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  • Why didn't Westley contact Buttercup sooner?
    • Westley was gone five years, but while in the Fire Swamp he explains that he was only held prisoner for three years before becoming 'Dread Pirate Roberts'. That means that at any time he could have headed back to the farm (or even sent a message) and TOLD Buttercup that he was still alive. Instead he just hangs around playing with swords and puts his 'true love' through TWO YEARS of unnecessary grief and pain. And then he has the gall to be angry at her for being 'unfaithful"!
    • He doesn't become the Dread Pirate Roberts after three years. It's just that after three years the previous Roberts stops saying that he'll most likely kill Westley in the morning. Still, he COULD have sent a message any time in those five years, considering that he wasn't actually a prisoner - he was Roberts' valet.
    • That would drum up questions about how Westley escaped the Dread Pirate Roberts — or if the Dread Pirate Roberts spared him, which is impossible because, of course, the Dread Pirate Roberts leaves no survivors...
    • Also, Westley likely wanted to build up a nest egg, so that he could give Buttercup a better life than living on a farm when he returned.
    • Couldn't he have done that and let her know he was alive? If he'd sent a message saying "I'm still alive, but am working to provide your future" (his original plan), she would have happily waited it out and refused to marry the Prince. It's irritating he didn't make some attempt to reassure her.
    • It may not have been easy to do that and still maintain his cover.
    • Simplest explanation: being the massive, utter, and hopeless romantic that he is, Westley simply assumed that Buttercup would think "Oh, he's alive, and he'll be making his way back to me any time." He pretty much says as much after he asks her why she didn't wait, he just takes it as a given that she'd assume even death wouldn't stop him from coming back to her. So most likely he just got about the business of surviving and learning to be a Dread Pirate and figured once he'd found a suitable replacement he'd head back to Buttercup (who would be totally unsurprised to see him alive, to his thinking) and they'd live the rest of their lives comfortably on his retirement fund. Remember he was going across the sea to seek work anyway, and thus likely planned on being gone for several years in any event... being an oddly practical fellow, he just thought he'd found employment in an unexpected place and was going about the original plan.
    • If Westley told Buttercup that he was still alive, she'd have refused to marry the Prince and been killed for it. This way, as stated above, he could go about his original plan and once he'd earned his fortune come back and rescue her from her engagement (because, naturally, that would be no problem since they had the power of true love).
    • To be fair to Westley, it's not as if he could have just sent an email to Buttercup or texted her immediately with the information or even sent her a telegram. We're really understating just how bad mass-communication was in these days; the story is set in an age where communication over long distances was, at best, unreliable. There wasn't even really much of a postal service of which to speak, let alone international mail. Your best chance at communication over the ocean in those days was to basically give a letter to a sailor going vaguely in the direction you wanted the letter to go to and hope his ship didn't sink or that he didn't give it to the wrong person who just happened to have the same name or didn't leave it in a brothel on the other side of the world from where you wanted it to go or get drunk and lose it or accidentally drop it overboard or set it on fire or any number of ways it could have gotten lost somehow. Heck, even if it did get to her, it might have taken years to get to her anyway, by which time he'd probably be back in her life again anyway. In short, for all we know, he did send a message to her — it just got lost.
    • Added to that, Westley's letter couldn't have included that he survived an encounter with the Dread Pirate Roberts, because that would ruin the reputation. So it would have to omit the encounter entirely, in which case even if it did get to Buttercup before Westley returned, she'd most likely take it as having come from before the attack.
    • He might not have been being threatened with death after three years, but he was under Roberts power, and Roberts would never allow a message saying, "Hey, I've been a prisoner of the Dread Pirate Roberts, but don't worry, he let me live." He was still a prisoner, really, until Roberts offered to make him a pirate king.
    • Alternatively, he may not have known she knew of the attack. As mentioned above, news were slow. It is entirely possible that he assumed Buttercup thought he was still making his fortune somewhere, and so he continued his life as the pirate's valet. It is possible he didn't find out about the whole marriage ordeal until he arrived to Florin.
    • OR, being the hopeless romantic that he is, he did it out of love and then heartbreak. Initially, if the Dread Pirate Roberts was threatening him with death daily, what use would it be to tell his love he was alive if he might die any day? Why give her false hope? By the time he was not threatened anymore and handed the title, he may have received the news of Buttercup's engagement (in the book, she spent three years at princess lessons, so it's possible) and convinced himself that, since she was going to marry someone else, she clearly was not waiting for him anymore, so it was no use to communicate with her and he might as well let her be happy with Prince Humperdink. He only went after her when she was kidnapped because, obviously, being kidnapped is not how you spend a happy life and he didn't want her prisoner or dead.

    Death Scream 

  • The reason Westley, Inigo, and Fezzick team up at the end is because Inigo hears Westley's death scream, assumes it's because Westley is heartbroken over his true love marrying another, realizes they share the common goal of stopping Humperdink, and decides to find Westley and team up. But... how does Inigo know that Westley is Buttercup's true love? Inigo never found out the "Man in Black's" identity, and even if he had, how would he know that Westley loved Buttercup? Humperdink did everything in his power to hush it up by sending Westley to the pit of despair, and who would Buttercup have told? How would Inigo ever make that connection?
    • "The man in black was after the woman we captured... the prince, who I hate anyway, is marrying the woman we captured... someone is screaming so loudly I can hear it from here... It must be that the man in black is heartbroken that his love is marrying the prince! We can use this to our advantage!" This is the sort of conclusion he jumps to all the time. Remember, Westley was screaming because he was hooked up to a machine that was so painful it took off fifty years of his life in one go. It's coincidence that Inigo happened to be right about the man in black's relation to Buttercup. People tend to know things they shouldn't all the time in this movie.
    • The book does a somewhat better job of explaining it, but the above line of thought is pretty much what happens, with Fezzik bringing Inigo up to speed being played out over several pages and Inigo, being smarter than Fezzik, putting together the connection between the story told to the public regarding Princess Buttercup being kidnapped by pirates working for Guilder (Prince Humperdink allowing this much to be said publicaly as a smokescreen to obscure the fact that Westley is his captive) and The Sicilian Trio being hired to kidnap Buttercup.
    • In fact, the book doesn't mention True Love at all during these scenes! Inigo logically guesses that Humperdink - being the total bastard he is and having just had his plans to have his fiance murdered and Guilder framed for it foiled - would keep the Man in Black (he who did the foiling) as a captive for torture, rather than being turned loose as the rumors claim. Inigo further reasons that if he and Fezzik can rescue him, he will be in a better position to bargain for The Man In Black's aid in coming up with a plan to go after Count Rugen. Inigo's recognizing the Sound of Ultimate Suffering and equating that to The Man In Black is due to his reasoning that "who else would have cause for suffering on this festival day?"
    • It also helps that the Theory of Narrative Causality runs this universe.
    • Also, there's that Fezzik apparently filled him in while he was nursing Inigo back to health...though that leaves the question of just how Fezzik knows about it.
    • Fezzik worked for the brute squad, so it's possible he saw the Count and guessed that he was the six-fingered man (Inigo was Fezzik's friend and made his quest no secret, so even the giant would probably remember that much).
    • As best as I can figure out, Buttercup told everyone in the castle about the four letters, including the members of the Brute Squad, who told Fezzik.
    • It's pretty simple... Inigo took Bat Deduction training alongside his Master Swordsman stuff. That and Willing Suspension of Disbelief is probably expected.
    • Just for clarification: Inigo had already decided to team up with the Man in Black, reasoning that if the Man in Black outfenced Inigo and outfought Fezik, then he must have outsmarted Vizzini, "and a man who can do that can plan my castle onslaught any day." The scream just let them track down where the Man in Black was. The reasoning that "the Man in Black was after Princess Buttercup, who's set to marry Prince Humperdinck today, as we hear the Sound of Ultimate Suffering, must mean the Man in Black loves Princess Buttercup and is Suffering because she's going to marry another man in a few hours" is about as sound as "because he bested our best swordfighter with steel and our best fistfighter with strength he must have outsmarted our smartest, and thus can pull a plan to let three guys successfully storm an entire castle out of his ass."

    Dread Pirate and surrender 

  • According to the story, the Dread Pirate Roberts would always kill his captives. Westley explains that it's to prevent people from disobeying him. In reality, wouldn't killing everybody you captured just give your targets an incentive to always fight to the death? Historically, pirates would usually just kill people who resisted, to give them a reason to surrender without a fight.
    • Westley says that Roberts was intrigued by Westley's lack of begging, which is why he didn't kill him. Maybe Roberts would threaten to kill people just to find out if they had any dignity— and was disappointed by everyone except for Westley.
    • This had to be an exaggeration. If the Dread Pirate Roberts and his crew actually killed everyone on the ships they captured, then there would be no one to tell tales about the Dread Pirate Roberts. Either not all captives are killed or some people are allowed to get away. Westley lies about other things; so why take his word on this?
    • This has bothered me for a long time. Another problem with it is this: If Roberts takes no prisoners, your only hope is to fight back as hard as possible on the chance you would win, rather than handing over your stuff in terror without a fight. The only reason for Roberts to take no prisoners is that it makes the character sound really scary and terrible to the reader.
    • If you think about the whole point of the Dread Pirate Roberts turns this Fridge Logic into Fridge Brilliance.
    • You could probably get away with the whole thing without killing anyone. Say at the beginning, a heavily ladden ship doesn't make port. Happens all the time. The first Roberts starts a rumor in one port about a pirate who kills everyone and takes their treasure. If anyone asks how a no-survivor pirate is known about, Roberts would just say that one person survived long enough to tell his rescuers before dying of his injuries. The rumor spreads and anytime a ship doesn't make it in for whatever reason (sunk, lost in storm, lost in direction, mutiny, other pirates, etc.), Roberts is blamed. Roberts builds up a crew under the Dread Pirate Roberts name. Anytime Roberts comes across a ship, Robert pretends to strike a rapport with someone on board. He offers them a deal: in exchange for their silence and all the stuff aboard, he'll make a small concession and let this crew live. He threatens to track down and kill anyone who speaks. No one risks his wrath, no one hears, no one dies, and Roberts makes an unliteral killing.
    • Remember, "Takes no prisoners" is not the same thing as "kills everyone." If you resist, you are not captured, you die. If you don't resist, you're just robbed blind. The problem is that not everyone makes this connection, so the reputation makes people think that it's either a kill or be killed situation, and therefore do resist, which leads to their deaths...and the vicious cycle.
    • If I'm remembering properly, the idea is that "Everyone knows that the Dread Pirate Roberts" takes no prisoners, which sets up the mythos around the man, and then the rest of Westley's story shows that the mythos simply isn't true.
    • In fact, it's quite likely that the first Dread Pirate Roberts spared a lot of people early on upon the condition of their going back and telling everyone about him, but instructing them to leave out that they survived an encounter with The Dread Pirate Roberts... or else. Turning himself into an urban legend would be easy enough a feat in those times.
    • Don't forget about Roberts' crew(s) themselves - the way pirates operate is that they go out, score a lot of loot, then immediately go to the nearest port and blow it all on booze and hookers (since pirates tend to die young, there's no sense saving it). The pirates could come into town with a big score, getting everyone attention by tossing money around, then brag that they're part of the Dread Pirate Roberts' crew and they just slaughtered a whole mess of traders, because their fearsome captain leaves no survivors. True or not, it'd get people talking.
    • The book explains this. It really is the "Surrender and don't fight back, you live" explanation, and pretty much everyone knows that. Most people specifically don't fight back because of Roberts' reputation, which is specifically why it's a legacy title. The original version of "No one would surrender to the Dread Pirate Westley" actually goes into detail, and explains that the first time Roberts let him try running a raid, the challenged ship called back "Who demands it?!" and he, flummoxed, calls back "Westley!" The defending crew then proceeds to fight back in a bloody and harsh battle. His mentor specifically says he did it this way to point out the value of the Dread Pirate Roberts moniker.
      • The book doesn't quite spell it out that clearly. It does say that people are afraid to fight because of the reputation, but it says nothing about what happens to people who don't fight. One possibility is in the definition of "captives".

