It’s a classic story and a cult favourite. “As You Wish” has become immortalised as the purest form of love. Spoken at weddings and stitched into anniversary gifts. And yes, Westley is handsome, charismatic and totally swoon-worthy. But, if we strip away the Mills & Boons, is he still the dream man? Surely, it’s… inconceivable?
Lets be clear; I’m a huge Princess Bride fan — always have been. My sisters and I grew up quoting nearly the entire script, dreaming of being Buttercup, and falling in love with Cary Elwes. Watching it again as an adult, I still feel the magic. I still cry remembering that Peter Falk has passed away. I still get goosebumps at “Drop. Your. Sword.
But through older (and maybe slightly more jaded) eyes, I’ve started to wonder… was Westley really the perfect romantic hero I thought he was?
Was “As you wish” a tender declaration of love from a shy, loyal farm boy — or was it the love-bombing phase of a floppy-haired narcissist in a poet shirt?
Let’s discuss the Princess Bride pirate portrayer.
He’s Alive?!
Let’s starts with the basics. Westley leaves.
Sure, he tells Buttercup he’ll return after seeking his fortune. But what does he actually do? He disappears without a single letter, message, or pigeon. She’s left with nothing but a vague promise and a sunset silhouette — and then years pass. She’s eventually told he was killed by the Dread Pirate Roberts. So… she mourns. She grieves. She declares she will “never love again”.
And then, surprise! He is alive. He has been alive this whole time. Without a word, a letter, a a visit home. And then, he comes back. Not with a heartfelt explanation or an apology. No, he returns in disguise, lurking in the shadows like a slightly condescending Batman, and immediately starts judging her for not waiting forever for a dead man.
From the start, there’s a strange sense of entitlement woven through Westley’s idea of love. His absence and silence was never explained, and yet he expects loyalty without contact, faith without reassurance. Is that romantic? Or is that emotional manipulation?
The Loyalty Test (and the Raised Hand)
When Westley finally bothers to return it isn’t a romantic reunion, it’s a test.
Buttercup doesn’t recognise him in his “Dread Pirate Roberts” disguise (understandably — the man has a mask and perfect lighting). So naturally, she tries to defend herself and make him nervous by saying that the Prince will find her. She isn’t declaring love, just stating facts.
Now, let’s remember that Westley lived in this kingdom for a good chunk of his life, chances are he could be well aware that the Prince could choose his bride. Without any consent needed. But, of course, our farm boy immediately jumps to the conclusion that Buttercup has betrayed him and is now marrying another out of love.
He is pissed. He snaps.
He accuses her of betrayal, lashes out with cold sarcasm, and even raises a hand to strike her. It’s such a quick moment in the film and barely discussed but…. he threatened to hit her.
Moments later, when he does reveal who he is, he doesn’t offer comfort. He doesn’t apologise. Instead, he asks why she didn’t wait for him. My man… you were dead? (Except he wasn’t, was he. He was just sailing around waiting for the perfect hero moment to return).
He then utters, “Death cannot stop true love. It can only delay it for a while“. Sounds beautiful, right? But now that we’ve all been to therapy… it kind of feels like love bombing with a poetic twist. His love, in this moment, isn’t something tender — it’s a weapon. One he uses to guilt her, shame her, and test her worthiness. And she failed. Hard.
The Dread Pirate Persona
Let’s talk about the whole Dread Pirate Roberts situation, because it’s easy to forget what that title actually means. We get caught up in the charm, the dramatic swordplay, the black mask — but Westley didn’t just adopt a mysterious identity. He became the literal embodiment of a man feared across the seas.
The Dread Pirate Roberts is known for pillaging, kidnapping, and killing without mercy. Buttercup believes Westley died at his hands because, historically, the Dread Pirate doesn’t leave survivors. That’s his whole brand.
And Westley… just steps into those shoes. He admits he kept the title, the outfit, the name — and, presumably, the reputation. He doesn’t deny doing some morally questionable stuff. In fact, he implies he got pretty comfortable with the whole terrifying pirate gig.
Westley didn’t just go get rich or build a career. He chose to lean into the myth of a murderer, and then used it to manipulate everyone around him — including Buttercup. And we are supposed to see him as a romantic hero?
At some point, we have to ask: Did he come back as a devoted lover, or as a man who liked being feared just a little too much?
He Treats Fezzik and Inigo Like Dirt (After They Save His Life)
Let’s not forget: Westley is literally dead-adjacent when Fezzik and Inigo find him.
They don’t have to help him. Inigo, bless his sword-wielding heart, believes Westley is the only one who can help him take down Count Rugen. So what does he do? He drags him to Miracle Max, barters for a cure, and brings him back from being mostly dead.
Fezzik then carries Westley’s unconscious body on his back, helps sneak him into the castle, and even props him up during the final confrontation.
So how does our charming hero respond?
He’s snarky, impatient, and rude.
While these two giant cinnamon rolls are risking their lives to help him and Buttercup, Westley snaps at them about their plan, why they didn’t tell him about a wheelbarrow they didn’t know he would want to use and is sarcastic and ungrateful when Fezzik is excited about him literally coming. back. to. life!
For a man who claims to believe in true love, Westley sure doesn’t show much love to the people keeping him alive.
Love, Storytelling, and the Mask
Here’s the thing: The Princess Bride is a masterpiece. It’s satire and fairytale, comedy and comfort. It’s wrapped in childhood memories and framed by a grandfather’s voice. It taught us about love, loyalty, and standing up to six-fingered men.
But it also taught us to idolise a very flawed man.
Westley is charming. Clever. Romantic in all the ways young hearts want a storybook hero to be. But once you peel back the swashbuckling and poetic lines, what’s underneath isn’t always so golden.
He disappears without a word. He punishes Buttercup for grieving him. He treats his allies like background characters. He hides behind a mask — literally and emotionally. And yet we root for him, because we were told to. The Grandson tells us that Buttercup has to marry him “after all Westley did for her”. Buttercup’s dream tells us that she gave up her true love and she is therefore a queen of filth.
That’s the magic — and the danger — of storytelling.
We’re trained to love the man in the mask without ever asking what he’s hiding.
So was Westley the villain all along?
Maybe not, after all Humperdinck is literally planning to murder Buttercup to start a war. Maybe Westley was just a flawed man with a good heart and a flair for drama. Or maybe he was the Dread Pirate Gaslighter — all charm and cheekbones, wielding love like a sword.
Either way, the next time you hear “As you wish“, ask yourself — is it a promise, or a warning?
Is Westley still your dream guy? Let me know in the comments!
P.S. If you love dashing rogues, biting wit, and a sprinkle of “as you wish,” then you need to check out my Princess Bride FAQ.
It’s packed with behind-the-scenes facts, quotes, and hidden gems — because true love deserves a deep dive.
Read The Princess Bride FAQ here →
(Inconceivably good reading awaits.)
NB: This article is based solely on the Westley portrayed in the 1987 film.
