Holden struggles in several different areas throughout the novel. Externally, Holden struggles with his school work. He is failing every class except English at Pency, which is why he is not allowed back for the next term. Holden also has a litany of social problems. He struggles to maintain genuine friendships with other boys his age and is often highly critical of those around him. Holden portrays his hypocritical nature by continually insulting and criticizing his acquaintances while refusing to analyze his own behavior. Holden also struggles to develop relationships with women throughout the novel. He lacks the ability to communicate with Jane Gallagher and does not express empathy towards Sally Hayes. Holden's struggles can be attributed to the loss of his younger brother Allie. Since Allie's death, Holden has struggled to move on with his life. He cannot come to terms with his future and instead lives in the idyllic past when Allie was alive. Holden's fear of becoming an adult comes from his inability to move on after Allie's death. His phycological issues negatively affect his relationships, perspective, and attitude throughout the novel.
Holden struggles are with relationships, both with people and with himself. When we look at other people, the struggle with relationships is evident through his interactions with his roommate when he says he is going on a date with Jane Gallagher.
"Jane Gallagher. Jesus. I couldn’t get her off my mind. I really couldn’t. I oughta go down and say hello to her, at least.”
Holden has a clear interest in Jane, but he cannot bring himself to go down and say hello to her. Throughout the rest of the story his interest in Jane is clear, yet he cannot bring himself to ever call her.
He also struggles with family and class expectations. Growing up in an upper-middle class family, both his family and his economic class expect him to succeed at a prestigious prep school and then go on to attend an ivy league college. This scares Holden so he plans spontaneous fantasies that will not work, like running away with Sally (which scares her) and running west to live with a deaf mute.