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9* ''Literature/AgathaHAndTheVoiceOfTheCastle'': Castle Heterodyne, a mad artificial intelligence built by an even madder scientist from a line of mad scientists, all complete raving villains to a man, has no idea why the Heterodyne Boys, the closest thing to a BigGood the setting has, were never impressed despite its many, many attempts to please them. The fact that it killed their mother, a literal saint of a woman, never seems to register with it.
10* ''Literature/{{Animorphs}}'': At the end of [[VillainEpisode VISSER]] it's revealed that Visser One cannot understand the concept of love, in spite of having lived among humans for years and even going so far as to bear children and have a family.
11* ''Literature/BazilBroketail'': Heruta seems absolutely incapable of empathy towards others and is deeply shocked when he finds out that Relkin actually acknowledges that Padmasan servants he kills -- like imps -- are actually sentient beings. He commends the dragonboy for his natural compassion for other living beings, but it's pretty clear that he doesn't mean any of it and the entire concept is completely alien to him.
12* ''Literature/BelisariusSeries'': Half the reason why the BigBad has trouble defeating Belisarius: Link can understand self-centered aristocrats just fine, and can handle groups based on statistical analysis, but an individual acting for the good of humanity? Not so much. (The other half is that Logic Cannot Comprehend IndyPloy.)
13** Link is ultimately defeated because it can't comprehend the concept of trust: [[spoiler: Belisarius traps Link in a strategically pointless campaign, far from where the outcome of the war will be ultimately decided, and out of communication with the center of the Malwa Empire. Link could, at any time, get out of the trap by having its current host body killed and reincarnating in a new host but doesn't until far too late. It couldn't conceive of its enemies' greatest commander trusting in his allies to win the final battles while he was content to merely keep Link occupied far from the main action.]]
14* ''Literature/BloodMeridian'': Judge Holden, the most cruel and depraved character in a story already full of cruel and depraved characters, seems to be honestly confused as to why would anyone oppose or disagree with his philosophy of perpetual conflict, murder and bloodshed. "War is God" and anything that opposes it must be destroyed. His pursuit [[spoiler: and ultimate killing]] of the Kid (who already was a murderous thug, anyway), seems to be warranted by his ability to still show some mercy and kindness, and failing to completely fall to his most violent urges, as others in the Glanton gang had done.
15* ''Literature/BrimstoneAngels'': As a devil, [[TokenEvilTeammate Lorcan]] is MadeOfEvil, and was raised in the LawfulEvil society of the Nine Hells, and it shows in how he interacts with everyone, especially main heroine Farideh. Namely, he always defaults back to manipulation, gaslighting, and outright blackmail, even of people who are nominally on the same side as him. Even Farideh, whom his POV chapters confirm he ''does'' care about and feel affection for (in his own, somewhat twisted and possessive way), but he simply can't fathom a relationship that ''isn't'' based around power, control, and one party dominating the other.
16* ''Literature/ChanurNovels'': Played with. The AlwaysChaoticEvil kif ''know'' that other species have empathy, morals and other things [[BizarreAlienPsychology lacking from the minds of kif]]. Kif who deal with other species study up on these things in order to try to use logic to predict what other species will do, but still fail more often than not due to lacking any intuitive understanding of the topics.
17* ''Literature/CiaphasCain'': In ''Duty Calls'', a renegade Inquisitor is quite [[KnightTemplar certain]] that Cain will appreciate why he acted as he did. Given that this included staging a massacre, abandoning innocents (including children) to an alien attack, summoning an alien attack to hide his tracks, and no less than three attempts to assassinate Cain, this does not work as expected; even a self-professed DirtyCoward like Cain is horrified. Justifying his actions with a blatant QuoteMine of Cain's favorite religious text (removing the second half and reversing the meaning) didn't help his case.
18* ''Literature/CodexAlera'':
19** Explicitly pointed out in the second book when the Vord Queen that Amara, Bernard, Doroga, and their forces are fighting ends up caught by surprise and killed because, while she ''technically'' understands the concept of sacrifice, she just can't get ''why'' people would be willing to throw their lives away to prevent her threat to the rest of the world.
20** In the next book, ''Cursor's Fury'', the principled Amara and the ruthlessly pragmatic Invidia Aquitane are interrogating a captured spy named Rook who is working for the traitorous High Lord Kalarus. Amara manages to figure out the source of Rook's apparent loyalty to him: Kalarus is holding her daughter hostage to ensure compliance. Once Amara realizes this, she does the last thing either Rook or Invidia expects: she offers to rescue Rook's daughter, because it is the right thing to do. Rook immediately breaks down in tears of relief, while Invidia stares at the whole thing, seemingly unable to comprehend what happened because it doesn't fit into her ruthless and calculated mindset.
21** Used twice in the fourth book, ''Captain's Fury''. High Lord Kalarus is explicitly said to be ignorant of anything that isn't himself, while [[SmugSnake Senator Arnos]] firmly believes that Tavi is an opportunistic politician like himself who only ''pretends'' to be TheGoodCaptain for PR reasons, when Tavi is actually the genuine article.
22** This is something of a theme in the series. In the final book, the Vord Queen devotes much of her effort to comprehending good (or at least, humanity) but largely fails, possibly because the aforementioned Invidia is her "teacher". [[spoiler: She learns just enough to get a legitimately moving AlasPoorVillain moment at the end, though]].
23*** And then there's the young Vord Queen born near the middle of the book, who doesn't even understand that good is a thing that can be comprehended. When told that the communal dinner she, the main Vord Queen, and Invidia are having is for [[ThePowerOfFriendship creating bonds between them]], she wonders [[LiteralMinded why they need restraints]].
24* ''Literature/TheCountOfMonteCristo'': The exposed criminal Caderousse begs for "mercy", by which he means "help me to escape all consequences of my thievery". The funny thing is that he's not being disingenuous. He ''really thinks'' that that's the definition of mercy. He can't understand why anyone would want forgiveness on an emotional -- as opposed to just legal -- scale.
25* ''Literature/CradleSeries'':
26** The world runs on AsskickingLeadsToLeadership and MoralMyopia. Therefore, ''many'' people are repeatedly confused when the main characters are actually ''nice''. In the earliest books this mostly revolves around Eithan, who is the strongest around by orders of magnitude. At the end of ''Soulsmith'', he is fully within his rights to murder all the people who have been hounding Lindon and Yerin for the entire book, but instead he lets them keep all the treasures they had earned (including by far the most powerful) and even lets one of them demand a completely hypocritical honor duel against Lindon. No one understands why he did this, and later they claim that everything could have been avoided if Eithan had just revealed his identity sooner, which is manifestly untrue -- when he revealed his identity, they kept fighting until he forced the issue.
27** This comes to a head in ''Bloodline'', when [[spoiler:Lindon finally returns home to save his clan. His clan ''cannot'' comprehend that he is there to save them, assumes the coming disaster is just some sort of trick, and try to murder him out of sheer, anarchic idiocy. The First Elder, who was a ReasonableAuthorityFigure for Lindon growing up, even chastises Lindon for concocting this revenge scheme, because he can't understand how someone as mistreated as Lindon would ever want to save them. The only logical explanation is that he's trying to humiliate them and steal the clan]].
