This chapter is significant because it places all of the main characters back in an order that does not fulfill their purpose in the story. In the past chapter, we made progress: Buttercup and Westley were reunited, Humperdinck was hunting for Buttercup but still able to show off his abilities, Inigo and Fezzik were doing what they did best when they fell, but did not die, at the hand of Westley. In the plot scheme, all was well until the end of the chapter when Buttercup allowed herself to return to Humperdinck, defying love. This chapter opens with the lovers separate, and everything else is in disarray. Inigo returns to drinking, having lost Vizzini and therefore a planner. Fezzik hides in a cave, having lost his life's crucial elements: Vizzini's planning and Inigo's friendship. In this chapter, the underbelly of this fairy tale is revealed: we see all the characters at their worst, their tragic flaws subverting all else.

Since the characters have all hit rock bottom, the trajectory changes direction and the characters realize what they must do individually to remedy their lives. Buttercup must find Westley. Fezzik and Inigo must find Westley. Westley, for his part, must simply stay alive long enough to be found. This chapter is a turning point in the story. Until now, Humperdinck was ridiculous and arrogant, but rarely evil. As he finds himself losing power to the dying Westley, his evil side emerges and we realize that he is the ultimate person to defeat, the force between Westley and everybody else, the obstacle everyone must overcome. Humperdinck begins plotting for Buttercup's murder, and he loses his patience and kills Westley. Good plots itself against evil quite unambiguously in this chapter. Although this chapter skips quickly from Westley to Buttercup to Inigo to Fezzik and then back again, these characters become united in their missions, all of which require breaking up the wedding.

Finally, this is the chapter where bad things happen, death enters and William Goldman, as a child listening to this story, grows up. His interjection as he explains his coming into the knowledge that life is not fair, is easily the most poignant in the text, carrying none of the lightness or randomness of his other explanations. Westley dies here, and we know that death cannot be reversed.