In The Catcher in the Rye by J. D. Salinger, what are examples of Holden's success and failure to establish connections with other people?

Holden is a teenager who strives to be accepted by his peers just like any adolescent. Sometimes connections are made and sometimes they're not. That's just life. Holden mentions many different people with whom he comes into contact; and for the most part, he seems to struggle with creating meaningful connections with people without some sort of lie being involved. Whatever the relationship might be, though, Holden does connect with some people better than others. It is interesting to note, however, that Holden connects with older women best. For example, Holden seems to make a connection with Mrs. Morrow and a nun who is an English teacher; however, he fails to connect with his peers--Sally Hayes, Jane Gallagher, and Carl Luce.

Holden meets Mrs. Morrow in Chapter 8 on the train from Pencey to New York City. She is the mother of a former classmate named Ernest Morrow. Holden doesn't really like Ernest, but he has a delightful conversation with his mother. Holden lies and tells her that his name is Rudolf. He also lies by telling her that her son is popular, that other students wanted him to run for class president, but that he turned it down out of meekness and humility. Everything he says to her is a lie, practically, but he does get an invitation to her home to visit her son in the summer. This shows that she connected with Holden in a polite and social way. It also shows that Holden can carry on a polite conversation with someone and create a connection. 

Next, in Chapter 15, Holden connects with a nun who teaches English. They discuss novels and plays like Romeo and Juliet and both seem to connect intellectually. Holden is so impressed with this nun that he donates $10 to her. He accidentally blows cigarette smoke in her face at one point and feels terribly about it. If he didn't like her, he probably wouldn't have cared about that. Also, he feels guilty afterwards that he didn't donate more to her, which shows that he felt safe speaking with her and felt a connection. 

The peers that Holden attempts to connect with, but fails, are Sally, Jane and Carl. Holden goes on a date with Sally in Chapter 17. They make out, have a great time, and plan to decorate her Christmas tree; so, it would seem like they have a connection. Unfortunately, Holden obliterates any connection he has with Sally be freaking out on her. He not only makes up this plan to run away with her, but when she doesn't agree, he tells her, "C'mon, let's get outa here. . . You give me a royal pain in the ass, if you want to know the truth" (133). That does it. Sally makes her exit and Holden loses a good friend.

Jane Gallagher is a friend Holden is enamored with and thinks about consistently over the course of the story. He keeps saying that he is going to call her, but then backs out because he doesn't want to talk to her mother first. He anxiously wants to connect with her when he finds out that she goes out on a date with his roommate, but it never materializes because he is too afraid to call her. 

Finally, Carl Luce is an older and former classmate from Holden's time at Whooton. He meets him at an upper-class placed called the Wicker Bar. Holden is trying to fit in there with upper-class people as well as with Luce. It doesn't work. Holden tries so hard to get Carl interested in a conversation about women and psychology, but Carl seems resistant, if not annoyed. In the end, Holden says, "Old Luce. He was strictly a pain in the ass, but he certainly had a good vocabulary" (149). With those he doesn't connect with, it is because of some excuse based on either fear or rejection.