In Chapter 8 of The Catcher in the Rye, as he is leaving Pencey for New York City, Holden meets the mother of another Pencey Prep student on the train. She is about forty years old. He feels sexually attracted to her but also protective. He lies to her about her son, who is a jerk, so that she will feel good about him. But the pressure to appear masculine in front of a good-looking woman takes over, and Holden tries to pick her up, saying:

"Would you care for a cocktail?" I asked her. I was feeling in the mood for one myself. "We can go in the club car. All right?"

Holden most likely wants a drink because he is feeling uncertain about the role he is playing and the masculinity he is trying to exude.

In Chapter 13, Holden thinks about why he has hired a prostitute. As he gets ready to meet the prostitute, who is being sent to his hotel room, Holden thinks about his anxiety over women and his desire to be able to perform sexually in a suave and competent way. These standards of masculinity, in which a man is expected to be sexually knowledgeable, worry him. He would like to stay in a state of child-like innocence, but at the same time, he is caught in a world where he feels intense pressure to be able to perform sexually and be able to play a woman like a violin:

In a way, that's why I sort of wanted to get some practice in, in case I ever get married. Caulfield and his Magic Violin, boy. It's corny, I realize, but it isn't too corny. I wouldn't mind being pretty good at that stuff.

Later, Holden's concern with being seen as masculine by Luce at the bar comes out when he lies and implies he is sexually active when he has previously confessed to the readers that he is a virgin. When Luce says sex is both spiritual and physical to him, Holden agrees that it is like that for him too:

"So do I! So do I regard it as a wuddayacallit—a physical and spiritual experience and all. I really do. But it depends on who the hell I'm doing it with. If I'm doing it with somebody I don't even—"

Holden is so afraid of losing face in front of another man that he pretends to a level of sexual experience he does not have.