So staranise has a fabulous take on how to fix the princess bride which corresponded to a lot of my frustrations on Buttercups writing; though I tended to approach it from the other way round. I posted a short version of this in the comments on that post and went back and reread it this morning. Said, no wait I can do better, which is what I hope this post is.
I was always so frustrated with how flat Buttercup was but I approached it from the other way round. The Princess Bride is a pastiche of fairy tales, so my thought experiments in it have always leaned towards what if Buttercup was genre savvy? The world she lives in runs on fairy tale logic and Buttercup has always been good at identifying the stories she’s surrounding her.
We could have examples of that- Buttercup refusing to go to the well on Wednesday because that’s when the old woman from the woods (a Good Neighbor) comes out and sits by it and Buttercup doesn’t have it in her to be polite to her. A boy from two farms over offers her the beans he got trading away the families last cow and she tells him to go home and plant them instead. A frog asks her for a kiss and she sends him over to poorest family in town, whose daughters are notably kind; next thing anybody knows they been whisked away by a prince in disguise whose fallen madly in love with the youngest. All of those would establish Buttercup as both competent, clever, and (relatively) kind.
When she was young, Buttercup thought she knew what story she was living in. She and Wesley had True Love and he would go off and have adventures and come home wealthy and rescue her in some way and then they would live Happily Ever After. And then she gets the news and she realizes must have been wrong. Buttercup doesn't know what story she's living in, but she knows now it’s not a happy one.
She emerges from her year of mourning the Most Beautiful Woman in the World and flattened by grief, chronically depressed, knowing that she will never love again. So when Prince Humperdinck rides up to her and orders her to marry him she says, "I will marry the man that brings me the head and the heart of the Dread Pirate Roberts and no other." Because being the Most Beautiful Woman in the World means she can say things like that and people will listen. Beautiful women handing out impossible quests for their hand is a staple of fairytales. She can act within the constraints of her role.
Prince Humperdinck does not say, “as you wish,” but something about the way he nods his head in acquiescence drives her back inside for a week.
Word of her proclamation spreads and wealthy men flock to her. They gift her with jewels and silk, dance attendance on her, brag of the ships they have hired to hunt down her pirate. She eats little and smiles less but the more men look upon her the further her challenge spreads. Buttercup becomes a wealthy woman on their gifts and that spreads her legend even further. The Most Beautiful Woman in the World has a certain amount of reach but a wealthy beautiful woman has even more.
And Buttercup is willing to use every inch of it. Grief makes her cold, and she knows what happens to women who don't marry their True Loves in this world. They are not the heroes of anyone's story.
The Dread Pirate Roberts, on his new ship, notices an increase in people refusing to surrender. Eventually he starts asking why.
The first man, a sailor in the prime of his life, tells him about a beautiful women and they say, you murdered her brother and she cannot eat or sleep while you still walk the earth.
The second, a noble, greedy and grasping. What’s does it matter, he says, she wants your head and your heart and will marry the man who brings it to her.
The third, a midshipman with stars in his eyes says, they say you murdered her One True Love and she’s sworn to never love again but she’ll marry the man who kills you.
We can still have the kidnap plot, one of her suitors getting impatient maybe? Hell, it can even be the six fingered man so we can still get get Inigo Montoya and I want my father back. But this time when Roberts catches up to her, he says "I have brought you the head and the heart of the Dread Pirate Roberts. I believe you've made promises to that effect."
Buttercup doesn’t try to push him off a cliff, she tries to stab him. Then he reveals himself and it turns out Buttercup was right about the kind of story she was living in originally. It just took them more pain than was necessary to get there.
They don’t need to go on the run (unless they want to) because Wesley filled the terms of her challenge. They can retire on her money and live Happily Ever After.