In Catcher in the Rye, who did Holden try to sexually advance on, but did not carry it out? And who were examples of people that Holden tried to alienate himself from?
Holden tries to alienate himself from just about everybody. The list would be shorter if you asked who does Holden not alienate himself from. I can only think of one character for sure that Holden genuinely enjoys being around, wants to spend time with, and isn't willing to run away from. That would be his sister, Phoebe. You might include Jane in that list, but she never actually appears in the novel, so I don't think that she is a good choice. Holden alienates just about everybody else. He alienates his roommate, Stradlater as well as his hall neighbor Ackley. Holden also intentionally distances himself from adults as well. Throughout the novel he avoids his own family and distances himself from Mr. Spencer, who was the only teacher that Holden liked in the first place.
Holden tried to make sexual advances with Sunny, a prostitute. He could not carry through with it though, because he began seeing her as a person instead of a sexual object.
"I'll pay you and all, but do you mind very much if we don't do it? Do you mind very much?" The trouble was, I just didn't want to do it. I felt more depressed than sexy, if you want to know the truth. She was depressing. Her green dress hanging in the closet and all.