Would Holden like Lee Fiora from Prep?
I think that Holden could show some level of attraction and even "like" towards Lee. Where there would be friction is that both of them operate from different starting points. Holden really has no desire to be accepted by the people at Pencey. Even if one makes the argument that Holden is manifesting anger and resentment because of rejection, it's hard to make a case that Holden holds feelings of desire in being accepted. Lee truly does want to find some acceptance at Ault. Lee looks at life at the Ault School as a chance to escape the economic and social challenges of Indiana. This is a dimension that Holden never really has to accept. Money and social standing were never challenges for Holden. It becomes clear that Holden's parents are individuals of means and of wealth, something that Lee is not. This difference might be reflective of how both of them are at different points in the social acceptance spectrum. Lee seeks acceptance in her prep school setting, while Holden is not really motivated by such a condition.
Both characters would find some level of common ground on the hypocrisy in the social orders at both of their schools. They are both insightful and could find some level of discourse in this regard. It might be interesting to see Holden actually voice a positive opinion about someone who is in the same ballpark as he is in terms of struggling with acceptance and identity. One could see how Holden would get along with someone like Lee. I think that it might be interesting to analyze if Lee would like someone like Holden.