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* The murderous rogue AI of ''Literature/TheIlluminaeFiles'', AIDAN, first takes notice of [[TheHero Kady]] because of her prodigious hacking skills. He quickly starts thinking she's beautiful, envying her LoveInterest, and wishing he had a body so he could hold her. Despite how monstrous he is, his feelings for her are genuine enough to humanize him, and [[spoiler:Kady grows to care deeply for him after their EnemyMine, but whether she feels anything romantic is never revealed.]]

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* The murderous rogue AI of ''Literature/TheIlluminaeFiles'', AIDAN, first takes notice of [[TheHero Kady]] because of her prodigious hacking skills. He quickly starts thinking she's beautiful, envying her LoveInterest, {{Love Interest|s}}, and wishing he had a body so he could hold her. Despite how monstrous he is, his feelings for her are genuine enough to humanize him, and [[spoiler:Kady grows to care deeply for him after their EnemyMine, but whether she feels anything romantic is never revealed.]]
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Stockholm Syndrome was made a Useful Note due to cleanup.


* The Phantom's obsessive infatuation with Christine in ''Literature/ThePhantomOfTheOpera''. Leads to StockholmSyndrome on Christine's side and ends with IWantMyBelovedToBeHappy on the Phantom's side. The narrator pities him more than condemns him.

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* The Phantom's obsessive infatuation with Christine in ''Literature/ThePhantomOfTheOpera''. Leads to StockholmSyndrome UsefulNotes/StockholmSyndrome on Christine's side and ends with IWantMyBelovedToBeHappy on the Phantom's side. The narrator pities him more than condemns him.
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* In ''Literature/NoExit'', main villain [[spoiler: Ashley Garver]]develops a twisted infatuation for the female protagonist the more she fights back against him; he fantasizes about making her his girlfriend and marrying her in another life, but is still going forward with the plan of killing her as she would be a witness to his crimes.
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* In '' literature/ No exit'', main villain [[ spoiler: Ashley Garver ]]develops a twisted infatuation for the female protagonist the more she fights back against him; he fantasizes about making her his girlfriend and marrying her in another life, but is still going forward with the plan of killing her as she would be a witness to his crimes.

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* In '' literature/ No exit'', ''Literature/NoExit'', main villain [[ spoiler: [[spoiler: Ashley Garver ]]develops Garver]]develops a twisted infatuation for the female protagonist the more she fights back against him; he fantasizes about making her his girlfriend and marrying her in another life, but is still going forward with the plan of killing her as she would be a witness to his crimes.
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** In the book 'No exit', main villain Ashley Garver develops a twisted infatuation for the female protagonist the more she fights back against him; he fantasizes about making her his girlfriend and marrying her in another life, but is still going forward with the plan of killing her as she would be a witness to his crimes.

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** * In the book 'No exit', '' literature/ No exit'', main villain [[ spoiler: Ashley Garver develops ]]develops a twisted infatuation for the female protagonist the more she fights back against him; he fantasizes about making her his girlfriend and marrying her in another life, but is still going forward with the plan of killing her as she would be a witness to his crimes.
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** In the book 'No exit', main villain Ashley Garver develops a twisted infatuation for the female protagonist the more she fights back against him; he fantasizes about making her his girlfriend and marrying her in another life, but is still going forward with the plan of killing her as she would be a witness to his crimes.
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* In ''LightNovel/AnotherNote'', Beyond Birthday both loathes and loves his senpai, L, and [[IJustWantToBeYou begins to imitate the latter's looks and mannerisms]].