28* ''Daniel and the Devil'': In this Eugene Field novel, [[TheFettered ordinary decent businessman Daniel]] simply doesn't see the appeal of a life of fun and debauchery, being a respectable businessman and father of nine. The Devil is so flabbergasted by this that he eventually [[spoiler:breaks his bond with Daniel, effectively releasing him from [[DealWithTheDevil his contract]] AND letting 1001 souls go free from Hell]].
29* ''Literature/DarkshipThieves'': Thena's father. When he has captured both Kit and Thena, it does not occur to him that Kit has hostage value until she threatens to kill herself if he harms Kit.
30* ''Literature/DavidCopperfield'': Uriah Heep hires Mr. Micawber as his clerk, on the assumption that paying off his debts and providing him with financial security will be enough leverage to stop him protesting against Heep ruining the Wickfields' lives. Actually, Micawber's horrified, and uses his position to recover important documents to bring Heep down.
31* Literature/{{Discworld}}:
32** The New Death from ''Literature/ReaperMan'' is absolutely baffled that Miss Flitworth was willing to [[spoiler: share her lifetimer's sand with Bill Door, the previous (and good guy) Grim Reaper]].
33** Reacher Gilt from ''Literature/GoingPostal'' doesn't seem to understand the concept of trust or belief at all and just marvels at how easy everyone else is to fool. [[spoiler:He also doesn't understand Vetinari's 'angels' speech, [[IDieFree which leads him to choose the door]].]]
34* ''Literature/{{Dragaera}}'': In the book ''Issola'', while not evil necessarily (more like inhuman AbusivePrecursors), Vlad notes this about the Jeonine. They hire him to {{kill|TheGod}} his patron goddess Verra (whom he's rather annoyed with at the time), and he comments to his friends how they obviously have no understanding at all of humanity, to think he would actually do this.
35* ''Literature/DragonBones'': None of the villains is able to understand that some member of the Hurog family would ''not'' kill or otherwise sacrifice their own family members in order to become Hurogmeten instead of the Hurogmeten. Thus, Ward is easily able to pretend that, of course, he will kill his uncle to get the castle back.
36* ''Literature/TheDresdenFiles''
37** ''Literature/DeadBeat'':
38*** Works against the heroes when Harry says that [[spoiler:Waldo Butters]] doesn't know anything, but then risks his life to save him. Thomas points out that Grevane won't believe he would do that out of [[PowerOfFriendship friendship]] -- Grevane will assume Butters still has some practical value and continue targeting him.
39*** [[spoiler: Lasciel's shadow]] simply cannot understand why Harry wouldn't want to be like Nicodemus, and in later books can't get that Harry is quite willing to die rather than pick up her coin -- which would turn him into a FallenHero.
40** ''Literature/GravePeril'': Harry deduces from the attack on [[spoiler:Charity and the baby]] that the Nightmare is being manipulated, as it’s a demon, and demons are absolutely incapable of understanding what things like love even ''are''. [[spoiler: Therefore, there's no way it would know that RevengeByProxy would be what hurt Michael the most.]] Harry turns out to be [[spoiler: RightForTheWrongReasons. Yes, the Nightmare is being manipulated, but it's not the ghost of a demon like Harry expected, but rather the ghost of an EvilSorceror that Harry defeated earlier, who, as a human, could comprehend love. So it's Invoked, but not played straight.]]
41** ''Literature/ColdDays'': Mab explains her belief that Harry indoctrinated Molly into serving him: he protected her at great personal risk and indebted her to him by providing help. The reader -- having had a close-up view of Harry's motivations -- knows that she's wrong: he did the above because he's a good person who didn't want Molly to suffer.
42** ''Literature/SkinGame'': [[spoiler: Hannah]]'s prejudice against the White Council (and presumably [[spoiler: Lasciel]]'s manipulation) means that they never get that Harry's offers of mercy and warnings that they're going down a dark path are genuine, and Harry really sympathizes with them and wants to help.
43** In a long scope view, this is Nicodemus' continual failure. While he might comprehend the factual idea a person can sacrifice one's self for another, his pride prevents him from understanding the most basic emotions behind this.
44*** ''Literature/DeathMasks'': At the end, he correctly guesses [[spoiler:Harry would grab a Coin of the Fallen to save a child from being infected by the Shadow of the Fallen. He fails to consider even remotely that Harry could and eventually does resist the Shadow to the point the Shadow is no longer the same entity she was when she first entered Harry's mind. Further more, she is so changed by Harry's resistance, she ends up sacrificing herself to save Harry out of love]].
45*** In ''Literature/SkinGame'' Nicodemus has laid a beat down on Harry and an ally, when a retired Knight is offering to take the place of both of them. [[spoiler:Archangel Uriel then appears and pleads with Michael to not make this sacrifice, but these people, like Uriel, are Michael's friends and they’re in need. Nicodemus laughs at Uriel and knows God Forbids Uriel from messing with Free Will, and so cannot simply smite Nicodemus (even when he flicks the Archangel). But Uriel is wiser and has more Faith than Nicodemus ever considers. As Michael has made the willing Choice to walk out and face Nicodemus, Uriel makes one of the only choices remaining to him: he temporarily gifts his Grace of God to this crippled man. The Grace heals Michael back to his prime but at a potential cost. Should Michael act in an evil manner, he will taint the Grace and cause Uriel to Fall. Nicodemus and his Fallen comrade are shocked beyond words at this action and agree to retreat for now]].
46* ''Literature/EastOfEden'': [[EmptyShell Cathy Ames]] is a sociopath whose only trait is to manipulate and hurt others for personal gain. When she runs away from home as a teenager, her parents note that her room has no personal possessions in it, and looks like no one has lived there. [[spoiler:But when she meets her son Cal for the first time, goodness makes her uncomfortable. Cathy eventually comes to realize that there's ''something'' she doesn't have (i.e. the ability to feel love) that others have, [[WhatIsThisThingYouCallLove but still doesn't know what it is]]]].
47* ''Literature/{{Empire of the East}}'': This is a chronic failing of the villains. The rulers of the eponymous [[TheEmpire Empire]] at one point attempt to bribe [[BigGood Ardneh]] into joining their side, not really understanding that there could be a being who just had no interest in the kind of power that they were offering. That being said, this trope is zig-zagged at least a little, in that at least some of them do get an inkling that Ardneh is just not like them, and has no interest in dominating anyone. They don't really understand him, but they do get that he is different from them.
48* ''Literature/TheFairyGodmother'': Prince Alexander is hunting when he comes across a knight preparing to rape a peasant girl, and the knight offers to share her with Alexander. Alexander is less than pleased. [[spoiler:It's an Elven illusion and the final test of Alexander's redemption.]]