        First, Roberts takes credit for ships lost at sea, claiming the crew died because they defied him. He then spreads rumors about how he kills all his captives. Next, he spreads more rumors, but these are about how you might live. He tells you to abandon your ship, or to give him all your valuable cargo. If you abandon ship, you were never a captive. If you accept an offer to simply give him all your goods, you were never a captive. If you fight, but then run, you are allowed to get to the boats and you were never a captive. If you throw your cargo overboard in order to lighten your load, it works, he collects the cargo and you were never a captive. If you fight and don't back down you likely die, and if nobody except his crew knows what happened to you then you are rumored to be taken as his "captive", and "everyone know the Dread Pirate Roberts never leaves captives alive." So long as there is a way for him to get the cargo and yet you were never his captive, you take it and he doesn't have to kill you. So long as everyone knows the way out, Roberts gets the cargo without killing everyone.

    Taking the six-fingered sword 

  • Just before Inigo duels the Man in Black, Inigo describes how the six-fingered man (who we later learn to be Count Rugen) commissioned a sword from his father, Domingo Montoya. When Rugen went to pick up the sword—one of the finest ever crafted—Rugen offered only one-tenth the previously agreed price. Domingo refused, and Rugen killed him. Why didn't Rugen take the sword after killing Domingo? How is it that Inigo now has the sword?
    • In the book, it says that Inigo's father gave back the deposit to the Count and verbally gave the sword to Inigo before he was killed. Inigo's screams brought twenty men from the village before Rugen could even touch the sword. Rugen claimed Domingo attacked him with the sword (even though the town knew it was a lie) meaning it wasn't his to begin with. The Montoyas had no money in the house so Rugen couldn't claim to have purchased it. Rugen would have had to kill twenty-one people plus the villagers who heard that fight if he wanted to leave with the sword. As he's leaving Inigo takes the sword and challenges/insults Rugen. Rugen wins and scars Inigo who then passes out. It's one thing to beat an opponent who has threatened and insulted you and quite another to pry a sword from the hands of an unconscious 10 year old orphan surrounded by people who know you're the one who made him an orphan.
    • It's relatively clear that Rugen didn't actually care about the sword itself at all, and only ordered the sword in order to deliberately waste Domingo's time making it only to insult and reject it. It's all part of his grand scheme to torture people in the most sublime and complete way he possibly can, which, as is common for a Princess Bride character, is the one and only thing he cares about.
    • You mean he didn't really want a sword to fit six fingers? That'd be a useful thing to have, wouldn't it?
    • Well, it's not like a set of brass knuckles, is it? Would it really be so hard to find a sword with a grip long enough for that one extra finger?
    • Actually, it's not the length of the grip that's the problem, a long grip is easy to make. The problem is making the longer grip that doesn't throw off the balance of the weapon. This is specifically addressed in the book and glossed over in the movie.
    • Of course, he might not actually fight with his six-fingered hand. Just because he has six fingers on one hand doesn't mean that hand is his main hand. It's just a distinguishing feature for Inigo to recognize Rugen.
    • Domingo, I know something you don't know—I * am* left handed.
    • ZING!!!
    • For reference, the book does specifically call it the Six-fingered Sword.
    • What, you've never seen someone point out all the flaws of something they're interested in buying? Rugen was just going to extremes because he was an ass. The book made it clear that Rugen was just trying to haggle with a poor craftsman by setting the price really low, and that since Domingo was a true artist he became enraged at Rugen treating his masterpiece as if it were a loaf of bread or something. Domingo even says, I believe, that he didn't care about the money and probably would have done the work for free if he'd just been asked (because it was challenging and interesting work), it was the attempt to haggle that enraged him.
    • Plus, Rugen had lots of both money and power, he may very well be able to have paid several blacksmiths and weapon-crafters to make him functional swords/knives/axes/whatever to fit his six fingers. However, Domingo Montoya was a true artist of the trade, so the sword he created would not only be functional but also pretty.
      • Not true. If memory serves, the book specifically calls out that Domingo has zero interest in making gilded and bejeweled swords for foppish nobles who just want a pretty belt ornament they have no intention of drawing in anger. His friend, the master blacksmith with the artisan reputation, handles that crap. This friend has the reputation as the master swordsmith, but when he gets a commission for an exceptional weapon he knows to be beyond his skills, then he gives it to Domingo. Rugen somehow learned that Domingo was the truly gifted swordsmith and approached him directly, not bothering to go through the friend with the reputation. Domingo took the job because of the difficulty and the opportunity to create a truly unique masterpiece. Neither Domingo nor Rugen were interested in the sword looking pretty, it being a blade that would function at the highest end of swordsmanship for a man with six fingers on his dueling hand was the important part.

    Buttercup's reaction to the Dread Pirate 

  • Am I the only one bothered by the fact Buttercup ISN'T bothered by the fact that Westley has apparently become a ruthless slaughtering murderer during his time as the latest Dread Pirate Roberts since she last saw him?
    • Once Westley reveals his true identity, she probably assumes that he didn't really do any of the things the DPR was reputed to have done, because she knows he's incapable of such things.
    • Inigo and Fezzik are also both professional murderers. It's a pretty grim book if you think about it, in that respect. The part that separates the good guys from the bad seems to be that the villains torture their victims first - like, a lot - or kill just for fun, as opposed to revenge or money.
    • Inigo makes a distinction between "revenge" and "justice". Part of it is that he insists he must defeat Count Rugen in a fair fight, rather than killing him just to kill him. Both Inigo and Fezzik are partially redeemed by the fact that they give Westley the dignity of fighting for his life in a fair match rather than just killing him.
    • She also isn't apparently bothered by all the vile things he said to her, the mocking, etc. before the reveal.
    • To be fair, this one can and is clearly explained by the fact that he thought the woman he was in love with and had gone through a lot of bother to find and see again was getting married to another man, and a rich asshole at that. He's a bit upset and bitter by this, hence saying the nasty things to her. Note how said nasty things stop being said when, upon talking about the day she found out the man she truly loved her was dead, she screams "I died that day!" at him and tries to push him off a cliff in rage at thinking he's the guy who killed him. After this, he's satisfied that she genuinely did and still does love him, while she's just overjoyed that he's alive and thus is willing to forgive a few mean things being said.
    • The idea of the Dread Pirate Robert's mantle is to be so ridiculously terrifying that no one would dare take up arms against you. In the movie, you see how they scare off the guards instead of kill them? That's what Westley did for the past few years.
    • No, you're not.
    • Arguably, he didn't kill anybody, any more than the previous Roberts did. He just coasted on the reputation.
    • That XKCD bugs me. The Spaniard is also a professional killer.
    • Does Buttercup know this? She knows he helped to kidnap her but Vizzini was the one talking about killing her and Inigo may have even said something while she was conscious about how he wasn't comfortable with the plan. Sure, his part in that plot wasn't good but it's not the mass murder Roberts is supposedly guilty of either.
    • He's a swordsman. Let's face it; a swordsman who acts as a mercenary, as Inigo clearly was, can be fairly safely assumed to have killed a few people in his day.
    • Not really. Maybe it is because I am a rather amoral person, but if someone dear to me whom I thought had died was revealed to be alive, the fact that they had killed a bunch of people I don't know or care about during that time period wouldn't bother me too much (except if they were on the run because of it or something, but that would be more of a practical concern than a moral issue).
    • ... Do you often introduce yourself as "a rather amoral person"?
    • By the time Westley takes over the mantle of Roberts the legend is so infamous that he doesn't have to kill anyone at all, simply run up his colors and any ship will simply send over their valuables without a fight. Although he does seem quite willing and able to kill when necessary (Vizzini) he doesn't seem to take any pleasure in it.
    • You're probably not, but frankly if Disney can make one of the most successful trilogies of movies ever by making pirates the heroes, let alone sticking some vague acts of piracy in a hero's past, you're probably better off not bringing it up unless you want to look like a fussy Moral Guardian.
    • Was it not already obvious that Buttercup's not exactly the sharpest tool in the shed?
    • Once Westley explained he only became the DPR five years ago and there were several men who passed the title on, she would have realized he never killed all the men Roberts was supposed to have—other men did that. The only time he could have been killing people was during those five years. She likely believed he killed as few as possible. Or she forgave them because she knew he had to do it as part of his cover, to keep the pirates from killing him, until he could make it back to her.
      • Technically, he was only the DPR for two years.
    • Without wanting to sound quite as Nietzschean as our 'amoral' friend up there, let's face it; to Buttercup, the people Westley may-or-may-not have killed (and while the Dread Pirate Roberts identity may have minimised the blood loss, let's be honest; you probably didn't spend any real amount of time as a pirate in those or any days without getting your hands a little bit dirty at least) are hypothetical people she's never met and has no real awareness of beyond the abstract, while Westley — the one true love of her life who she thought was dead, the thought of which completely broke her heart — is in her arms once again. While it might trouble her at times as the years go by, at that precise moment she probably didn't give a single solid fuck about anything other than Westley being alive and reunited with her once again. Morally and ethically questionable it may be, but hey — people are complicated. People fall in love with people who have killed all the time.
    • Deliberate Values Dissonance. Killing people doesn't seem to be that big a deal in this time/area. Buttercup is less mad at "Roberts" for being a pirate than she is that he's the pirate who killed her one true love. Westley was just out trying to make his fortune so he and Buttercup could marry, it's not his fault if some people were stupid enough try and fight the Dread Pirate Roberts.
      • I think we get a sense of when Wesley will or won't kill by the fact that he spares Inigo's life but kills Vizzini. He probably didn't have an intermediate option like diluting his poison on the spot so that Vizzini would have only been incapacitated, for one, and he also had the sense from conversing to Inigo throughout the sword fight that Inigo is a gun-for-hire whereas Vizzini is on a mission to do harm.
      • Clarifying the Deliberate Values Dissonance, historically, there’s a difference between what used to be called an assassin (someone who kills in cold blood, not just someone who targets famous people) and someone who kills someone else in a fight, even a fight the killer started. This troper recalls two stories by G. K. Chesterton in which someone killed someone else, a family member no less, with the protagonist reacting in horror — until it was explained that it was in a duel, which made it okay.
    • In the book, when he says, "Nobody would surrender to the Dread Pirate Westley," it's part of a story he's telling about how Roberts explained the reputation thing. Roberts challenges Westley that the next ship they go after, he should announce to them that they're being attacked by the Dread Pirate Westley; he does so, the other ship doesn't take him seriously, and it ends up being a bitter fight between the two ships. Roberts, however, can get a ship to give up its valuables without a fight. So, yes, Westley must have killed someone, at least in that particular fight (heck, he might have killed someone on Roberts' crew when he was first captured), but once he had and adopted the name properly, there was probably a minimum of bloodshed.

