries to be suave with the prostitute, introducing himself as Jim Steele. His nervousness, however, gets in the way, and he trips over his suitcase. He finds himself unable to take action and tells Sunny he just wants to talk. He tries desperately to engage her in some meaningful dialogue, but she grows frustrated, sits on his lap, and tries to seduce him. To get out of the bad situation, he finally tells the prostitute that he is unable to have sex because he is recovering from an operation on his "clavichord." He pays her the agreed amount of five dollars, but she demands ten. When he refuses, she threatens him and leaves.