1. Hilary participates in a bet with his classmates that he won’t last three terms at St. Oswald’s school. What distinguishes him from the other boys at St. Oswald’s and what keeps him from fitting in?

2. Hilary’s world at boarding school is confining, cold, and at times, brutal. Finn’s world, despite its physical dangers and harsh economic reality, seems liberating to Hilary. Is he romanticizing Finn’s life or is Finn’s life truly freer?

3. On first glimpse, Hilary is struck immediately by the mysterious figure of Finn on the beach and describes the vision as looking into the mirror at someone he’d always hoped to be. What does Finn represent to Hilary and how is it different from Hilary’s own image of himself? How are they similar?

4. As the older Hilary looks back on his life, he evokes an image of himself that is at once sharply insightful, darkly cynical, and, at times, naïve. What are some of his blind spots? What does he see as an adult that he could not see as a teenager?

5. The reader has little access to Finn’s thoughts throughout the novel. What do you think Finn gets out of his relationship with Hilary?

6. From Hilary’s perspective, formal schooling is mostly useless and serves only to cement students’ social status and privileges. Finn, on the other hand, is self-taught. What sort of education does Hilary get from his adventures with Finn?

7. Hilary often complains about the constant and needy presence of his schoolmate Reese. What is Reese’s role in this story? What, if anything, does he teach Hilary?

8. Hilary is interested in the history of the land and the book is strewn with descriptions of the changing coastline and tides. What is the significance of these passages? How does Hilary’s idea of history change over time?

9. At the book’s climax, Finn reveals that he’s not who Hilary thought he was. Was Hilary responsible for failing to see the real Finn? Would Hilary have been as infatuated with Finn had he known the truth all along?

10. Hilary is ultimately found not guilty of any crimes. Is he guilty of any moral offenses? Or are the events of the novel simply a result of him being confused and young?

11. Hilary is consumed with the desire to be Finn, and little-by-little he transforms himself in Finn’s image. To what extent is identity shaped by close relationships like these? Has Hilary’s identity changed by the end of the story?