    Potted Plant 

  • Buttercup could be replaced with a small potted plant without materially affecting the story. Despite being the title character.
    • Oh, and what about Westley striking her?
    • Yep... We call that Eighties Heroine Syndrome where I'm from.
    • Honestly, I liked the fact that Westley struck her (or threatens so). It's a character flaw that humanizes him. She's annoying as all hell, and getting frustrated with her is entirely realistic even if it's not admirable. Plus, I hate the Knight in Shining Armor who Wouldn't Hit a Girl. If you'd smack an obnoxious male, then you should smack an obnoxious female. But that's just me, your mileage may vary.
    • At the time he was threatening to hit her, he was also pretending to be the Dread Pirate Roberts (which he was, actually, but you know what I mean), so I think the threat was just part of his act and he never actually intended to hit her. Of course, as stated, hitting a female should be no different from hitting a male, but I still think hitting one's Love Interest, regardless of gender, might be in bad form.
    • At that time he thought she actually broke her promise and ran off with Humperdinck as soon as he was out of the picture. He was heartbroken and felt betrayed and his Dread Pirate act is either his way of taking revenge or his way of testing her true loyalties. Granted, that's all pretty fucked up too if you think about it, but hey, people do crazy things when they think they've been dumped.
    • He also tells her "where I'm from..." That's either a subtle clue and a reminder that she should think "oh, right, we have rules like that where I'm from, as well... But is there the same rule for guys? Wait, why am I thinking about feminism when I've got Eighties Heroine Syndrome? Whatever, back to non-confrontational potted plant time," or it's all for his Dread Pirate Roberts act and he'd almost definitely never hit her anyway.
    • He threatens to hit her because she was 'lying' about him not having loved anyone as much as she did. The hell? Even if she was wrong about that, she wasn't lying. She just didn't know that he had loved anyone. Even if her love had been shallow, she had no reason to think that Roberts had ever loved anyone even that much. And when he's been supposedly dead for five years, it's kind of unreasonable to expect her to stay devoted to him. I mean, they weren't even married!
    • True Love supersedes things like marriage and death. That was sorta the point explained later. And the 'lying' part wasn't about whether Roberts had known love. It was about Buttercup's love. The slap (or threat of it) was his way of saying, "Oh, so you loved him soooooo much, then why the hell are you marrying another dude?''
    • In the book, he does in fact strike her. Actually, the exact line is: "He slapped her."
    • That would have to be one annoying potted plant to convince the Prince to kill Westley.
    • Very good point. Buttercup was useless and helpless most of the movie, but the way she stood up to Humperdinck was one of her best and most powerful scenes, even aside from the fact it compelled Humperdinck into rushing off and killing Westley.
    • She's supposed to be a satire of fairy tale girls, the kind that are pretty but naive and don't do much of anything.
    • Twilight. That is all.
    • ... ... Twilight was written decades after The Princess Bride was. What was ever the point of this bullet? That Stephanie Meyer unironically uses the exact same trope (female viewpoint character whose head is as empty as a flowerpot) that Goldman uses knowingly, ironically, and with much greater skill?
    • Technically the Prince would have trouble justifying war over Guilder soldiers killing a potted plant.
    • Westley striking Buttercup arguably falls under Deliberate Values Dissonance. The story is set at a time where standards about spousal abuse were a bit different than they are now. Not entirely admirable, perhaps, but there it is.

    You keep using that word 

  • "You keep using that word. I do not think it means what you think it means." Great line, often quoted to great effect. So what bugs me? The word "inconceivable" DOES mean what Vizzini thinks it means! It's not unusual to say "Unbelievable!" or "Incredible!" when something you're not expecting happens, so what's the problem here?
    • See, the thing is that Vizzini keeps using a word that means "so impossible as to be beyond serious consideration" to describe things that are happening or have already happened. Despite the fact that he is often using it figuratively to show his amazement, his companion Inigo chose to make believe he thought his boss was confused as to the word's definition, to make said boss the subject of fun.
    • I thought of that, and it doesn't work. Inigo has no sense of humor. But what Just Bugs Me isn't that bit itself, it's how people are always using the quote at face value, forgetting that Inigo is wrong (or joking, if you insist).
    • Inigo does have a sense of humor. He thinks it's funny to speak in rhyme with Fezzik, and to pretend to be left-handed. It's not much, but he does have a sense of humor.
    • Inigo isn't the one making the joke, per se. The author is. Inigo is genuinely puzzled that a man as smart as Vizzini would continue to so radically misjudge the improbability of things that are already happening or have already happened. He thinks Vizzini can't possibly be that stupid as to think all these bad events that keep happening to him are literally inconceivable when they just keep happening again and again, so he thinks Vizzini must have just misused the word, which Inigo understands because Inigo himself misuses words quite often. It's from the author's — and the audience's — perspective that Inigo's innocent attempt at a correction becomes a giant upraised middle finger to Vizzini's arrogance, overconfidence, and blind, denial-ridden tendency toward self-destruction. In that context — the original context — the line is, indeed, very funny. I will wholeheartedly agree with it being overquoted, though.
    • Wow — that is a really, really good answer. It all makes sense now.
    • I always thought that Vizzini used that word a bit too much like a swear. When Inigo said IDTIMWYTIM to him, I interpreted it as "you keep using that word like a swear ... and it's not."
    • This is the correct answer. Inigo is legitimately confused by Vizzini repeatedly using a word that isn't a curse as if it were. Inigo isn't quibbling about the exact definition of the word like a human dictionary. It's a simple joke about swearing.
    • It could be Inigo was interpreting Vizzini's use of the word as in the old joke with the translator who means to say his wife is barren, but accidentally says she is unbelievable. Vizinni using the word "inconceivable" as a word in itself, and Inigo puzzling it out from the root word, as English or Florentine may not be his original language.
    • Yet another possible explanation: Inigo is a great fencer, but he hasn't spent much (if any) time studying anything else since the age of ten or so. Maybe the word "inconceivable" doesn't mean what he thinks it means. But in his Book Dumb simplicity, he can still act as the author's device to mock Vizzini's arrogance.
    • Well keep in mind that Inigo says "I don't think it means what you think it does". He himself isn't sure that he's right about Vizzini being mistaken, he just suspects it.
    • Hi, i'm the bloke who wrote the first sarcastic response, and first of all, sorry for being a jerk. Guess I was having a bad day or something. However, I do stand by my answer. In the book, it's much more clear, as Inigo goes on a mini-rant, saying how no matter how many times Vizinni claims something to be inconceivable, it has happened, and therefore must be conceivable. So he does know what the word means and is making fun of Vizinni.
    • Maybe Inigo had just recently learned English. He has a strong accent, he occasionally uses odd words to convey his meaning, and he's unusually pedantic about correct usage (Let me 'splain...no, is too long, let me sum up) in a way that a native speaker wouldn't be. If he had just learned precisely what inconceivable means, he would be more bothered to hear a smart man like Vizzini using it to express his annoyance at something that, having happened, obviously was conceivable by someone, if not by Vizzini.
    • It makes perfect sense if Inigo was taking it literally; one learns the words and grammar to a language long before the colloquialism. Not to mention that turn of phrases differ from each other in countries that speak the same language (and in parts of the same country if they are sufficiently large enough).
    • I don't have a problem with taking what Inigo said at face value. "Inconceivable" is a much stronger word than "Incredible", a word used when something beggars the imagination, not simply because something happens you didn't expect. But Vizzini keeps using the word over and over again at events that are clearly not inconceivable, acting as if the word meant "Incredible". I've never heard anyone use the word the way Vizzini does, it is blatantly silly to be using the word that way, and Inigo calls him on it. Indeed, much humor comes from his more and more ridiculous uses of the word "Inconceivable" despite the fact that after you've seen your opponent do a certain number of impressive things, it really shouldn't be so inconceivable that he would do the next one.
    • I interpreted the line like this (going just by the movie here): The first time Vizzini uses "inconceivable" is appropriate, if slightly hyperbolic. Inigo says they might be followed, and Vizzini states that it's inconceivable that a search party would be prepared to chase them in the boat after the short amount of time that's passed. Then, when there IS a boat behind them, Vizzini says it's inconceivable that the boat could be after them. In this case, it isn't inconceivable, it's slightly improbable at best. Then, the next time he uses the word is when they're climbing the rope and Westley is climbing it faster than them. This isn't even improbable, it was 50/50 that he would climb faster than Fezzik. Finally, he uses the word when he cuts the rope and Westley grabs onto the cliff - a relatively simple action. Each of these four events is more probable and mundane than the last. Also, by this time (in my personal case, at least), his overuse of the word has become conspicuous, making Inigo's line even funnier.
    • Of course, the answer is actually right here. Inigo conceived of the notion that they might be followed. Therefore, by definition it is not inconceivable. But that's being especially harsh, so we move on a step: once it turns out they were being followed, after the initial suggestion they might be was dismissed as "inconceivable", there can be no argument. Vezzini is using the word incorrectly.
    • As an example of this, imagine you and your friend were walking up to a mountain. Your friend called the mountain "gargantuan". On your way up the mountain you saw one of its cliff faces. Your friend called it gargantuan. Then you guys walked past a boulder barely bigger than yourselves, which your friend called gargantuan. Sure, the word is somewhat appropriate for all these uses, but considering that he's choosing the most hyperbolic word available when there are more moderate synonyms available, it seems strange.
    • Not only that, but as he points out in the book: It was inconceivable for anyone to be following them. The Man in Black followed them anyway. It was inconceivable for him to climb the rope. He did it anyway. It was inconceivable that he could've grabbed on to the cliff...but he did anyway. So, obviously, it's not inconceivable.
  • As above, I always assumed that the repeated use of the word was the problem. Vizzini's first use of the word, while an example of him using five-dollar words because of his great (or imagined) intelligence, is not technically incorrect. Given the passae of time, it is in fact inconceivable that the Man in Black could have been an official search party. Buttercup would have had to fail to return on time, been missing long enough to arouse suspicion, had her trail searched to eliminate the possibility of an accident, and then a search party would have had to follow the trio's precise course as opposed to any other possible path of escape, all while they only needed to set sail in one direction and keep going. For someone from the castle to have done all of that and then caught up to them while they were only sailing across a channel...is indeed inconceivable. BUT, once it is clear that Westley is, in fact, following them, the entire paradigm of believability shifts in his favor. He's already established a new baseline, so his further exploits should have been downgraded to "impressive", or even "astonishing", but certainly no longer literally incapable of even being conceived of.