49* ''The First Wives Club'': The Club forms when a mutual friend commits suicide due to her husband Gil leaving her for another woman. They target Gil in particular, but each of the various ex-husbands have the problem of not grasping how badly they treated their wives. The ladies end up ruining a major deal Gil set up that costs his partners several hundred million dollars. When a weakened Gil asks why they're doing this, they respond "ask Cynthia" and Gil is honestly baffled as to what his late ex has to do with this.
50** Gil had planned to buy up a Japanese company, then split it apart and sell it off. The girls informed the owner of this and the man thus refused to sell rather than put all his workers out of jobs. Gil's first reaction is to simply offer more money, not able to grasp someone would put the welfare of their workers over making a profit.
51* ''Literature/FoundationSeries'':
52** "Literature/TheGeneralFoundation": Privy Secretary Brodrig dismisses General Riose's (honest) claim to be devoted to the Imperium -- the only reason Brodrig can imagine for embarking on a war is to seize power for oneself. Devers confirms his belief, so he begins sucking up to Riose by getting him the reinforcements the general wants.
53** ''Literature/ForwardTheFoundation'': Joranum is baffled that Demerzel spends his time trying to keep the citizens of the provinces happy, when it's only on Trantor that a rebellion would be dangerous to Demerzel's power.
54* ''Literature/{{Freckles}}'': The villains first try to bribe Freckles to be slack in his watch.
55* ''Literature/GauntsGhosts'':
56** ''Only in Death'': [[spoiler: Soric]]'s [[EvilCripple keepers]] from [[FateWorseThanDeath the Black Ships]] think that he might kill Hark. (Hark, although he would not blame him if he did, knows that he is safe.)
57** ''Salvation's Reach'': Due to his one-sided grudge against Gaunt, Meryn just doesn't get the other man and thinks Gaunt's all about ceremony and favour. He could not be further from the truth.
58* ''Literature/GoblinsInTheCastle'': Well, not exactly "evil", but according to Granny Pinchbottom, the old Baron "didn't understand play, didn't believe in mischief, didn't know how to laugh." This is why he locked the goblins away -- because he couldn't understand their wild energy and thought they were evil, not realizing that they just liked to play and had been protecting the local children from danger and keeping the land productive, whereas the village now limps along every year without their help. Played straight with the evil sorcerer Ishmael[[note]][[DoNotCallMePaul Don't call him that!]][[/note]], who claims the goblins only caused "chaos", and that "Nothing could be settled, nothing could be quiet, nothing could be calm while they were around. It was like having too many children." He then calmly reveals the trickery he used to lure the goblins into a trap, to William's horror.
59* ''Literature/{{GONE}}'': Caine Soren seems genuinely puzzled in LIES as to why his female counterpart Diana Ladris doesn't want him to throw a helicopter full of children into a cliff.
60* ''Literature/TheGreatPacificWar'': The Japanese government makes this error. They've been interfering in China and supplying arms to rebellious warlords, and they see a US mining company winning a contract there as a front for the US government to interfere in China and supply arms to the government, even though no such thing is happening.
61* ''Literature/GreyKnights'': This is actually how the BigBad in the first book is defeated. His end appearance features him giving a long TheReasonYouSuckSpeech, stating that humanity has given up all the morals it previously held dear. He is ironically defeated by one which no daemon has ever understood: [[spoiler: willing self sacrifice. With a brilliant Interrogator giving up her life, sanity, and soul in order to learn the daemon's true name so it can be banished.]]
62* ''Literature/HarryPotter'': It’s repeatedly and explicitly demonstrated that Voldemort's inability to feel genuine love for anyone other than himself is his FatalFlaw.
63** ''Literature/HarryPotterAndThePhilosophersStone'':
64*** Professor Quirrell - who’s sharing his body with the currently non-corporeal Voldemort - sums up the Dark wizard's philosophy with the chilling line, “There is no good and evil; there is only power and those too weak to seek it.”
65*** Although not discussed in detail (yet), Dumbledore tells Harry that his mother’s HeroicSacrifice created a lasting protection in him that prevented Voldemort from killing him as a baby. The intrinsic power of that love was the factor that Voldemort failed to account for, and caused his downfall.
66** ''Literature/HarryPotterAndTheChamberOfSecrets'': While [[GloryHound Gilderoy]] [[ItsAllAboutMe Lockhart]] has no connection to Voldermort, and arguably has no outright “evil” tendencies, he’s so narcissistic the thought never crossed his mind that [[HumbleHero Harry]] doesn't seek fame like he does. Indeed, if he had paid any attention during their interactions, he would have seen that Harry loathes being in the spotlight.
67** ''Literature/HarryPotterAndTheGobletOfFire'': While Voldemort is later shown to play this trope straight, his main agent in this book does not. As he tells Harry, "Decent people are so easy to manipulate." Although [[spoiler:Barty Crouch Jr.]] does have a moment. He assumes that Harry will ask everyone for Tournament help, but Harry sticks with just his closest friends. This forces the agent to play XanatosSpeedChess.
68** ''Literature/HarryPotterAndTheOrderOfThePhoenix'': Dumbledore and Snape suspect Voldemort has discovered Harry's ability to access his mind, and that he might attempt to do the same to Harry, or worse, possess him entirely. In the story’s climactic battle, Harry’s beloved godfather Sirius Black is killed and the grief makes Harry homicidally furious. Voldemort does eventually succeed in possessing Harry and the latter begs to be killed, but the thought of seeing Sirius again hurts Voldemort so much that his possession of Harry breaks--love and grief are like poison to him. [[HorrifyingTheHorror This all terrifies Voldemort so much that he immediately flees the scene and never tries to get into Harry's mind ever again]].
69** ''Literature/HarryPotterAndTheHalfBloodPrince'': In preparation for their ultimate showdown, Harry learns about Voldemort’s childhood and time at Hogwarts from Dumbledore. On a psychological level, this largely explains his inability to comprehend love: Conceived through an enchantment and abandoned by his father before he was even born, Voldemort’s mother died giving birth to him and he was raised in a grim Muggle orphanage. Having never experienced real love in his life, it’s always been inconceivable to Voldemort that anyone could be motivated to sacrifice for others purely out of feeling.
70*** This is contrasted with Harry who, [[NotSoSimilar despite growing up in strangely similar conditions, turned out as almost the complete opposite]]. As Dumbledore emphasizes, Harry’s childhood misery never made him unfeeling towards others or wore away his moral compass. From his first moments at Hogwarts, Harry was kind, open, and generous. He made friends for the first time in his life and felt genuine guilt when he was in the wrong (things that Voldemort has never been willing or able to do). Harry has also never been tempted to engage in the Dark Arts in any way, something Voldemort’s followers seem willing to do at the drop of a hat just to be associated with his charismatic presence and similar worldview.
71** ''Literature/HarryPotterAndTheDeathlyHallows'':
72*** In his search for the titular Hallows, Voldemort's inability to understand the true meaning of "master of death" stumps him. He thinks it means immortality because he cannot see the world beyond himself. Harry [[HeroicSacrifice demonstrates that it is accepting the inevitability of one’s own death]] [[FaceDeathWithDignity and willingly walking towards it without fear]]. [[spoiler:Ironically enough, this course of action ends with [[LaserGuidedKarma Harry's resurrection]] and Voldemort's KarmicDeath]].
