- Why do you think William Goldman chose to base The Princess Bride on an earlier "classic" novel that doesn't actually exist? What are the advantages?
- Which character do you feel the most sympathy for in this book? Why?
- What do you make of Goldman's relationship to his wife and son? Is it a good one? Please use specific examples from the text to support your argument.
- Why does Goldman keep interrupting the story to insert his own thoughts? Do these interruptions ruin or enhance the story? Why?
- What keeps Goldman so obsessed with The Princess Bride over so many years? What reasons does he give for why this particular story is so special?
- When is the story at its most exciting? When is it most boring? Do you think this is something Goldman does intentionally? Why or why not?
- What is Prince Humperdinck's biggest insecurity? What does it have to do with his "Zoo of Death"?
- What do you think really happens to Fezzik at the end of "Buttercup's Baby"? How does your version of the ending change the story as a whole?