    Running away 

  • The height of Buttercup's absolute uselessness would have to be when she is kidnapped by Vizzini, Inigo and Fezzik. SHE'S SITTING ON A FREAKIN' HORSE! RIDE AWAY, YOU IDIOT!
    • She has all of about two seconds between realizing that Vizzini & company are trying to kidnap her and being knocked unconscious by Fezzik. Her thoughts probably ran along the lines of: "Oh my god, these guys are going to—" before falling asleep.
    • Also, her being an idiot is kind of the point.
    • Perhaps she simply just froze up in panic / fear? Considering that she's not an action hero, she's completely unused to being in dangerous situations and she's about to be kidnapped by three men, one of whom is a swordsman and the other of whom is a literal giant, I think calling Buttercup 'stupid' and 'useless' in this situation is a wee bit uncharitable. She might not have reacted particularly competently to events, but it's still an entirely natural human reaction to being in a high-stress situation and not knowing what to do. Some people fight, some people flee, some people freeze up. It happens.

    Jumping onto a horse 

  • I'm no doctor but wouldn't leaping from a huge ledge onto a horse be all sorts of bad news when you are stabbed a lot? Inigo was in bad shape after he did his thing and he was running amok just like he was fine. At that point, the adrenaline should be wearing off and the hysterical screaming from the agony should begin. Or at the very least, stumbling and fainting from holes and or blood loss.
    • His wounds reopened at the end of the book, making him fall from his horse.
    • Also, he probably didn't jump directly onto the horse. We can infer that Fezzik probably caught him and Westley as he did Buttercup.
    • I thought that too; it seemed very clear that both Westley and Inigo were caught by Fezzik (remember Westley was still recovering too and might not handle the landing well), and they only showed Buttercup for the "pretty damsel" and flowing wedding dress bit.

    Magic Sheet 
  • The 'Oh look, I have the magic sheet you need' bit bugs the crap out of me.
    • It's explained in the book. Sort of.
    • It's explained in the movie, too. Fezzik says that Miracle Max gave it to him. Plus, him pulling it out of nowhere is the joke.
    • It's a Holocaust cloak. Where did you get the magic sheet from?

    Iocane Powder 

  • Iocane powder is odorless, colorless, and tasteless. Yet a character picks up the vial, sniffs it, and declares, "Iocane powder."
    • Maybe it was the fact that he smelled nothing that tipped him off. It was clear that a man had been poisoned, and iocane powder could have been the most likely colorless, tasteless, odorless poison to be used.
    • It was. In the book, either the dialogue or the narrative said something about Humperdinck smelling "absolutely nothing" and then declaring it to be iocane powder.
    • Plus, the full line is, "Iocane powder; I'd bet my life on it." He doesn't actually say he identified it by smell, or even explain himself at all.
    • While the first explanation is quite plausible, I've always seen the line as a deliberate joke.
    • Fridge Logic: Why is iocaine powder so commonly known to be tasteless, yet it is "inconceivable" for a man using iocaine powder to have intentionally developed an immunity to it? If it kills in seconds, who would have been suspicious of food or drink that tasted perfectly normal? (Unless it was explained in the book, such as only Westley knowing it was tasteless, it's been too long since I've read it.)
    • You can figure it's tasteless by putting some on the tip of your tongue and not swallowing. Or just take a very small amount, maybe enough to make you ill but not enough to kill you.
    • My guess would be that it is known to be tasteless because people have been poisoned with it it food without detecting the difference in flavor as other poisons do.
    • Fridge Brilliance, maybe? If I recall correctly, Westley doesn't say anything about it being "commonly known" to be tasteless. He just says that it is. So the pertinent question for Vizzini to ask is "How does he know that it's tasteless?" Stupid Westley for giving Vizzini a clue, stupider Vizzini for not picking up on it.
    • The Prince was described as a master tracker, able to follow a falcon's trail on a cloudy day. His senses are so developed that he can smell the odorless.
    • Humperdinck knew all about Vizzini's plans and methods because he hired him. He knew in advance it was iocane, then pretended to identify it in order to look cool. You can even tell he's doing a "dramatic" voice.
    • Yes, but he always does a dramatic voice!
    • The iocane belonged to The Man in Black. He showed it to Vizzini, explained what it was and what it did. There's nothing in Vizzini's reaction to suggest that he was already familiar with iocane.
    • Vizzini is familiar with iocaine. He knows it comes from Australia. (And he also knows that you suspected he would be aware of the fact that you knew he knew it.)
    • He says he knew those things....
    • Well, Westley didn't correct him, so I think we should assume he knew where it came from unless there is a reason not to.
    • Still, the point is that it wasn't Vizzini's iocaine powder. The Man in Black was the one who brought it and used it, and even if he'd heard the name and knew it was from Australia, Vizzini clearly didn't know what it was at first.
    • Why would Westley acknowledge anything Vizzini says as true? He just sits there and lets Vizzini rant without interruption for a long time; it wouldn't serve any purpose to correct him, except to spoil the show. He's mostly finding Vizzini's verbal thrashing to be amusing.
    • Yes, but why would Vizzini have just made up that it was from Australia? It was Westley's iocane and there was every chance he knew where it was from. If he had said 'It's from America!' then Westley would have corrected him and he'd have appeared stupid. If Vizzini had not said anything about the origins, he would not have appeared stupid and randomly guessing had a very high probability of guessing wrong and then looking stupid. Vizzini may have read about iocane powder and so when it was identified he knew where it originated from at least.
    • The point is that even if Vizzini did know of iocaine and its origin (as revealed by Westley not contradicting him), that still wouldn't allow Humperdinck to have known of it via Vizzini, not unless he'd somehow mentioned it to the prince, or was in the habit of showing his prospective clients his records/library in which he had written down something about iocaine. However, assuming the line wasn't a joke, a great tracker and hunter like Humperdinck would surely know about many poisons, including that one.
    • Many poisons leave clues on the corpse. Possibly the prince thought, "Bloodshot eyes? Blue fingernails? His tongue turning black? A vial of probable poison with no smell? "Iocane powder. I'd bet my life on it."

    Vizzini's Gambit 

  • Why did Vizzini use a Poisoned Chalice Switcheroo? If he felt sure that the poison was in his goblet, he could have just taken the other one openly according to the rules of the game.
    • Because then he'd miss the opportunity to gloat while his opponent, convinced he won, suddenly felt the icy grip of death overtake him. Pity for him, The Man In Black wasn't playing by the rules he laid out.
    • Now hold on there. He never said only ONE cup was poisoned. Vizzini could at any time have refused to play the game; after all, he had the upper hand.
    • What upper hand? They were at an impasse. He may have had the princess, but he didn't have any way of getting away with her as long as the Man In Black was there.
    • Indeed. All Westley says is, "All right. Where is the poison? The battle of wits has begun. It ends when you decide and we both drink, and find out who is right... and who is dead." He never says only one cup is poisoned. Vizzini assumes that's the case.
    • The way I saw this scene was; they both cheated. The game was to discern where the poison is and choose the goblet that wouldn't kill you. DPR however is immune to the poison and poisoned both goblets. Vizzini's ploy was not to gloat but to see if DPR would hesitate to drink from "his" cup; if he didn't then the ploy worked, if he did then he had a plan b in store I'm sure. He is a Sicilian after all, and death is on the line.
    • Westley didn't cheat, Vizzini just assumed that one and only one goblet contained the poison; Westley stated nothing of the sort. If Vizzini had been a true genius instead of just Feigning Intelligence, he would have either determined that no one would enter a battle of wits when they had a 50% chance of losing simply from random chance, or he would have known that it's possible to develop an immunity to iocaine powder. Vizzini lost because he saw rules in the game that weren't there. I guess that actually makes him a Scrub.
    • Actually, if Vizzini had been a master of wits then he wouldn't have accepted anything offered to him by a known enemy, especially in such a tricksy situation.
    • Also, it wasn't a battle of wits based on random chance. The point, from Vizzini's perspective, was not to guess, but to figure it out based on logic. Which it kind of was, but the correct answer was "I'm not drinking either of these, you wanker."
      • But the point is, from Westley's point of view it appears to be a 50/50 chance, since he's put the decision of which goblet to drink in Vizzini's hands. And Vizzini should have been suspicious that the MIB would willingly give control of the game to him when death is on the line. Vizzini, for all his purported cleverness, doesn't think outside the box.
    • It's a battle of wits. Cheating is part of the game.
    • "Where is the poison? The battle of wits has begun." No mention of one and only one poisoned goblet.
    • I always thought he was guarding against cheating. If he chose correctly, the Man In Black could simply refuse to drink the poison, and jump across the table to kill him. He had to choose right while making his opponent think he had chosen wrong. Thus, Vizzini was a bit smarter than he appeared. Unfortunately he was gullible and arrogant, so he believed the MIB really fell for his transparent "look over there" ruse.
    • It's not established for certain that the Man in Black didn't fall for the "look over there" ruse. It just doesn't make any difference one way or another.
    • Watch the scene again. Vizzini waits for the MIB to sip first, then drinks happily. Vizzini thinks the MIB thinks he's drinking from the unpoisoned chalice, so Vizzini thinks he's drinking from the unpoisoned chalice. I supposed Vizzini would have refused to drink if the MIB had hesitated.
    • Westley didn't cheat. The quote was, "Where is the poison? The battle of wits has begun. It ends when you decide and we both drink, and find out who is right and who is dead." There was a correct answer: Vizzini could have chosen to drink from the bottle. But Vizzini failed the battle of wits, chose wrong, and died. Had he chosen right, both would have lived, and the battle would have continued.