73*** Voldemort also plays with this during the Battle of Hogwarts by challenging Harry to turn himself in, claiming that he will spare the other students ([[WhatMeasureIsANonSuper or the pure-bloods, at least]]) if he does so. [[spoiler:By all appearances the ploy is successful, with Voldemort and his followers celebrating Harry’s death, but Harry is just playing possum to gain the advantage.]] As Harry points out, however, with this move, Voldemort repeated the exact same mistake he made the night he killed Harry’s parents: [[spoiler: forgetting the power inherent in a HeroicSacrifice.]] Inherent in the challenge is Voldemort’s assumption that Harry is using everyone around him as protection. It is incomprehensible to him that Harry's friends are fighting and dying of their own free will to protect someone else. Voldemort may understand intellectually that he can leverage someone by threatening those they care for, but he’s never understood the emotion behind ''why'' someone would behave selflessly.
74** It's not just Voldemort who cannot comprehend goodness. His {{mooks}} often display similar tendencies, albeit on a smaller scale.
75*** Two of his followers betray him out of love for another: [[spoiler:Snape becomes Dumbledore’s inside man because Voldemort killed Lily, and Narcissa Malfoy withholds key information from Voldemort to protect her son]], and his most faithful lieutenant Bellatrix Lestrange underestimates the power of love to strengthen Molly Weasley's resolve[[spoiler:, which ultimately leads to the Weasley matriarch taking Bellatrix down]].
76---->'''[[spoiler:Molly]]''': [[MamaBear Not my daughter, you bitch]]!
77* Various bad guys in the Literature/HonorHarrington universe consistently don't realize two things about the heroes in the setting: either they assume that good guys won't go out of their way to help others if they don't have to, and when they do act in a benevolent manner the bad guys think that they can be intimidated into backing down. One major part of the backstory in the books set in the Talbott Cluster is based on this misunderstanding. TheConspiracy is trying to make the Manticorans look bad by fomenting rebellions on planets in a FalseFlagOperation pretending to be Manticoran agents and assuring the rebels they'll have backing, setting them up to be crushed and giving the Manticorans a bad reputation. The plan assumes that if the Manticorans find out, they will refuse to get dragged into someone else's problems, especially if it puts them at odds with the Solarians, making their reputation worse. [[ScrewTheRulesImDoingWhatsRight When the Manticorans do intervene]], the local oppressors assume that by threatening to kill their own citizens unless the Manticorans leave will make them back off. Aivars Terekhov corrects this misconception with kinetic weapons strikes.
78-->'''Terekhov:''' [[GoodIsNotSoft Why is it that people like you always think you're more ruthless than people like me?]]
79** A lot of Manticore's nastier aristocrats (especially [[RoyalBrat Pavel Young]] and [[EvilChancellor Baron High Ridge]]) automatically assume that everyone is as ambitious, petty, greedy and morally bankrupt as they are, and therefore just about anything involving actual honor, loyalty or moral courage tends to [[SpannerInTheWorks trip them up.]]
80** In particular, Pavel thinks that Honor and her cronies have some demented vendetta against him, because she successfully hurt him once and enjoyed the feeling. What he can't understand is that ''he's'' the one with a vendetta, and it's so nasty that his destruction becomes a a matter of necessity.
81*** Whenever Pavel's attempts at derailing Honor's career are twarted by high-ranked naval officers, he immediately assumes Honor must be sleeping with them. He simply cannot think of any other reason why these important men would defy him and support a low-born nobody, and certainly not because they simply realized that Honor is very competent.
82*** On the profesional level, when the Manticore fleet is being chased by and taking fire from a superior Haven fleet, and just before their fleet was intended to disperse to minimize further losses, they detect the arrival of TheCavalry. Paval doesn't understand why the fleet commander won't order to disperse already, since the Haven fleet will soon spot the Manticore reinforcements and leave. Unlike Honor, he never even thinks that if the Haven fleet chases them a bit longer, they won't be able to avoid the Manticore reinforcements and can actually be defeated. He can only think in terms of his own personal safety.
83** Honor's detractors among the Manticoran nobility and military frequently assume she's a glory hound.
84* In ''Literature/{{Horns}}'' [[spoiler: Lee Tourneau]] is utterly confused by a single line in an email from a friend two weeks after his mother's death. The line? ''How are you holding up?'' In fact, he cannot fathom ''[[TheSociopath compassion, selflessness, or love.]]''
85* AM, the evil A.I. of ''Literature/IHaveNoMouthAndIMustScream'' is programmed unable to feel or create, but it does have creative thoughts of destruction and torture. Which it does, because it can't see humans as anything more than playthings who are utter bastards that deserve the punishments it gives them. This is expanded upon in the video game adaption.
86* ''Literature/InDeath'': This trope is used ''many'' times. Then again, a number of the villains can be placed in the category of TheSociopath. This causes them to make mistakes that lead to getting arrested or killed off.
87* In ''Literature/TheInterdependency'', Cardenia attempts to make peace with the Countess Nohamapetan by extending an olive branch: instead of executing her daughter for treason, Nadashe would be confined to a LuxuryPrisonSuite. The Countess, noted for her ruthlessness, is unable to parse this as anything other than an attempt to hold Nadashe hostage for the Countess's good behaviour. [[spoiler:Later, in a moment of VillainousBreakdown at her conspiracy's catastrophic defeat, the Countess flips out and confesses to assassinating Cardenia's half-brother, the original heir to the throne, and seemingly expects Cardenia to view this as something she owes the Countess for, not understanding that Cardenia ''doesn't have'' the Countess's hunger for wealth and power and would frankly have preferred not to be emperox at all.]]
88* In Creator/SMStirling's ''Literature/IslandInTheSeaOfTime'' series, the otherwise smart and highly competent villain, William Walker, is caught off guard whenever somebody sacrifices their life to oppose him. He can't comprehend the act, or that being utterly callous and self-serving really offends people who can see through his charm. The scary subversion comes later when after surviving his defeat he never fails to try to understand the motivations and capacities of others.
89* ''Literature/JustRevenge'': Prandus had - during UsefulNotes/TheHolocaust - murdered Max Menuchen's entire family, from youngest to oldest, Max himself having survived by accident. He believes that Max is capable of doing the same to his family.
90* In ''Literature/KushielsLegacy'', the Mahrkagir serves an [[GodOfEvil evil]] [[TheAntiGod Anti-God]] but cannot be inducted into his priesthood, because he would be required to sacrifice someone he truly loves, and his [[FreudianExcuse horrific upbringing]] left him incapable of understanding anything but death and suffering.
91* A protagonist example, Weed from ''Literature/TheLegendaryMoonlightSculptor'' is completely incapable of understanding charity or good will.
92* In ''Literature/LesMiserables'', KnightTemplar Javert cannot understand why Jean Valjean, someone he views as a criminal [[AllCrimesAreEqual and therefore evil]], would save his life with nothing to gain. [[spoiler:Javert jumps off a bridge so as not to have to perform an evil act himself: either turning in the man who saved him or allowing a criminal to go free.]]
