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- In The Princess Bride, at the very end, the Grandson asks the Grandfather to come back and read the story again. The Grandfather replies, "As you wish," which seems very sweet but not particularly dramatic—until you remember what was said earlier: "When he said 'As you wish,' what he meant was 'I love you.' "
- After Inigo Montoya got his Heroic Second Wind, he took control of the duel so thoroughly that he was able to give Count Rugen exactly the same wounds Rugen gave him.
- To explain how smart he is, Vizzini describes Plato, Aristotle, and Socrates as "morons." Maybe if he had spent some time studying the Ancient Greeks instead of belittling them, he would have learned about the art of building immunity to poison.
- When The Man in Black asks Vizzini about the poison, he actually says "Where is the poison?" not "Which goblet has the poison?" Vizzini should have said that he'd drink from the bottle.
- Before their duel Inigo tells The Man In Black that "There's not a lot of money in revenge." Only later do we learn that The Man in Black is the Dread Pirate Roberts, who is actually Wesley and Roberts is a Legacy Character. In the end Wesley suggests that Inigo become the new Roberts. Roberts ship is called the Revenge and there is indeed a lot of money in there.
- Wesley and Inigo are very well matched, both being master swordsmen. However, Inigo is using the sword his father crafted for Count Rugen, the six fingered man. The weight and balance would be slightly different than would be ideal for someone with the standard complement of five fingers. Wesley won the sword fight because Inigo was fighting with a disadvantage the whole time.
- Humperdink's whole plot is to kill Buttercup and frame Gilder for it to start a war. With the abduction of his wife by mysterious agents, he can still use this as an easy substitute. While Buttercup escapes with her life, Humperdink will presumably still sink two nations into war.
- Humperdink's free to live a long life with his cowardice...and try his plan again on another unsuspecting girl. And this time, he'll make sure to pick someone who has no True Love who could thwart him.