    Battle of Wits instant victory 

  • On that subject: "We shall have a battle of wits. Let us say... To the death? Here, sniff this." Does anyone else think Westley should possibly have won right then, and then revealed the poison-both-goblets gambit as his main plan since it's unlikely (but possible) that anyone really would be that stupid or arrogant? It wouldn't have been very honorable at face value, but nor was the very specific wording he gave to allow the poison-both-goblets gambit (though the correct answer for Vizzini would be to drink from his own wine pouch if he had one, or the bottle if he could be sure it hadn't been tampered with, or even failing that a nearby stream—that way, there would be zero risk of choosing the poisoned goblet rather than 50/50, and would be perfectly within the rules set), and Vizzini had ordered Fezzik to ambush Westley and kill him with a rock. Anyway, it would have been using Vizzini's hubris against him slightly more directly, and provide for an interesting twist, though I don't know if it would have been better for the story (Vizzini being punished by the narrative for the stupidity of smelling something handed you by a person trying to kill you), worse (because it would have altered Westley's character even slightly in a way readers might like him less), or simply different (and not really comparable beyond personal preference, They Changed It, Now It Sucks! not being available to anyone without Ripple-Effect-Proof Memory).
    • There is an interesting piece of Fridge Brilliance in the iocane powder scene. In the book you have Vizzini ranting along the lines of "Because of X I can't take the goblet in front of me. Because of Y I can't take the goblet in front of you. But because of Z I can't take the goblet in front of me. But, because of N I can't take the goblet in front of you..." and so on. And at first you think it's all just for the joke, showing Vizzini talking out of his ass and actually not knowing what he was doing at all. But, in the book it also describes the MIB as getting more and more nervous and impatient and demanding Vizzini stop delaying and choose already. So why is the MIB nervous? Because if you follow Vizzini's circular logic to its ultimate conclusion, it leads to the conclusion that Vizzini should not drink from either cup! The MIB was getting nervous because he was worried that Vizzini was appearing to be gradually seeing through his trick! (And there would be risk of harm to Buttercup if Vizzini picked up on the trick).
    • Well, obviously the way to win Russian Roulette is to never pick up the gun... Maybe that scene as Westley playacting to toy with Vizzini, not exhibiting genuine nervousness.
    • Could be, but in the film, watch where he swallows from nervousness. It happens to be (could be coincidence) right when Vizzini is explaining that "you could have put the cup in front of you, relying on your strength to save you". He seems less nervous after Vizzini moves onto the next random arguments.
    • If anything, he's nervous because the longer he sits around wasting time with this guy, the less time he'll have to escape with Buttercup.
    • Yes exactly! I had that bit of Fridge Brilliance myself! Basically Vizzini kept coming up with reasons not to drink either goblet; he was merely trying to trip the MIB up into revealing which one he'd poisoned, but if he had kept going and followed his thoughts to their logical conclusion (or just known better than to drink anything his enemy gave him), he'd have realized he shouldn't drink from either goblet. Also note that aside from the nervous swallow, at the point where Vizzini starts talking about trusting in his strength to save him, the MIB clenches his fist. Vizzini was very close to the truth, albeit for the wrong reason, but his overconfidence and allowing his assumptions about the rules to overcome his logic were his undoing.
    • Note that in the book, there's a scene where Vizzini seems to be telepathically reading Buttercup's thoughts—though the implication is not that he's got psychic powers, but merely that he's exceptionally good at figuring out what people are thinking. During the Battle of Wits, he seems so confident in the choice he ultimately settles upon (he thinks the goblet in front of him is the one with the poison—until he switches them) that it's evident he read Westley's nervous behavior at a specific point as an indication that he "knew" Vizzini had determined the safe goblet was in front of Westley.

    Better Swordsman 

  • Why is Westley a better swordsman than Inigo, when Inigo has had 20 years of dedicated study while Westley had, at most, five years of learning from pirates?
    • Westley benefits from The Power of Love. He's almost unstoppable in large part because he's trying to save Buttercup. As said above, this is a fairy tale setting; that kind of thing is practically a genre convention.
    • It's explained slightly more in the book that Westley is only a superior swordsman when they're in an open area, but Inigo could take him if they were fighting around obstacles. Also, Westley's been fighting on pirate ships for the past few years while Inigo has been getting drunk in the gutter. He might be a little rusty.
    • The terrain was critical. It is stated outright that Inigo was superior in 2/3 possible terrains, but it just so happened that the lay of the battlefield allowed Westley to keep the fight within the one type of terrain where he was superior.
    • Wouldn't learning to fight on a pirate ship make it easier to fight around people and obstacles?
    • In the book, it's suggested that Inigo is undone by his overconfidence. As he is waiting for Westley to climb the cliff, before offering to help him up, he asks God to give him a true challenge and to make this Man in Black a master worthy of his skills. He then starts out fighting with his weak hand (the left one), thinking this will make the fight more fair. Inigo is thrown off-balance psychologically and begins to lose after he discovers that not only is The Man in Black a worthy opponent who can match him technique for technique but he also does the same hand-switching trick to challenge himself ("I'm not left-handed either.") In short, Inigo loses not because Westley is better but because of Hubris.
    • Inigo is using a sword perfectly crafted for a six fingered man. He has only the normal five. Fridge Brilliance.
    • Actually, he has mastered that sword.
    • It wouldn't matter the book makes it quite clear that in a fight between two sword wizards (masters) having a sword made to fit a different type of hand would be a crucial disadvantage. Westley is a mario, he is always second best at everything, but Inigo and Fezzik (Fezzik because he got used to fighting groups) are at a very slight disadvantage when they fight, meaning second best is good enough.
    • First, anyone who knows anything about fighting or any other human skill knows that there's no law of the universe stating that it's automatically impossible to beat someone with more training and experience than you. It's unlikely, but it does happen. Other factors influence the outcome of a fight, a whole shitload of them, including inherent skill; the fighters' current physical, mental, emotional, and spiritual conditions; luck; split second decisions and other matters of simple human fallibility; the particular combination of fighting styles between the fighters; the conditions of the environment, etc. Second, Inigo had just said that he's been spending more time in pursuit than in swordfighting studies.
    • I always thought it was because Inigo was just fighting for a job—Westley was fighting to save the life of the woman he loves.
    • The book actually makes this slightly more confusing; Inigo travels to become a Master in swordfighting by basically learning from every Master he could find. He returns to Spain to find Yeste, a friend of his father's who helped him first learn the sword. Yeste tests him and decides that he is better than a Master; he is a Wizard. However, as Inigo tries to find the six-fingered man, not only does he become a heavy drinker, he becomes bored of fencing. Hence Westley, who has more on the line, has been practicing more intently and is probably less rusty than Inigo wins.
    • Westley is significantly more intelligent than Inigo. This means he learns faster and is a better tactician. Also, there's a point in skill development where you can't get any better, only keep your skills sharp.
    • Actually, the book never outright states that Westley is more intelligent than Inigo; he is just a faster learner. Having studied only one thing for twenty years, Inigo is probably as smart or even smarter than Westley in regards to swordfighting, Westley just has a wider range of intelligence.
    • If Death can't stop True Love, what makes you think Inigo can?
    • Also, there's a difference between studying and fencing for sport as opposed to actual combat experience. Also, Inigo never said that he was learning for 20 years; he simply had 20 years of experience after learning. Heck, even 10 years of specific studying and practice would still be trumped by 5 years hands-on experience.
    • I doubt it was "hands-on" experience. It was probably the opposite. Inigo spent years learning to fight in any conceivable situation. He knew how to use uneven surfaces, trees, and all kinds of obstacles to his advantage, so that the Six Fingered Man couldn't escape by using an unfamiliar environment against him. Westley probably won because his training was all "here is a cleared out flat space on the deck for you to practice" type, which meant that in that one single environment he could win.
    • In addition to other points, Inigo and the Man in Black spend a few moments chatting hospitably before they fight and come to develop a respect for each other. Perhaps Inigo is, at least initially, holding back a little out of regard for a newfound friend.

    Surviving the Fire Swamp 

  • If no one's ever survived the fire swamp, how do they know there are exactly three dangers? At least the three I could understand, from myths and legends if nothing else, but what about the hypothetical clan of invisible dragons that lives in the middle, or the razorvine trees?
    • It's possible that people have left the fire swamp alive but with mortal wounds. Thus, technically speaking, the fire swamp DID kill them, just not immediately. They just happened to have lived long enough to tell the tale. Or perhaps they documented their travels through the swamp and someone found their documents.
    • Was it that no one had ever survived entering the Fire Swamp, or that no one had ever survived crossing the Fire Swamp? If it's the latter, people could've tried to cross it, then been forced to turn back by the three perils.
    • That ignores the point of the original question. If someone was undone by the three (known) perils of the Fire Swamp, but managed to make it out alive but mortally wounded, that's slightly more evidence that there's something in the swamp better at killing people than lightning sand, fire bursts, or ROUSs. On your other point, I only recall that Buttercup says "We'll never survive!" and the man in black replies "You're only saying that because no one ever has," and not exactly what the man in black says prior to it (whether living in the fire swamp, crossing it, or merely travelling through part of it).
    • Not necessarily. If someone made it out alive, but mortally wounded, certainly he'd mention what it was that mortally wounded him, eh? Perhaps he was walking along, and saw a fire spurt in front of him—he avoids it, but doesn't make the connection to the farting sound right before. A little later on, he's walking, and sees some white colored sand, but before he steps there, something falls in and immediately disappears, so he makes note not to step there. Then, just as he's about to leave, he's jumped by an ROUS, which mauls him to within an inch of his life, but he barely manages to escape, with the ROUS retreating back into the forest.
      Then someone finds him on the brink of death, and the man can only choke out the names of the three dangers, but doesn't last long enough to describe them in enough detail for people to avoid them.
    • But you (and Westley) are assuming that since three dangers are known, there are only three dangers. Look at it this way. I'm holding four cards in my hand, three folded out like a fan. One card is behind them, on its side so you can't see it. That card is, metaphorically, the hypothetical invisible dragons. It's possible that Westley was just saying three specific things since he'd seen three so far, and that the one Buttercup hadn't seen was just a myth in case they didn't actually encounter it, but it really sounded like the Three Dangers of the Fireswamp were a common legend (especially with Buttercup bringing up the ROUSes).
    • Well, there are two entrances/exits from the swamp. Going in one direction, you encounter A)the fire spurt, B)the sand, then C)the ROUS. From the other direction, it's C, B, A. So, someone from one side manages to tell someone else before dying that they encountered A & B, someone form the other side does the same with C & B, it's all put together eventually by the people who never go into the swamp. Easy as ABC. (Sorry)
    • Didn't the book say that once in awhile an ROUS would crawl to the very edge of the forest and die? So people could know about that. Plus, the Fireswamp could just have an overblown reputation, like the Dread Pirate Roberts. When telling about the swamp after all, saying "no one's ever survived" sounds a bit more interesting than "almost no one's ever survived, except for that one fellow from the next town over, his sister, the crone who may or may not have been a witch, and the fellow who also said he turned into a dog".
    • Although, this completely misses an important detail—Westley is not infallible. He could have easily just not known and been arrogant.
    • Assuming that the Fire Swamp is not that big (which, if the characters are using it as an albeit dangerous shortcut, it presumably isn't) and assuming enough people have entered and exited it over a long enough period of time for a reasonable sense of what is inside of it to be determined, there is only a certain number of things that can realistically be expected to be found in it. If enough people who enter and exit it before dying commonly talk about three key dangers, but little mention is made of any others, then it can be safely assumed that those three key dangers are the main ones that people need to worry about. If no one has mentioned the invisible dragons, then presumably no one has encountered the invisible dragons, which means they either don't exist or don't exist in sufficiently large or dangerous quantities to be considered a threat you're likely to encounter.
    • Who's to say that everyone who knew about the fire swamp went through it? Isn't it feasible that someone observed from the outside, taking notes?
    • The answer to the question, "How did Westley know there were only three dangers?" is obvious. He was reassuring Buttercup, so he deliberately avoided any hint that there might be more.

