Chapter 17

Quote 1:"You ought to go to a boys' school sometime. Try it sometime," I said. "It's full of phonies, and all you do is study so that you can learn enough to be smart enough to be able to buy a goddam Cadillac some day, and you have to keep making believe you give a damn if the football team loses, and all you do is talk about girls and liquor and sex all day, and everybody sticks together in these dirty little goddam cliques. The guys that are on the basketball team stick together, the Catholics stick together, the goddam intellectuals stick together, the guys that play bridge stick together. Even the guys that belong to the goddam Book-of-the-Month Club stick together. If you try to have a little intelligent--" (ch.17) (T)
Quote 2:"We horsed around a little bit in the cab on the way over to the theater. At first she didn't want to, because she had her lipstick on and all, but I was being seductive as hell and she didn't have any alternative [...]." (ch.17)  (T)

Holden obviously didn't like school, he didn't really try in school, and he didn't have very many friends in school. Probably for this reason exactly because he thinks that they are all phonies, and not worth his time getting to know them. He obviously feels like he cannot fit into any of these social cliques because he may not have anything in common with them. Are we as readers supposed to feel bad for Holden? It is his own fault for not putting himself out there and selling his self to the people around him at Pency. Of course there is going to be cliques, it's high school, but people work through that.
Holden talks about his experience with women, and I think he thinks he is a guy with a lot of swagger and sex appeal. He had the confidence to call a hooker, and even later on in the book he calls a prostitute. He apparently isn't so smooth, he does take her on a romantic cheesy date. Then he end's up making her cry, and then he leaves without her, and even thinks about calling Jane. I don't think Holden is the type of guy to be in a committed stable relationship because he has never had one before. Although, his relationship with Phoebe is open and honest, it is different having a relationship with someone you like or love than a sister you love dearly.