1. Think about Holden’s vision of the nature of childhood and adulthood. Are the two realms as separate as Holden believes them to be? Where does he fit in?
2. The novel is structured around Holden’s encounters and interactions with other people. Does any pattern seem to emerge, or does anything change in his interactions as the novel progresses? How do Holden’s encounters with adults, children, women, and his peers evolve as the novel progresses?
3. Throughout the book, Holden longs for intimacy with other human beings. Discuss the different types of relationships Holden attempts and the different types of intimacy in the book. What is the role of sexuality in The Catcher in the Rye? How do Holden’s sexual relationships differ from his nonsexual encounters?
4. The most ambiguous encounter in the book is Holden’s night at Mr. Antolini’s apartment. What do you make of Mr. Antolini’s actions? Was he making a pass at Holden? What is the significance of his actions, and how do they relate to his role as someone trying to prevent Holden from “taking a fall”?
5. Holden often behaves like a prophet or a saint, pointing out the phoniness and wickedness in the world around him. Is Holden as perfect as he wants to be? Are there instances where he is phony and full of hypocrisy? What do these moments reveal about his character and his psychological problems?