Chapter One, "The Bride," begins by explaining that the year Buttercup was born, the most beautiful woman in the world was a French scullery maid who had a weakness for chocolate and soon lost her beautiful figure to chocolate mints and nougat. The chapter proceeds to chronicle Buttercup's early years through a timeline of the world's most beautiful women and their humorous and tragic downfalls, ultimately leaving Buttercup, age seventeen, barely in the top twenty.
But beauty did not matter to Buttercup, who spent her days riding her horse, avoiding her parents' arguments, avoiding any type of beauty routine, such as bathing, and hair-combing. She also spent her days taunting Westley, the young man who worked on her parents' land and answered to the name, "Farm Boy." The village boys all developed infatuations with the tomboyish Buttercup, but she had no use for them. Slowly, news of her beauty—or potential for beauty—spread across the kingdom, and one day Count Rugen, Prince Humperdinck's right-hand man, drops by their farm with his wife, the Countess, and an entire royal entourage. They come armed with an excuse that they must learn the secret to their cattle-raising, which is obviously untrue since Buttercup's parents are widely known to have some of the worst cows in the land. While Westley shows the Countess how to feed the cows, Buttercup feels a sudden intense jealousy of the Countess, who is the whole time ogling Westley. Buttercup is so swept by her own sentiments that she does not notice that the whole time, the Count is ogling her.
Buttercup is unable to sleep that night, and as she tosses and turns, she tries to pinpoint what the beautiful, rich Countess could have possibly desired in Westley. Soon before dawn, her jealousy (rated by the narrator, or rather, by "S. Morgenstern," as the fourth worst case of jealousy in history) overwhelms her. She knocks on Westley's door and confesses her love to him. She speaks long and beautifully, and when she finishes he slams the door in her face. She is horrified. She returns home, and spends the rest of the night rationalizing why he would not done such a thing. Buttercup concludes that he must be too dumb to respond, and that the best he would have been able to muster would be, "Duhhhhhhh, tanks, Buttercup." She bursts into tears and weeps the day away.
In the evening, Westley comes to her door, packed and preparing to leave for America. An exchange follows in which a confused Buttercup informs him spitefully that the Countess will not love him for long, and certainly would not be happy living with him in America. A frustrated Westley finally interrupts and explains that he returns her love. They then share a most beautiful good-bye kiss, one that ranks higher than the five kisses that had previously ranked highest in history.
During the next few weeks, Buttercup begins to take meticulous care of her personal appearance, so that when Westley returns he would still find her beautiful. She is gloriously happy, in love, and all of a sudden she is bombarded with the news that Westley was captured and killed by pirates. She retires to her room without hysteria, and when she at last emerges, thinner, wiser, sadder, she finally is the most beautiful woman in the world.
From the very beginning of the story, the narrator's tongue-in-cheek humor assures us that The Princess Bride is not an ordinary tale of heroism and fantasy. The main character, Buttercup, is not even the most beautiful woman in the world, as one might expect a fantastical heroine to be. The openly stated fact that she is barely in the top twenty makes the story even more surprising and humorous. Through added details of rankings, the narrative voice places a sincere mockery over the story and characters. We learn that the events of the first chapter take place after Paris, blue-jeans, taste, arguments, stew, and mirrors, but before Europe and ulcers. We watch Buttercup inadvertently scale the ranks of the world's most beautiful women. We realize that nothing in this tale is going to be smooth or conventional.