    Know about kidnapping 

  • Just occurred to me: How in Florin did Westley know that Buttercup had been kidnapped in the first place, and how was he waiting there when it happened, and where did he get his little sailboat? He parked the Revenge dozens of miles away and then sailed back, just in time to see the three grab Buttercup?
    • It's possible, being that he's a pirate, that he's privy to the same sorts of circles and information that someone like Vizzini is, and therefore heard either that someone was looking to kidnap her, or even specifically that Vizzini was. Or, I suppose you could just chalk it up to True Love leading him to her.
    • It's not inconceivable to believe that the Dread Pirate Roberts would maintain spies in the Thieves Quarter. The spy saw the transaction between Humperdinck's agent and Vizzini, then told Westley.
    • In the book, Westley is actually in the town square in disguise as Humperdinck is announcing the engagement and presenting Buttercup, who has been in hiding for the last three years training to be a proper princess, to the public for the first time. It is likely Westley was afraid he had been forgotten in the past five years (he does ask Buttercup why she didn't wait for him later) and was waiting for a chance to confront her and tell her everything he eventually tells her in the Fire Swamp. He was moving to do so when she was kidnapped by The Sicilian Trio, at which point he went back to town, told his men on The Pirate Ship Revenge to sail to an agreed upon point in Guilder (the far side of the Fire Swamp, perhaps?) ahead of him, stole a ship that one man could pilot and cut off The Sicilian Trio as they were heading for the Cliffs of Insanity, having overheard their plans as Vizzini explained things to Inigo and Fezzik, while he was putting the fabric from a Guilder Army Officer uniform on the saddle of Buttercup's horse.
    • Three years in the book, five years in the movie. Try to avoid confusing those who haven't experienced this story.
    • It's possible to be both, as all they said was that Buttercup had been trained for three years to a princess. Humperdink probably took Buttercup two years after she received word of Wesley's murder. She then spent the next three years in training.

    Title 

  • Why, exactly, is this story called The Princess Bride? Buttercup was a commoner. She wouldn't have become a princess unless she really had married Humperdinck, which never happened.
    • Or a bride.
    • In the book, Buttercup was given the title "Princess of Hammersmith" (some small lump of land on the back of Florin's holdings) after being discovered by Humperdinck, in order to shut up those nobles who would protest Prince Humperdinck marrying a commoner. This happened after Humperdinck went looking for the most beautiful woman he could find, following a brief and disastrous flirtation with an ugly princess after it was decided he needed to marry.
    • Actually, the princess was described as being perfectly lovely... it just turned out that she was as bald as an egg.
    • Funny catch. It could be an analogous construction to phrases like "the Queen Mother" or "the President-Elect." If I read a book called The President-Elect, I'd be surprised if the title character actually became President.
    • The author wrote the story for his two daughters. One wanted a story about a princess, the other wanted a story about a bride.
    • It's yet another subversion of fairy-tale themes. The heroes are fighting to prevent Buttercup becoming the Princess Bride.
    • Because The Princess Bride is a more memorable, succinct and cooler fairy-tale style title than The Commoner Who Isn't A Princess Yet But Will Be When She's Married Bride.
    • Prince or Princess is a noble title like Duke or Duchess - a king can grant the title to anyone he chooses. It's just become associated with the king's children because traditionally the king's heir is granted the title to gain experience ruling before becoming king himself. It makes sense for the king to grant Buttercup the title of Princess for the same reason, since she is betrothed to the crown Prince.

    Revenge 

  • Why is The Pirate Ship Revenge waiting for Westley and Buttercup on the far side of the Fire Swamp? Even if you assume that Westley managed to find out Vizzini's plans as well as where they were heading (possible, as discussed in the scenario above) and stole another ship one man could pilot so he could give chase, his plans didn't include going cutting through the Fire Swamp and he had no way of getting word to his men on The Revenge to rendezvous at another point.
    • It could be that a natural cove near The Fire Swamp was a routine hideaway for Westley and his men between jobs. He could have been planning to cross overland AROUND the Fire Swamp to "the usual place" but Buttercup's pushing him into the ravine forced him to change plans and take the riskier path since the ravine was steep enough that he couldn't get himself AND Buttercup out of it before Humperdinck caught up with them.
    • If you read the book, it mentions that the original plan was to go around the fire swamp, but they fell into the ravine (more accurately, Buttercup pushed DPR, found out he's Westley and jumped after him.) After falling in, there wasn't enough time to climb back out before Humperdinck caught up to them,even if Buttercup had the physical ability.

    Life draining machine 

  • Having been through Count Rugen's life-draining machine, and having had 50 years drained away, won't Westley's happily-ever-after with Buttercup be incredibly, depressingly short? After all, he's about the equivalent of 70-something years old.
    • The Miracle Pill's got that covered.
    • And even if not, Miracle Max could always whip something else up.
    • In the sequel, Pierre from Westly's ship fixes him up. Dur?
    • Even ten or fifteen years being happy with each other is a much better ending than her being married to someone else by force and both being killed on that day. Think of it as a bittersweet ending, if you will, but everybody dies eventually.
    • The Machine is obviously still in the testing phases. Count Rugen couldn't have possibly done the required scientific testing to know with that degree of accuracy how much life he was draining away. Take what he says as hypothetical.
    • Or, if you'd like, Buttercup lost that many years off her life out of her own grief. "A part of me died that day!" anyone?
    • Or, draining his life away is completely different from rapidly aging him, since he obviously didn't age. Perhaps it's a life-reversing machine, and so if it sucks away more years than you are old, it kills you?

    Magic pill 

  • Is Miracle Max's miracle pill actually magic, or is it just a massive dose of caffeine that knocks Westley out of a coma? The "Do you think it'll work?" / "It'd take a miracle." exchange between Max and Valerie certainly seems to suggest that they don't think he's got any magical powers at all.
    • Well, the exchange may be referring to the pill, or it may be referring to their plan (it comes right after "Have fun Storming the Castle!", after all). As for what it's made of, the book has a sequence where the editor mentions Inigo and Fezzik having to fetch the ingredients, but he cut it for being boring.
    • The "it would take a miracle" comment was in reference to their plan to rescue Buttercup. That was blatant. Miracle Max had lost his confidence in his abilities, yes, but he lit up like a Christmas tree upon the prospect of getting revenge on Humperdinck for firing him, and the only reason he had lost confidence in himself was because he had developed a psychological block. An expert gunslinger who fails his team and gets kicked out by the tyrant who pulled rank and took over may no longer believe he can shoot straight anymore, but that doesn't mean he suddenly disbelieves that his bullets themselves work.
    • The Miracle Pill is magic. The music when Inigo gets his Heroic Second Wind is the same as when he kissed the pill before giving it to Westley.

    "I do" 

  • I'm going to have to get it out of my system. I know that the setting is fictional and the year undefined, but the legal requirement for both parties to say "I do" was championed by Queen Victoria in the 1800s to combat sham marriages which were being used as a cover for selling women into slavery.
    • Westley is progressive.
    • Mm...intentional anachronisms, first off (Goldman spends several paragraphs hypothesizing on why the book says, for example, "this was before Europe" but "after France", and "after taste, but only just", etc.). Second, if you look at some of the things, it does look like an...interesting world, the only way to explain everything is that it's an AU. Therefore, it is possible that social stuff moved forward quicker. Alternatively, Westley's even better than one would think, and a specific law was made in this timeline for noblewomen so they could not be forced into marriage. Buttercup became Princess Buttercup, so either she has the right or she's common and can't marry him anyway. But I digress.
    • The book is set "after America", and assuming that Europe's non-existence didn't screw up linear time too badly, than the story could very well take place in the 1800s (America, after all, was founded in 1776.) In fact, the lack of Europe doesn't necessarily mean the countries therein don't exist, only that the continent hasn't been named—meaning it's perfectly plausible for Victoria to be ruler of England and champion the concept of "I do". So basically, all that is required for this bit to make sense is for you to assume that it is the 1800s and that Europe, the continent, is not given that name.
    • Perhaps S. Morgenstern means 'Europe' as a unified entity, i.e. before the formation of the European Economic Community or something similar?
    • Alternatively, Westley is going with the spiritual definition rather than the legal one. Legally, the marriage is the least of their problems given that Westley and co just stormed the castle. (As it turns out, in the book, they are indeed on the lam after these events).
    • It's basically Morgenstern / Goldman creating a romantic, fantastical "once upon a time" fairy-tale atmosphere for the story. Like George Lucas opening Star Wars with "A long time ago in a galaxy far, far away..." despite the fact that it's clearly set in the future — we're not really supposed to think about it too hard or try to literally put it together to see when it's set, we're supposed to just take it as read that this is basically a fairy tale we're reading / watching, and not to worry too much if things don't quite make sense or the history isn't quite right.
    • Always thought it was supposed to be him trying to comfort her because, to him, it didn't matter if she was legally married to another or not. He's a pirate, a wanted man who's broken plenty of laws, and is by all legal counts dead (or at least "Wesley" has been considered dead for five years). Doubt he cares much if some small country they're never planning on returning to considers the woman he's planning on spending the rest of his life is technically married to another. He only says that about it not counting because Buttercup seems worried, and because, in his mind, as long as she doesn't want/agree to the marriage, than it doesn't count.