93* Creator/CSLewis:
94** ''Literature/TheChroniclesOfNarnia'':
95*** ''Literature/TheMagiciansNephew'': Jadis' mistake when she tries to tempt Diggory in the garden (yes, [[DoesThisRemindYouOfAnything this is supposed to remind you of something]]) is saying he could just leave Polly behind when he returns to Earth so no one will find out he stole the apple. Polly actually has her own way home, but the "very meanness of the suggestion" [[YourApprovalFillsMeWithShame makes Diggory realize Jadis isn't trying to help him or his mother]] and renders all her arguments moot to him.
96*** In ''Literature/TheLionTheWitchAndTheWardrobe'', Jadis mocks Aslan for [[spoiler:letting her kill him in Edmund's place. Just before she stabs him, she laughs about how it's a pointless sacrifice, as she'll just kill Edmund in the battle the next day.]] Aslan even tells this to Susan and Lucy, that the only reason the Witch didn't realize what would happen was because she didn't understand the true meaning of "sacrifice".
97** This is essentially the theme of ''Literature/TheScrewtapeLetters'':
98*** As the VillainProtagonist himself notes, an inherent problem demons have in their battle against God is that they fundamentally don't understand His motivation; the denizens of Hell believe that the whole concept of "love" is a cover story for something more selfish and nefarious. Hell even has a division of their research department dedicated to comprehending good. It's one of the [[FailureIsTheOnlyOption worst jobs to get in Hell]].
99*** The devils so fundamentally misunderstand good that they are often outright told by the loyal angels that if they could just understand love and what God meant by love, they would be able to reenter Heaven. "Aha! So if we understand love -- that lie God tells the little human vermin -- we can storm Heaven in conquest!" The thought that understanding God's concept of love might redeem them all is utterly incomprehensible to them. Presumably, the loyal angels want the devils to finally understand God's concept of love and reenter Heaven, their sins forgiven.
100*** Further on in the book, Lewis seems to suggest that this problem is rooted in the nature of what evil is, in that evil is fundamentally incapable of creatively ''existing'' without good.
101---->"He has filled His world full of pleasures. There are things for humans to do all day long without His minding in the least -- sleeping, washing, eating, drinking, making love, playing, praying, working. Everything has to be ''twisted'' before it's any use to us. We fight under cruel disadvantages. Nothing is naturally on our side."
102*** Screwtape himself may qualify as a [[SubvertedTrope subversion]]. In one letter, he informs Wormwood that God "really loves the little [human] vermin" and has their best interests at heart. It later emerges that Hell's police state has been reading his mail, and he conspicuously revises his earlier position to suit Hellish orthodoxy; whether he believes his rescinded story is doubtful.
103** Lewis asserts this straightforwardly, in his own voice, in ''Mere Christianity'': "Good people know about both good and evil: bad people do not know about either."
104* Comes up multiple times in ''Literature/MarketOfMonsters'':
105** "She'd never seen the sense in doing something you were afraid of. Your brain was smart -- it wouldn't send your fear signals without good cause." Nita, to her initial surprise and confusion, learns over the course of the series that, contrary to what she always believed, there are things more important and forces stronger than self-preservation. After much denial, she accepts she wants Kovit with her even though she no longer "needs" him, even if she doesn't understand why.
106** Henry seriously underestimates how attached Kovit is to Nita, admitting during their confrontation in Adair's store that he just doesn't get it. He truly couldn't fathom that Kovit would ever choose Nita over him, let alone how he'd react when he learned Henry planned to kill her... Henry clearly never once considered things would result the way they did when he threatened the girl he assumed was already Kovit's lover.
107** Nita also assumed the only reason Adair took her and Kovit in was because she had valuable information he could use. It turns out her "information" was all useless -- when he reveals he let them keep living in his shop because he felt sorry for her, she truly doesn't believe him.
108* ''Literature/MarvelsSpiderManHostileTakeover'': Bingham doesn't understand why Spider-Man cares for and protects people, rather than abusing his power to lord over and terrorize the city. He sees that as proof that Spider-Man in unworthy of his power.
109* This is how the [[BigBad Storm King]] is finally defeated in Creator/TadWilliams' ''Literature/MemorySorrowAndThorn'' series. He plans for every act of resistance the heroes could offer, up to and including a [[EvilIsNotAToy last minute betrayal]] by Pryrates, but is fatally weakened when [[spoiler:Simon, who, instead of trying to fight him, apologizes for all his suffering]].
110* This applies to Ruin in ''Franchise/{{Mistborn}}''. He is the sentient force of destruction and entropy, and only builds up one thing if he knows he can use it to destroy two or more other things later. He is literally incapable of understanding human love and emotion, that there is more to life than the chaos of death at the end, why anyone would create something and NOT seek to destroy it later, but see it grow instead. This is used to [[spoiler:Destroy him in the end, when his unwilling servant kills Elend, causing Vin to sacrifice herself, using Preservation's power (Ruin's counterpart), to destroy him, (which Preservation was literally incapable of doing, so he created humanity to do so for him).]]
111* In his [[AlternativeCharacterInterpretation far from unbiased]] biography of General Moreau, Frédéric Hulot explains that Napoleon's far-reaching vendetta against Moreau stems from the fact that the selfish and ambitious Corsican could not understand why a man of Moreau's talents and influence would selflessly serve the Republic without seeking political power or personal gain.
112* ''Literature/MoribitoIIGuardianOfTheDarkness'': Yuguro doesn't understand selflessness, compassion, or love, considering his deceased brother, Jiguro, a pathetic fool for sacrificing everything he had -- his family, his friends, and his prestige -- for young Balsa, who, in his words, was "someone else's daughter."
113* ''Literature/MythAdventures'': It's selfishness rather than evil, but in ''Myth-ing Persons'' Skeeve tries to convince a woman he's attracted to that she doesn't need to stick with her con-artist partner now that he's out of trouble. She has no idea what he means; being in trouble is a reason she'd ''leave'' someone, not a reason she'd stick with them.
114* In Aaron Dembski-Bowden's Literature/NightLords novel ''Soul Hunter'', at the end, when [[spoiler:Ruven]] is pondering how to seize power, Talos seizes the chance for {{Revenge}} for his murder -- of a [[NiceToTheWaiter mere mortal, Talos's servant]]. To humiliate him, he explicitly says he looks, dying, as that servant's death had looked.
115** A similar (non-murderous) exchange passes between Talos and Variel. After betraying the Red Corsairs and joining the Night Lords, Talos assumes that Variel does so out of some debt owed him from long ago. When it seems likely that the two of them are going to die in their next mission, Talos offers to 'release' Variel from his debt, to which Variel acts with outrage. It never occurs to Talos, despite all they have been through together, that Variel considers them to be friends and not just an obligation.
116* In Creator/SeananMcGuire's ''Literature/OctoberDaye'' novel ''Ashes Of Honor'', Samson derides Toby as a sentimental fool and sneers at Tybalt for involving himself with someone so weak.
