Holden has a complicated relationship with girls and women that threads throughout the novel. There are the girls he wants to protect, such as Jane Gallagher, a family friend with whom he enjoys playing checkers. She falls into the category of girls like his little sister, Phoebe, who need to be guarded from the world's predators. Therefore, when Holden finds out his roommate, Stradlater, a smooth talker who seduces girls, is taking Jane on a date, Holden becomes agitated:
I kept thinking about Jane, and about Stradlater having a date with her and all. It made me so nervous I nearly went crazy.
By the time Stradlater comes back, Holden is so upset he gets into a fist fight with him, which leads to him leaving Pencey in the middle of the night for New York City.
However, Holden also longs for a girl as a romantic partner he can share his life with. Even though he thinks she is an insufferable phony, he invites Sally Hayes on a date in Manhattan. His conflicted thinking comes out when he sees her:
Finally, old Sally started coming up the stairs, and I started down to meet her. She looked terrific. She really did. She had on this black coat and sort of a black beret. She hardly ever wore a hat, but that beret looked nice. The funny part is, I felt like marrying her the minute I saw her. I'm crazy. I didn't even like her much, and yet all of a sudden I felt like I was in love with her and wanted to marry her.
Holden, who is a virgin, also thinks of girls as sex objects and would like to experience sex, but when he hires a prostitute he is too kindhearted to sleep with her, so they talk instead.
Holden is kind to the nuns he meets while having breakfast in a diner, giving them ten dollars—the equivalent of about a hundred in today's money. They fall into his protected category of "pure" women.
While Holden has imbibed some of his society's sexism, his general sense of empathy causes him to treat even women who might be generally thought of as less "pure" with kindness—and to long for companionship even with a girl like Sally, whom he half despises.
Holden's view of women in general is not too kind. He doesn't feel that they are smart, nor hold any depth of character. He believed that women would just be driven by instinct and just go out with guys for the money. He felt this way mainly because that was the sort of women he was hanging with, and because he tends to generalize.
An example of Holden's issue with women is illustrated in the following paragraph on Ch. 13
I mean most girls are so dumb and all. After you neck them for a while, you can really watch them losing their brains. You take a girl when she really gets passionate, she just hasn't any brains.
Nevertheless, he holds a very intense respect and love for his little sister, Phoebe. She acts almost like an opposite to him, since she appears to be more sociable and people-friendly than him. He is quite attached to her and separates her from the rest of the world. She is the only person that Holden is connected to psychologically.
When tackling this question we must first recognize that Holden is a lost, confused, and immature teenage boy.
Like most everyone else in society, Holden sees women as phony. He believes they are only interested in superficial materialism and image. For example, when Holden takes Sally on a date, he is disgusted with her when she goes to talk to another boy. He assumes she only does so because he is "ivy league":
Then all of a sudden, she saw some jerk she knew on the other side of the lobby. Some guy in one of those very dark gray flannel suits and one of those checkered vests. Strictly Ivy League. Big deal. He was standing next to the wall, smoking himself to death and looking bored as hell. Old Sally kept saying, "I know that boy from somewhere." [...] The jerk noticed her and came over and said hello. You should've seen the way they said hello. You'd have thought they hadn't seen each other in twenty years. You'd have thought they'd taken baths in the same bathtub or something when they were little kids. Old buddyroos. It was nauseating. The funny part was, they probably met each other just once, at some phony party [...] The worst part was, the jerk had one of those very phony, Ivy League voices, one of those very tired, snobby voices.
Holden believes Sally's only motivation in going to talk to this boy is his social status. He believes she is drawing attention to herself so other people in the room will see that she is speaking to a desirable man.
This is just one of many examples. You may also want to consider:
- Holden's interactions with the 3 women at the bar in chapter 9
- The beginning of chapter 17 as Holden sits in the hotel lobby
- His opinion of Sunny, the prostitute in chapter 13
- Also, don't forget about Jane. However, do note, she is the exception, not the rule.
Hope this helps!