    Loving Buttercup 

  • Why does Westley love Buttercup? She wasn't nice to him when they met, she's dumb as a doornail, she doesn't have any real personality at all; really the only thing going for her is that she's pretty. There doesn't seem to be anything to love but a pretty face. Westley is smart, handsome, charming, daring, athletic and really deserves better. Is he just shallow?
    • The heart wants what the heart wants, and True Love is blind.
    • She's a satire of your average princess in your typical fairy tale; for example the personalities of the pre-renaissance Disney Princesses were not all that interesting anyway. If nothing else I thought Robin Wright did a great job bringing out life to a slightly unwritten character.
    • They spent their adolescence together. Anyway, Buttercup must have something going on in her head if she can whip off that True Love speech note  on the spur of the moment.
    • It's equally confusing why Buttercup would love him, when he literally never said more than three words to her up until the day she declared her love for him, and once he does start talking he continuously insults her intelligence (yeah, she is dumb, but you don’t keep telling the girl you supposedly love that she's an idiot, or start that right back up again after years of separation) then is gone a couple hours later. Ignoring Buttercup's Baby, I don't see this relationship lasting a week once they actually have to start interacting like normal people and get past how hot the other is.
    • They just love each other and junk. She's not just a powerless mannequin, either, with the I-AM-THE-QUEEEEEEEEEEEN! thing.
    • It's a parody of fairy tales. Fairy tales constantly have people falling into true, passionate, unbreakable love with each other on flimsy pretexts, and the humour in this case comes from the author spelling out just how flimsy the pretext is in this case. You might as well ask why Snow White marries the prince just because he wakes her from her cursed sleep, because it's not like she knows him before this. Either accept it or don't, but it's just how these kinds of stories go.
    • Also, in the book it's mentioned that Buttercup's parents were constantly quarreling and bickering with one another yet still seemed to genuinely love one another. To the extent that when her father died, the general consensus of her mother's death not long after was "the lack of competition" in their arguing. So it's possible to her that this all is just the kind of banter that a loving couple actually has.

    Guards on the gate 

  • After Fezzik revives Inigo, he tells him that the castle gate is guarded by thirty men. "How many could you handle?" Inigo asks. "I don't think more than ten." Inigo then counts on his fingers to figure out that that leaves 20 for himself. Yet later, when Inigo, Fezzik and Westley scout the castle gate, Inigo looks over the wall and says, almost immediately, that it's guarded by sixty men.
    • Watch the movie again. Shortly after Inigo and Fezzik discuss the 30 guards, there is a scene where Humperdinck demands that the number of guards be doubled, as part of his fake efforts to protect Buttercup's life.
    • Still doesn't explain why Inigo had to count on his fingers to figure out the 30-10 and yet can count almost immediately 60 men.
    • He might still be a little drunk in the first scene but sober by the second.
    • The first case, he's doing subtraction. In the second case, he's just counting people.
    • When they arrive at the gate, Fezzik actually points out, "There's more than thirty!" Inigo responds, "What's the difference? We've got [the Man in Black]!"
    • I always took the bit with Inigo having to spend time counting down from 30 to 20 to be a joke at his expense, underscoring his lack of intellect/education, while later at the gate he has more time to count and the people right in front of him. The fact he was still recovering from being drunk in the first scene and not the second also helps.

    Murder Plan 

  • Am I the only one who has a problem with Humperdinck's murder plan? It relies on everyone assuming Guilder is responsible by way of Guilder insignia to be found on Buttercup's corpse! Does he really think he rules a country full of idiots?!
    • What, are you expecting that he was going to let all of the citizenry examine the corpse? The Guilder insignia was part of the excuse; all he'd really need to do, for his people, is say, "Agents of Guilder kidnapped and murdered the Princess." It's not like he was going to call in CSI.
    • Also, in the movie, the whole idea of going to Guilder to kill her was so that her body would be found far from where she was supposed to be, murderered, in the kingdom of an enemy. It's the difference between stabbing someone and writing a confession for an enemy and killing them in the enemy's house with his own gun.
    • Plus since Humperdinck was going to do the deed himself, he could just say he actually came into the room and saw the Guilder assassin leaping out the window or somesuch, providing his own eyewitness testimony. Who'd argue? He's the prince.
    • From the fact that Guilder is described by Vizzini as the "sworn enemy of Florin" and that Humperdinck was convinced Buttercup's death by Guilderians would make the people "demand they go to war", it seems to me that even if the people had gotten to see the uniform/insignia, their irrational hatred of Guilder and love for Buttercup would have overridden any doubts they might have had about the prince's story.

    Murder Plan, part 2 

  • My issue is with the original plan. So Humperdinck hired Vizzini to kidnap and then kill Buttercup, right? And Rugen was in on it, but not the rest of the guard or the king. So he had to put on a show of looking for her and catching the kidnapper. But he never expected to actually find her, right? But then he realizes that someone else has interfered, and so now he has to find her for real, just in case the new kidnapper doesn't kill her?
    • He expected to find her dead—someone interfering is a monkey-wrench in his original plan, so he has to keep up pursuit, if for no other reason than to identify what the hell is going on. He has no idea what the Man in Black is up to. The Man in Black might be looking to expose his plot, or who knows what. Frankly, he has to pursue because by that point the plan's gone so far off the rails he has to do some kind of damage control.
    • Remember that he isn't just trying to have Buttercup killed, he's trying to frame the neighboring country of Guilder for the murder so he can justify a war. Even if the Man in Black kills Buttercup for him, if he doesn't kill her in a way that implicates Guilder then that's the whole plan down the crapper.
    • There's a reason they say no plan ever survives contact with the enemy. This one certainly didn't.

    JRPG 

  • Anyone else notice that Morgenstern's original version fits the JRPG genre to a T? Lots of fighting for Westley as DPR on his ship, Westley and Buttercup spend days in the Blood Swamp (fighting giant rats no less), Inigo and Fezzik have to crawl their way through the five floor Zoo of Death filled with monsters, Miracle Max sends them to fetch a bunch of ingredients to revive Westley, they actually have to fight a lot of the guards when they storm the castle, and it's implied that there was a lot of further fighting that was cut for not progressing the plot.
    • You know, I did always think the movie bore a resemblance to something from Final Fantasy.
    • The Blood Swamp? And days? It's the Fire Swamp, and it was probably only hours. ???
    • Your standard JRPGs and The Princess Bride share influences from similar sources, such as fairy tales and fantasy fiction, where such kind of exotic and unusual quests, characters and settings are commonplace.

    ROUS 

  • Westley says he doesn't think that the ROUS's exist... but about thirty seconds before, he was looking right at them.
    • Pretty sure he was just trying to reassure Buttercup.
    • Yes, he was. This is explicit in the book.
    • Even in the film, he very clearly sees the ROUS’s around them before telling her he doesn’t think they exist—obviously a lie to keep her from panicking.

    Westley leaving 

  • When Rugen runs away from Inigo and locks a door behind him, Inigo tries in vain to smash the door, and desperately asks Fezzik for help. Fezzik props Westley up on a suit of armor, holds Inigo back, and smashes the door open. He couldn't have been apart from Westley for more than a minute or two tops, but when he goes back, Westley is gone. How in the world could he have gotten into Buttercup's bedroom ahead of her, when he had no strength?
    • Rule of Cool.
    • In the book, Westley could already walk feebly and Fezzik had to hit the door three or four times to knock it down and then had no idea which corridor Westley had gone down. In the movie, Westley may have had Fezzik carry him and then given him a distracting quest so that he could face Humperdinck and reunite with Buttercup alone.
      • Indeed, Andre the Giant was supposed to hit the door three or four times like book!Fezzik did, and you can actually see Mandy Patinkin's surprise when Andre instead breaks the prop with only one hit.
    • Westley MAY be regaining his strength, but only gradually over time. Westly PROBABLY crawled through the corridors to get to the honeymoon suite (how EXACTLY he knew, don't ask me), and laid on the bed so he can rest until Buttercup arrives. When Westley does confront Humperdink, he DELIBERATELY gave him the "To The Pain" speech to not only stall Humperdink while still regaining strength, but also to tell him that there are fates that are much worse than death. So Westley (literally) stood up to Humperdink, sword he was carrying pointing right at him, making Humperdink quite intimidated. Barely able to stand for about less than a minute, Westley demands Buttercup to tie him up to a chair, so when they leave, Humperdink will realize Westley's right, he'll be left in anguish and misery for the rest his life. By the time the gang left the kingdom, Westley will have his strength restored, probably with some side effects.

    Time between summation 

  • How did it get from completely light to dark enough to need torches and a fire in the half hour between Inigo's summing up and the wedding?
    • Because Inigo is really, really bad at "summing things up"?
    • Also, they could have intentionally waited for night to fall. After all, the whole burning cloak thing would undoubtedly be more impressive in the dark than in broad daylight.
    • It's still light when they leave the wall. "Buttercup is marry Humperdink in little less a half an hour." Half an hour is plenty of time for the sun to set, depending on time of year and latitude. Also, the wedding may be scheduled to start in half an hour, but the ceremony itself could take an hour or more. And they have to go get the wheelbarrow and the few other things (the candle to light Fezik on fire) they need for the plan to work. That would easily eat up the time before sunset, and they still start their run on the gate almost exactly as the wedding starts. If Humperdink hadn't insisted to "Skip to the end," they may very well have crashed the wedding itself and carried Buttercup off from there.

    Murder and the succession 

  • Isn't conspiring to kill Buttercup at that time rather stupid? The reason Humperdinck needs to get married is because his father is dying and he needs to secure the succession. Killing his bride before or just after the wedding might get him the war he wants, but still leaves him with an unsecured succession. Wouldn't it be better to get Buttercup to provide him with an heir so that he doesn't have to worry about that and then murder his wife to provide him with a pretext for war?
    • The Prince could have literally any girl in the world. He might have to secure the succession, but he wants the war now.
    • Buttercup's not there to bear any children for Humperdinck — she's the most beautiful woman in the world, and the people adore her. Former commoner — incredibly beautiful — murdered on her wedding night — tragic. Humperdinck picked her out to be the perfect martyr, so much that her death would make the people of Florin rally to war. Once the war is well underway, then he can pick wife #2 at leisure.

    Ultimate Suffering 

  • When Wesley is screaming the Sound of Ultimate Suffering, Inigo tells Fezzik he knows it's the Man in Black because "his true love marries another tonight." How does Inigo know that Wesley/the Man in Black is the True Love of Buttercup? The whole of their interaction before that scene was the duel, and the majority of their conversation during that was informing each other of how they weren't left-handed.
    • Perhaps Inigo is Genre Savvy enough to realize that no man in such a fairy tale land could have accomplished all the inconceivable feats the Man in Black had except to save his true love.
    • Also, Fezzik was filling him in on the details while nursing Inigo to health.
    • Specifically, on the eve of the Royal Wedding, who in the land has cause to cry out with Ultimate Suffering but the man whose true love is, in fact, the Royal Bride?
    • Fezzik was part of the brute squad. He probably heard a lot of what was going on from guards, who had witnessed the scene where Westley and Buttercup emerged from the Fire Swamps and Westley was arrested and then knocked unconscious after noting Rugen's six fingers. Given that Inigo gets all the details from Fezzik, he didn't have to be Einstein to figure out what was going on, and that if there was a shattering scream from deep underground, it was probably the Man in Black being tortured.