117* A gem from ''Literature/TheOnceAndFutureKing'': "Mordred and Agravaine thought Arthur hypocritical -- as all decent men must be, if you assume that decency can’t exist."
118* In ''Literature/PresidentsVampire'', Wayman can't understand why Griff, who's dying of cancer, won't use the Elixir of Life (made of HumanResources and created by a [[{{Ghostapo}} Nazi]]) to save himself. When Griffin tells him that there are some values you'd never sell for anything, he's even more baffled.
119* In ''Literature/ThePrincessDiaries: Royal Crush'', Luisa tries to spoil Olivia's happiness over becoming an aunt by scoffing that Olivia is just a SpareToTheThrone now. Olivia, who cares about family far more than power, is untouched by this jab.
120* In L. Jagi Lamplighter's ''[[Literature/ProsperosDaughter Prospero In Hell]]'', the reason offered for why the devils tried to frame Cornelius instead of one of her other brothers, which Miranda might have believed.
121* [[OurDemonsAreDifferent The demons]] of ''Literature/TheRiftwarCycle'' are destructive, chaotic beings that don't understand anything except for [[AmbitionIsEvil ambition]], [[HorrorHunger hunger]], and desire. The [[DemonLordsAndArchdevils Demon King]] [[TheChessmaster Dahun]] attempts to foster order, love, and loyalty among his followers in order to make them more efficient, but he ultimately fails because, as one character points out, he understood from observing humans that such things were important, but never ''why'' they were important. Child/[[spoiler: Miranda]], a demon with a human soul, ''does'' comprehend good, but is fully aware of her unique nature and the incogruity of a demon being [[spoiler: geniunely in love with the family of the human said soul originally belonged to]], though the end of the last book indicates that [[spoiler: she's going to return to Hell and ram love and empathy down the throats of the rest of her race whether they want it or not]].
122* ''Literature/RomanceOfTheThreeKingdoms'' has the situation surrounding the demise of the famed [[SuperDoc Hua Tuo]], as a case of "Suspicious cannot comprehend Selfless." Cao Cao ordered Hua Tuo to treat his headaches (modern scholars suggest the cause to be a brain tumor), and after his diagnosis Hua Tuo responded that he could treat the headaches with a grueling procedure involving cutting open the head, removing the malicious tissue, and closing the wound. Though this sounds gruesome, it is in fact a primitive yet accurate description of brain surgery. Having been the subject of assassination attempts before and being renowed for his own shrewd and ruthless opportunism, Cao Cao proved to be incredibly untrusting of people around him. Instead of accepting the medical treatment as a dangerous but honest attempt to save his life, he instead assumed this was Hua Tuo trying to kill him in the guise of a medical procedure and had the divine surgeon executed in a fit of anger. Cao Cao's rash decision and inability to understand the altruistic nature of a medical man [[LaserGuidedKarma would come back to bite him in the ass]]. Having executed the finest doctor in the land, Cao Cao later had to watch his beloved son Cao Chong die of illnesses that no one else could cure, and would eventually pass from his own untreated tumors.
123* In ''[[Literature/ShadowsOfTheApt Salute the Dark]]'', the Dragonflies are [[IGaveMyWord honor bound]] not to try to reclaim their lands. Stenwold points out that if they gather their armies as if they intended to reclaim them, the Wasps will assume they are not thus bound.
124* In the ''Franchise/SherlockHolmes vs [[Franchise/CthulhuMythos Cthulhu]]'' novels by Lois H. Gresh, chapters written by Professor Moriarty assume that the only reason Holmes opposes him is to prove his (in Moriarty's mind, supposed) intellectual superiority, and the archvillain's genius struggles mightily to understand actions that suggest Holmes ''doesn't'' see ordinary people as mere tools -- until he finds an explanation that "proves" to his own satisfaction that the detective's true motives are as selfish as his own.
125* ''Literature/TheSilerianTrilogy'': Kiloran seems genuinely baffled that Baran harbors such a grudge against him over abducting and raping his wife.
126* ''Literature/StarTrekNovelverse'':
127** Overseer Biron, a recurring villain in the ''Literature/StarfleetCorpsOfEngineers'' stories, doesn't understand the [[Franchise/StarTrek Federation]] or its Starfleet heroes, in particular their compassion. Why Starfleet officers and captains expend valuable resources helping non-essential crewmen or those of lesser station is beyond his comprehension. Biron is a highly intelligent being, but a product of a brutal and calculating culture that assigns worth to people based only on how productive and useful they are.
128** In the ''Literature/StarTrekTheLostEra'' novel ''Serpent Amongst the Ruins'', the Romulan Admiral Vokar thinks that the Algeron peace conference is a sign of weakness, and that the only reason it's happening at all is that the Romulan Star Empire and Federation are both uncertain whose side the Klingons will be on if it comes to war. And while he's deduced a fair amount of Harriman's plan by the end, he assumes the goal is to push the Klingons into allying with the Federation, rather than to push all three sides into making the peace work. The idea someone might want to avoid war ''even if they think they'd win'' seems completely alien to him.
129* Franchise/StarWarsLegends:
130** In the ''Literature/RevengeOfTheSith'' novelisation, Count Dooku is revealed to be incapable of comprehending things like joy and friendship, translating them into things like jealousy, pride, spite, and so forth. Kind of a subversion, because Anakin eventually kills him by calling on something he ''does'' understand -- ''[[TheDarkSide rage]]''.
131** The Tarkin Doctrine[[note]]In the Legends continuity, Tarkin's line "Fear will keep the local systems in line" is not just a personal opinion but a matter of Imperial policy.[[/note]] is basically the idea that "Fear of force > force itself", but in practice tends to run towards "Fear is the ultimate weapon", as embodied by deliberately oversized ships, especially [[ThatsNoMoon the Death Stars]]. Both sides of this equation fail miserably -- the moon-sized Death Stars get blown up by ships less than 35 meters long (an X-wing and the ''Millennium Falcon''), and the main thing about heroism is that it tends to involve courage, the ''refusal to give in to fear''. Essentially, the Tarkin Doctrine is a refusal to understand your opponents turned into a tactical philosophy, with all the success you'd expect.
132** To rub further salt into the Doctrine's wounds, Tarkin's main attempt to employ it -- [[KickTheDog the tactically unnecessary]] [[MoralEventHorizon destruction of Alderaan]] -- ended up neatly shooting itself (and by extension, TheEmpire) in the foot by causing Palpatine's approval rating [[ZeroPercentApprovalRating to slip ever closer to zero]], prompting the mass defection of nearly all of the Empire's Alderaanian officers, and providing massive sympathy for the Rebellion.
133** Almost all of the weapons created following the Tarkin Doctrine meet the same fate, to the point where it's [[LampshadeHanging lampshaded]] by Han Solo during the Yuuzhan Vong war.
134** ''Literature/NewJediOrder'': In Yuuzhan Vong society, twin siblings always fight each other to the death BecauseDestinySaysSo; seeing ''two'' sets of twins on the opposing side cooperating -- Luke with Leia and Jaina with Jacen -- seriously confuses them. (Truthfully, [[Literature/LegacyOfTheForce they were right about Jaina and Jacen]], just a couple of decades early.)
