William Goldman begins this chapter with a cut, explaining that S. Morgenstern carries on about wedding festivities and tradition and other things of little interest, and then he tunes us into the present situations of his main characters. First he plops us back on the Cliffs on Insanity, where Inigo is regaining consciousness. He picks himself up, speculates upon his victor, and realizes that he must "go back to the beginning," meaning the Thieves Quarter, a dangerous, mean place. These were the instructions Vizzini had told him to do in case they were separated. William Goldman then interjects again to say that he omitted an overdone speech by Inigo about the fleeting nature of glory, and from here he segues from the subject into a sudden discussion of Robert Browning's inability to sell a single book of his first poetry collection.

When our narrator returns to the story, Inigo is in the Thieves Quarter, drinking himself into a happy stupor and waiting for Vizzini. The narrative switches to Fezzik, who is also waking up and wondering what to do next. He stumbles upon Vizzini's corpse and worries immensely that Inigo has also been killed. Finally, the sad and confused giant stops to rest in a cave, where a group of boys taunt him as he quietly comforts himself with rhymes. Then we switch to Westley, who is in the Zoo of Death, having his wounds nursed by a silent nodding albino, and learning through a tedious questioning of his caretaker that he was to be tortured to death. He resolves not to be broken. Last, we switch to Buttercup, who fears sincerely that all the chaos of the wedding festivities will break her entirely. The countdown to the wedding begins. The king dies and Buttercup is made Florin's queen, only to be booed by a crone in the crowd for leaving her true love, Westley, behind. Immediately afterward, we are informed that this was the first of many nightmares, and William Goldman interjects again to talk about the impressiveness of that fake- out, and how deeply it had upset him as a child. Here Goldman speaks of how perturbed he felt at the idea that Buttercup could ever have married Humperdinck, and not until an old neighbor of his explains that life is not fair did William finally understand why the dream had upset him so badly. He then warns us again that life is not fair, and that The Princess Bride is not necessarily fair either: "This isn't Curious George Uses the Potty," he explains at last.

The narrative returns to Buttercup. She has many more nightmares, mostly of her children calling her a murderer and then dying in her arms. Finally she tells Humperdinck that she still loves Westley and must find and marry him. Humperdinck is surprisingly calm about this and suggests that she write a message that his four fastest ships can carry in each direction in an attempt to track down Westley's pirate ship, Revenge. Humperdinck then thinks privately that he must demonstrate to his kingdom how deeply he loves Buttercup, so that when he strangles her on their wedding night, nobody will think twice about blaming Guilder, and everybody will want to go to war, thus activating his plan.

The next few weeks rush by quickly: Count Rugen begins his torture experiments on Westley, who takes his mind away and thinks of Buttercup, therefore feeling no pain. Buttercup waits impatiently for Westley's reply, all the while speaking joyfully of Westley to Humperdinck. This joyful talking irritates Humperdinck who is beginning to feel threatened, so he completes the circle by instructing Count Rugen to torture Westley further. To embellish the façade that he the Guilderians are plotting against Buttercup, Humperdinck demands that Yellin empty the Thieves Quarters, where the assassins may be hiding. Yellin is confused by this, but forms a brute squad and sets to work. At the end of this conversation, Humperdinck and Yellin hear a horrendous scream, which turns out to be a wild dog that Count Rugen has put to death on his "Machine," the contraption he then uses to torture Westley. Westley, surprisingly, is still doing fine. Count Rugen explains quite companionably to him about the machine and his study on suffering, and when he finally tries Westley on the machine at a very low level, Westley weeps in anguish, no longer remove himself from pain through thoughts of Buttercup.

Yellin is having somewhat of a difficult time emptying the Thieves Quarters, especially because a drunk Spaniard is threatening the brute squad with his sword. This of course is Inigo, and soon Fezzik arrives on the scene, bops the brutes on the head and nurses the sick, raving Inigo back to health, all the while informing him of the events of the past weeks. Inigo devises a plan to find the man in black (Westley) and ask him to create a mighty plan so that he can find the six-fingered man (Count Rugen), thus avenging his father's death and saving the man in black from whatever death Humperdinck has devised for him.

Meanwhile, Buttercup mentions to Humperdinck about the four letter-carrying ships and realizes that he was lying when he said that he sent them. She then calls him cowardly, a weakling, and he is infuriated. He throws her into her room, and marches off to the Zoo of Death and sets Westley on the machine at the highest setting, thus killing him. Right before this moment, William Goldman interrupts again, explaining how first he wept and then his heart hardened when his father told him that Westley was killed. Inigo and Fezzik—and everybody in Florin City—can hear Westley's death scream. Inigo immediately recognizes it as the sound of ultimate suffering, as it was the sound his heart made when his father was killed. The two friends push through the crowd, find an entrance to the Zoo of Death with some help from the albino, and approach it.