    Five kisses 

  • Fridge Logic, and certainly deliberate: there are five kisses that "everyone" agrees deserve full marks, and this one left them all behind. There most have been some really infallible witnesses to those kisses for historians to be able to compare and judge them like that.
    • It's like the list of the World's Most Beautiful Woman, which is brought up all the time in the books. What standard of beauty are they using? Who's keeping track, when we have candidates all the way from England to India? How long is the list? Who is keeping this list?
    • It's a parody of fairy tales. Fairy tales are filled with characters who are apparently "the most beautiful woman in the world" and are exchanging perfect, love-defining kisses with each other and the like, despite all of that being entirely subjective and depending on the people involved and the culture they live in. In this case, it's taking the concept to the extreme of suggesting that, if the author is to be believed, someone has apparently gone around chronicling and ranking the best kisses ever regardless of how pointless and meaningless such a list would be. It's absurdism. We're supposed to chuckle at the ridiculous idea of someone (probably with a clipboard) going around measuring people's kisses and ranking them, not querulously demand to know what empirical framework he's basing it on.
    • It is also a way to tell a pre-teen boy that a kiss was supposed to be passionate without having to actually describe the kiss.

    Missing father 

  • The boy's father is probably either dead or absent for some reason. At the beginning, the grandfather says that his father (the boy's great-grandfather) used to read him The Princess Bride when he was sick, and he used to read it to the boy's father when the boy's father was sick.... so if it's a father-to-son tradition, why isn't the boy's father around to read the book to him?
    • Probably working. The son was sick off from school.
    • Or perhaps he didn't have a son to read it to?
      • To expand on this, it's possible that he is the boy's maternal grandfather, and therefore the boy's father is not a blood member of the family and didn't "inherit" the tradition.
      • But the whole point of this Headscratcher is that the boy's father did inherit the tradition, since the boy's grandfather said he used to read it to his own son — the boy's father. The question is why the boy's father now isn't around to read it to him.
    • Who says it's even a tradition, especially? The grandfather mentions that his father read it to him, and then he read it to the boy's father, but that's it. From the sound of that, it's not exactly an ancient tale that's been passed down from father to son from time immemorial here, there's no sense of "my father, and his father before him, and his father before him...". It's one man retelling a story he enjoyed hearing from his father to his son and grandson. It's not necessarily a certainty that there's tragedy or abandonment here; perhaps the boy's father simply didn't consider it to be a tradition that he pass it on to his own son. I mean, do you feel tradition-bound to read every bedtime story your parents told you as a child to your own children? Heck, the grandfather might not even consider it a tradition particularly; he's visiting his sick grandson, wants to do something nice for him, and remembers back to when he'd read his son a storybook and decides to do the same, but dresses it up a bit when selling him on it to make it seem a bit more special.
      • Not to be too pedantic, but from the boy's perspective, it is literally "my father, and his father, and his father before him".
      • Technically yes, but again — the grandfather's likely just framing it that way to make it sound a bit special for his grandson. That doesn't make it actually a family tradition that's rigidly set in stone, the way this headscratcher is presuming (though it could certainly become one over time). The fact that this grandfather had this story read to him as a child and consequently decided to read it to his own son doesn't mean it's become a fixed-in-stone family rite-of-passage that a father must pass this story down to his son, and that a failure to do so is indicative only of a major family upheaval that means the father is either dead or absent. It simply means that the grandfather liked this story as a child, liked reading it to his son, and thought his grandson might like it as well. There are any number of possible reasons why the father never read it to him that don't hinge on him either being dead or absent. Maybe the father didn't really like it but didn't want to upset the grandfather. Maybe the boy's mother always read him a bedtime story instead of his father. Maybe the father always meant to but kept forgetting to get the book, and the grandfather finally decided it was a good opportunity to bring it around. Maybe the father had forgotten this particular story (do you remember every story your parents read to you as a child?). Maybe the father asked the grandfather to read it to the boy because he thought the grandfather would tell it better. Heck, maybe this family simply didn't really do bedtime stories up to this point. There are any number of possible explanations.
    • This is all explained by examining the differences between the novel and the film. The conceit of the novel is that the author (now an adult) is abridging a political treatise his father (who is originally from Florin) read to him when the author was young. Like the grandfather of the film, the father skipped boring parts and just read "the good stuff," and the author regularly interrupts the story to let the reader know which parts he's editing or cutting completely. The film dropped the abridgment conceit and and replaced the authorial interjections with scenes between the boy and his grandfather. The grandfather was likely aged up because the original telling would have been in the late 30's/early 40's, when Goldman was a child. The modern day portions of the film take place in 1987, over a generation later. A 40 something in 1973 can have an immigrant father without issue, but they decided to make it a grandfather to a boy in the 80's.

    Time 

  • What time is the story set in? Most people assume it is sometime in the Middle Ages, but Vizzini says at one point, "Australia is entirely peopled with criminals." Australia wasn't discovered by Europeans until the 1600s, and didn't become a penal colony until the late 1700s.
    • The book is an unapologetic Anachronism Stew which drove editors insane in footnotes. Don't even try. That way lies madness.
    • As a for instance: The book is set after America, but before Europe, but after France, but before Paris, but after blue jeans. . .

    Battle of Wits rules 
  • The rules governing the Battle of Wits have a serious flaw, even if we disregard Westley's gambit. If the person trying to guess the poison's location (in this case Vizzini) guesses correctly, then the person who placed the poison (in this case Westley) would be knowingly committing suicide by agreeing to drink. Many people would simply forfeit the game at that point, and neither man would die—but nothing would get accomplished, and the two men would be back to their original impasse. That's why Vizzini tried to secretly switch glasses—so that Westley wouldn't know he was drinking from the poisoned cup. (At least that's what Vizzini thinks.) The game would make more sense if it allowed Vizzini a chance to pick up the glasses, move them out of Westley's sight for a moment and then choose either to switch them or not to switch them. That way, neither man could be sure where the poison is located, and both would be more likely to drink.
    • The game isn't being played in a vacuum. Vizzini still has the knife to Buttercup. If Westley knows he's about to drink the poison and tries anything, Vizzini will kill her. That's kind of the whole point of the exchange.
    • Additionally, the terms of the game were set by Westley, who already knows it doesn't matter which of them drinks from which cup, and has no reason to worry about being poisoned. The rules are designed to play into his gambit. The real object of the game is to get Vizzini to drink from either one of the cups; the rest is purely misdirection.
    • Where are you getting these rules from? Vizzini's mistake was to assume that there were rules, and the game was fair.
    • The game was totally fair. Nowhere does Wesley say Vizzini has to drink from the cups on the table either. Had Vizzini guessed correctly, there was a third option made available to him.
    • Westley states the rules as follows: "Where is the poison? The battle of wits has begun. It ends when you decide and we both drink." Vizzini's mistake was in assuming more rules than were stated. He assumed his only choices were the two goblets (which is exactly what Westley was banking on), but he could just as easily have chosen to drink from the bottle or from some other source that he knew Westley hadn't tampered with, without violating the rules.
    • Wesley could have proposed to let Vizzini mask the cups before they drink to put him more at ease with the belief that the terms of the game are fair and better sell his deception. If Vizzini had proposed this rule change, Wesley would of course have agreed readily, since he knows it wouldn't change anything. From Vizzini's perspective, however, he believes that Wesley might refuse the rule change and be unwilling to give up his unspoken get-out-of-poison-free card. Then they'd be at an impasse again. The better play from his perspective is to simply trick Wesley into unknowingly drinking the wrong cup, which is what he tries to do.

    Captain of the Guard 

  • Exactly what level of bravery must the guard captain have to refuse to run at the sight of a giant, cloaked, seemingly floating, burning apparition, as all of the other guards did, and yet hand over the gate key after being threatened by a less ominous brute seconds later?
    • What kept him there wasn't bravery. It was being too scared shitless to think straight — you see that he tries to get away, but thinks he's hemmed in and surrounded. He wasn't standing his ground so much as he felt backed into a corner.

    The Ending 

  • The Prince's original plan was to have Buttercup abducted and murdered, so that he has a pretext for a war with his neighboring country by framing them. At the end of the movie, Buttercup is taken away and several people died, including Count Rugen. So the guy basically gets what he wanted in the first place, served to him on a golden plate by Westley & Co., right?...
    • Remember how the group made their grand entrance? By storming the gates and making sure at least 60 men — and anyone else within earshot — know the Dread Pirate Roberts was attacking. Not Guilder.
    • Which actually changes very little. Humperdinck is a prince, a ruler - it's enough he claims that Roberts was hired by Guilder and hardly anyone in his kingdom will challenge this.
    • Except the Dread Pirate Roberts has a very clear, very strong reputation — one that makes it very unlikely that he'd be a mercenary for Guilder. Also, if Humperdinck had that kind of power, he wouldn't have felt the need to go through the whole sham of having Vizzini planting evidence of Guilder's involvement. He clearly thinks he needs some solid justification.
    • The plan called for people to get so outraged over the death of Buttercup, their beloved and beautiful princess, that they outright demand war. It's unlikely that they're going to be quite as outraged and in a mood to go to war over the death of Rugen, Humperdinck's creepy mate who liked to torture people. Not to mention that it's implied that the whole affair is going to leave Humperdinck, if not discredited, then having taken some significant dents to his reputation as a result ("Let him live with his cowardice."), meaning that people aren't necessarily going to blindly trust what he has to say.

    When do you have time to develop the immunity to Iocaine 
  • Are we expected to believe that the old Dread Pirate Roberts trained Wesley to be immune to the powder? Where would that fit on the priority of things to teach your prisoner?
    • Old Roberts was probably grooming and training Westley to be his successor for, if not the whole time, then a fairly substantial part of their time together. The whole "I'll most likely kill you in the morning" stuff was just an initial threat that clearly just became a routine in-joke between them. So most of what Westley was doing on the ship was just part of his training, even if he didn't initially realise it.
    • Also, Iocaine is by its very nature almost undetectable. Roberts could have been dosing Westley with the stuff from the very first day they met without Westley even realising if so he'd wanted. It's not like they necessarily needed to block out special "immunity from Iocaine" sessions.

     Is this Earth or a fantasy world? 
  • The main two countries in the story’s narrative are the fictional countries of Florin and Guilder. Now, these may just be fictionalized versions of Italy and Germany, as many have already theorized, but fictional countries all the same. But Vizzini is from Sicily, a very real country on Earth. So… Does the story take place on a fictional fantasy world or does it take place on Earth?
    • It's a Ruritania.
    • The book is somewhat more explicit that Florin and Gilder are located in Continental Europe, but even the movie makes mention of several real-life countries and nationalities (Greenland, Australia, Spaniards, Sicilians; Fezzik in the book is said to be from Turkey). So no, it’s not a fictional fantasy world, just fictional countries within our world.

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