135** This trope is also essentially what caused Literature/DarthBane's RuleOfTwo to fall apart, culminating in both Vader's redemption and the events after Caedus' death. Darth Bane created it with the full expectation of the Sith Master either killing the Apprentice if the apprentice fails him or [[YouHaveOutlivedYourUsefulness does not have any usefulness left]], or otherwise the apprentice [[TheStarscream offing his master]] when the opportunity presents itself and/or becoming strong enough to overpower the master. He obviously never anticipated that either of the two would actually redeem themselves to the light side of the Force and either abandon the Sith way or also sacrifice themselves to take down the Sith before they killed their loved ones. He really should have, since the Sith Lord whose holocron inspired him to create the Rule of Two in the first place, Darth Revan, ultimately renounced the Dark Side, and Bane knew this. And Darth Vader wasn't even the first time it happened: in ''Literature/DarthPlagueis'', we learn that Darth Gravid tried to pull a similar HeelFaceTurn about 500 years before the movies, and destroyed a ton of the Banite Siths' collected knowledge before [[HeelFaceDoorSlam he was stopped and killed by his apprentice Darth Gean]].
136** In ''Literature/LukeSkywalkerAndTheShadowsOfMindor'', the BigBad ''thinks'' he understands, and at least is aware of them, but he vastly underestimates their power. Throughout the book, he goes on at length about how his particular flavor of TheDarkSide is greater than any other aspect of the Force. When he puts Leia through a particularly horrible AndIMustScream until her defense breaks, the love she has for Han, even then, ''hurts'' him, and he's unable to get through it. In the final confrontation, a MindScrew-y sequence involving him being the ultimate black hole, he swallows Luke and angrily thinks that if any of the Jedi had ever even glimpsed the truth of the Dark, it would have snuffed their tiny minds like candles in a hurricane--
137--->'''Luke:''' ''Was my tiny mind snuffed? I must have missed that part.''
138** In ''Literature/StarWarsKenobi'', [[spoiler:Orrin Gault]], an embezzler and perpetrator of a MonsterProtectionRacket who's SlowlySlippingIntoEvil, is repeatedly warned by Ben to "Turn back now," and can't make heads or tails of the instruction, since Ben doesn't make any moves to expose or extort him, or do anything else that would profit from the situation.
139** Borsk Fey'lya is a Bothan, and political dirty tricks are a way of life for Bothans. Fey'lya fails to understand that Leia is doing what she thinks is good for the New Republic rather than what will gain her political advantage, because the latter is how he thinks.
140** ''Literature/JediAcademyTrilogy'': As a Sith Lord, Exar Kun wields enormous power even 4,000 years after his death, enough that he was even able to defeat Luke Skywalker. However, it never occurs to him that while he might be far stronger than an individual Jedi, a group of them in harmony with each other can cumulatively wield a power that far surpasses his, even if many of those Jedi are still little more than students. [[spoiler:This proves his undoing.]]
141** ''Literature/IJedi'': The ruthless Moff Tavira is certain that Luke Skywalker ordered the destruction of Carida because she can understand neither a willingness to forgo an ultimate weapon like the Sun Crusher, nor can she grasp mercy (let alone grace such as Kyp Durron was shown). [[spoiler:Corran {{exploit|edTrope}}s this tendency of hers later: he knows Tavira wouldn't dare let a superweapon like the Sun Crusher be destroyed and therefore also assumes this of the New Republic, so he uses the Force to make her imagine the Sun Crusher launching from the ''Errant Venture'' and ramming her Star Destroyer ''Invidious''. This scares her into retreating from an easily winnable fight, ruining her reputation among the SpacePirates she commands permanently.]]
142** ''Literature/TheHanSoloTrilogy'':
143*** Only a short while after hiring him, the t'landa Til priests think nothing of revealing to Han that Exultation and the entire religion built around it are a giant scam, and laughing at the stupidity of the pilgrims who have fallen for it. Admittedly they have no way of knowing that he's fallen in love with one of the pilgrims in the meantime, but it still says something about them that they can't imagine that anyone "strong minded" could be offended by the revelation.
144*** In a minor example, the female slaver who Bria encounters during her raid on the ''Helot's Shackle'' just cannot fathom the idea that Red Hand Squadron want to ''free'' slaves, not steal them for sale later. This gives Bria a distraction as the woman attempts to comprehend the idea, and she shoots her.
145* ''Literature/TheStormlightArchive'': ArcVillain Sadeas drives himself to distraction wondering why Dalinar would trade his priceless, treasured Shardblade for a squad of Sadeas' indentured CannonFodder soldiers. The fact that Dalinar genuinely wanted to free the squad in gratitude for [[IOweYouMyLife saving his and his men's lives]] never even occurs to Sadeas; he assumes it to be some sort of set-up.
146* The ''Literature/SwordOfTruth'' holds that the truth is objective and self-evident and anyone who doesn't understand is selfish, weak, or deluded. Most of the eleven books are spent foiling, saving, or converting those people, respectively.
147** According to Jagang, Richard is evil because he's evil.
148** An entire book is spent with Nicci holding Richard captive, trying to understand him.
149** Dealing with the people of Anderith is somewhere between this and RefugeInAudacity. You just have to act bigger than them, because they just don't understand compassion.
150** The Hakens are taught that this is true and that they're evil because their ancestors did evil, and that the Anders are good because they were victimized. It mixes with the most horrifying case of mass Stockholm syndrome ever on the Hakens' part.
151** In the finale, Richard decides that this is true of the Imperial Order because they don't want to understand.
152** Notably averted with Darken Rahl and the Sisters of the Dark. They understand how good people think and plan on it.
153** Notably averted with the D'Harans, especially the Mord-Sith; it's assumed that this is true, but as Richard, Kahlan, and Zedd get to know some D'Harans and the D'Harans get to know their new Lord Rahl, it turns out that most of the evil of the D'Harans was a reflection of their leader, and that most of them are just people. Not all, though.
154* In David Edding's ''Literature/TheTamuli'' trilogy, it is revealed that the EvilPlan of the guy who was behind the scenes in the ''The Elenium'' trilogy went belly up when one person did something he couldn't imagine happening: she gave the MacGuffin with ultimate power to someone else instead of keeping it herself.
155* In Creator/PoulAnderson's "Literature/TimeLag", Bors wonders why the people of Vaynamo do not seize the Alfavala land for their own use. (Though he tends more to MoralMyopia and MightMakesRight.)
156* ''Literature/TressOfTheEmeraldSea'': According to [[LemonyNarrator Hoid]], [[TheDragon Laggart]] was never shown any kindness or compassion is his life, and consequently believes everyone is just as selfish, ruthless, and cruel as he is. He genuinely can't comprehend the idea that some people are ''genuinely'' kind to others without any hidden motive. [[spoiler: When he realizes Tress is sparing his life, not out of CruelMercy or some kind of ploy, but because she's just a nice person, the realization sends him fleeing the room in terror]].
157* ''Literature/ToKillAMockingbird'':
158** None of the citizens can understand why a white man would not only father children with a black woman, but acknowledge them and live with her family. He has to pretend to be a drunk for them to accept it.
159** There's a straight example in Bob Ewell's response to Atticus's question about what he did when he saw his daughter supposedly having been beaten and raped. He says that there was no reason to call a doctor, as her wounds weren't anything permanent -- missing the point that ''she was hurt'', and ''he should have cared about her well being''.
160* ''Franchise/TolkiensLegendarium'':
161** ''Literature/TheLordOfTheRings'':
162*** Gandalf's plan to throw the Ring into Mount Doom hinges on Sauron being unable to understand his enemies. It's a running theme of the book: ''"Well, let folly be our cloak, a veil before the eyes of the Enemy... the only measure that he knows is desire, desire for power; and so he judges all hearts. Into his heart the thought will not enter that any will refuse it, that having the Ring we may seek to destroy it."'' This assessment proves correct, and Gandalf and Aragorn are thus able to bluff Sauron into concentrating his attention on Gondor, allowing Frodo and Sam to slip into Mordor undetected. And, indeed, the moment Frodo puts on the ring inside Mount Doom, making its location known, Sauron immediately realizes the depth of his own folly and how close his destruction is. (Of course, Sauron is also ''correct;'' Frodo fails, claims the Ring, and only Gollum acting as the SpannerInTheWorks saves Middle Earth.)
163*** Gollum also cannot comprehend that someone would destroy his Precious and cannot abide another claiming it. He turns on Frodo and Sam when their quest is revealed and is driven off. When Frodo claims it, Gollum attacks. However, Frodo can command him. Frodo had warned Gollum that he would force him to cast himself from a high place and into fire if he ever turns on Frodo. Gollum does so, going to the Fire and taking the Ring with him. It's heavily implied that this was Eru's (God's) plan for the Ring all this time.
164*** When Sam takes the Ring, it tries to tempt him with the power to rule all of Mordor, turning the ashen wasteland into a verdant garden under his control. Sam dismissed the whole idea as ridiculous, since he only wants a small garden to tend to with his own hands. Turning Mordor into a garden would require thousands of slaves, meaning that he'd do none of the work himself. The Ring, and, by extension, Sauron, can't comprehend why someone wouldn't want to rule the world.
165*** Sauron can't understand that the Captains of the West willingly are trying to draw his attention in a heroic sacrifice to prevent him from seeing Frodo and the danger of the Ring going to Mount Doom. He assumes Aragorn, or another leader, has claimed the Ring and sends all his forces out to stomp the men of the West. Had he understood them, he could have just closed all roads to Mount Doom and waited for the Ring to fall back in his hands.
166*** Grima Wormtongue and Saruman are each extremely bewildered by mercy shown them by their enemies, and Saruman sees Frodo with great respect (and all the more hate for it) after Frodo lets him go.
167** In ''Literature/TheSilmarillion'', Morgoth never expects the Valar to come to the aid of the Noldor because "for him that is pitiless, the deeds of pity are ever strange and beyond reckoning."
168* ''Literature/TreasureIsland'': Played straight with the ''Walrus'' pirate crew. Near the end of the book, Long John Silver even points out to Dr. Livesey when the latter contemplates checking up on the surviving pirates, "...these men down there, they couldn't keep their word... and, what's more, they couldn't believe as you could."
169* ''Literature/LaVitaNuova'': The first GriefSong for Beatrice claims anyone wicked enough to leave that perfect lady unmourned must lack the mind to even picture her.
170* In Creator/SandyMitchell's ''TabletopGame/{{Warhammer 40000}}'' novel ''[[TabletopGame/DarkHeresy Scourge the Heretic]]'', while Kyrlock and Elyra are [[TheInfiltration infiltrating]] a smuggling operation, a man [[AttemptedRape goes to rape]] a girl also waiting to be smuggled. Elyra objects, and not comprehending why, he offers to share. Kyrlock realizes this, says that Elyra wouldn't take him up on it, but [[FakeDefector he would]] -- which the man cannot believe would be false, so lets Kyrlock get close enough to brain him.
171* In ''Literature/WarriorCats'', Hawkfrost's plan to take over the Clans fails because he literally cannot understand why his brother would rather earn the position of Clan Leader than kill the current leader and take it.
172* In ''Literature/WhatTheHellDidIJustReadANovelOfCosmicHorror'' (the third book in the ''Literature/JohnDiesAtTheEnd'' series) this is a characteristic repeatedly displayed by the female [[TheMenInBlack NON Agent]]. Every possible action, interaction, and relationship she sees in the most cynical way possible, for example seeing a flawed but basically decent and caring relationship between characters as really being a case of one partner psychologically and emotionally manipulating the other. The shining example however, is her discussion with [[TheHeart Amy]] when they go through the PortalDoor. She takes Amy into an AlternateUniverse where a horrifying [[SyntheticPlague bio weapon]] that creates agonizing, debilitating illness (but does not kill, forcing governments to take care of anyone infected for the decades of their natural life still remaining and causing the collapse of society) had been used and, of course, gotten out of control and infected the entire world. The agent thinks that the fact people didn't immediately respond with QuarantineWithExtremePrejudice and kill off the infected to stop the spread shows that humanity is hampered by caring too much about each other to [[IDidWhatIHadToDo do what is necessary]] to survive. Amy is completely dumbfounded that someone can look around at the scene of carnage, say that someone designed a weapon that causes literal decades of endless misery for which there is no cure, intentionally used it against other people, and think that the lesson to take away is that people are too nice to each other and care too much. (Amy leaves it unsaid that if humanity's FatalFlaw was being too nice and caring too much, that weapon would have never been invented in the first place, let alone used.)
173* Creator/MadeleineLEngle uses the quote above in ''Literature/AWrinkleInTime'', and it helps Meg Murray save Charles Wallace. [[spoiler:She realizes that the only thing she has which IT does not have is love. She [[PowerOfLove focuses on loving her little brother so much]] that IT is driven out in a CareBearStare of --]] hold on, [[SandInMyEyes got something in my eye...]]
174* In ''Literature/WyldersHand'', the narrator contrasts the lawyer, Josiah Larkin, a ChurchgoingVillain, with one of his clients, a genuinely moral and spiritual man:
175-->These frank people are a sore puzzle to gentlemen of Lawyer Larkin's quaint and sagacious turn of mind. They can't believe that anybody ever speaks quite the truth: when they hear it -- they don't recognise it, and they wonder what the speaker is driving at. The best method of hiding your opinion or your motives from such men, is to tell it to them.
176* In ''[[Literature/{{Xanth}} A Spell for Chameleon]]'', Trent hands over his sword to Bink so he will be armed while he keeps watch and [[KillMeNowOrForeverStayYourHand goes to sleep]]. Bink and Chameleon reason that Trent, despite the title "Evil Magician Trent", must be trustworthy because he is willing to trust them; an untrustworthy man would not have believed someone else to be trustworthy. (It's not the only evidence in his favor, but it's a strong piece of it.)
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