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* In ''LightNovel/AnotherNote'', ''Literature/AnotherNote'', Beyond Birthday both loathes and loves his senpai, L, and [[IJustWantToBeYou begins to imitate the latter's looks and mannerisms]].
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* The dictator [[DirtyOldMan Paulo Orlovsky]] from ''[[VideoGame/GadgetPastAsFuture The Third Force]]'' has been lusting after the protagonist, Elena Hausmann, ever since she was a child, and even after she soundly rejected his marriage proposal and he tore her dream of becoming a scientist away from her, his obsession is still so strong that he spends more time fantasizing about her than running his Empire. Years later, when Elena pretends to finally be warming up to Orlovsky while working for the rebellion against the Empire, she's able to easily fool him into thinking his "love" could be a two-way street.
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* In several of Creator/AgathaChristie's novels, the murderer falls in love with one of the heroic main characters, and this is presented as a humanising trait (though not to the level of MoralityPet or LoveRedeems). Examples include [[spoiler:Major Knighton for Katherine Grey]] in ''Literature/TheMysteryOfTheBlueTrain'' and [[spoiler:Norman Gale for Jane Grey]] in ''Literature/DeathInTheClouds''.

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* In several of Creator/AgathaChristie's novels, the murderer falls in love with one of the heroic main characters, and this is presented as a humanising trait (though not to the level of MoralityPet or LoveRedeems). Examples include with examples including [[spoiler:Major Knighton for Katherine Grey]] in ''Literature/TheMysteryOfTheBlueTrain'' and [[spoiler:Norman Gale for Jane Grey]] in ''Literature/DeathInTheClouds''.
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* In several of Creator/AgathaChristie's novels, the murderer falls in love with one of the heroic main characters, and this is presented as a humanising trait (though not to the level of MoralityPet or LoveRedeems). Examples include [[spoiler:Major Knighton for Katherine Grey]] in ''Literature/TheMysteryOfTheBlueTrain'', [[spoiler:Norman Gale for Jane Grey]] in ''Literature/DeathInTheClouds''.

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* In several of Creator/AgathaChristie's novels, the murderer falls in love with one of the heroic main characters, and this is presented as a humanising trait (though not to the level of MoralityPet or LoveRedeems). Examples include [[spoiler:Major Knighton for Katherine Grey]] in ''Literature/TheMysteryOfTheBlueTrain'', ''Literature/TheMysteryOfTheBlueTrain'' and [[spoiler:Norman Gale for Jane Grey]] in ''Literature/DeathInTheClouds''.
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* In several of Creator/AgathaChristie's novels, the murderer falls in love with one of the heroic main characters, and this is presented as a humanising trait (though not to the level of MoralityPet or LoveRedeems). Examples include [[spoiler:Major Knighton for Katherine Grey]] in ''Literature/TheMysteryOfTheBlueTrain'', [[spoiler:Norman Gale for Jane Grey]] in ''Literature/DeathInTheClouds''.
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* ''Literature/{{Caraval}}'': Jacks is obsessed with Tella.

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** In ''[[Literature/JohnCarterOfMars Thuvia, Maid of Mars]]''. Carthoris is in love with the title character, who is also desired by the BigBad, Prince Astok of Dusar and the secondary villain, [[MasterOfIllusion Tario]].

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** ''Literature/JohnCarterOfMars'': In ''[[Literature/JohnCarterOfMars Thuvia, ''Thuvia, Maid of Mars]]''. Mars'', Carthoris is in love with the title character, who is also desired by the BigBad, Prince Astok of Dusar and the secondary villain, [[MasterOfIllusion Tario]].



* Billy "Boil" seems to have one on the titular heroine of the ''Literature/CatRoyal'' series of books, although how much of a villain he is varies from book to book.

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* ''Literature/CatRoyal'': Billy "Boil" seems to have one on the titular heroine of the ''Literature/CatRoyal'' series of books, heroine, although how much of a villain he is varies from book to book.book.
* ''Literature/TheFallOfGondolin'': Maeglin betrays the hidden city of Gondolin to the Dark Lord in exchange for the king's daughter, who he has been obsessed with for centuries, despite Idril hating him and marrying someone else.

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* ''Literature/BehindBlueEyes'' by Anna Mocikat: Metatron is obsessed with making Nephilim his lover as well as second in command. [[spoiler: This includes erasing her memories of those things that cause her to question his allegiance. It is because he used to be in love with her ''father.'']]



* ''Literature/BehindBlueEyes'' by Anna Mocikat: Metatron is obsessed with making Nephilim his lover as well as second in command. [[spoiler: This includes erasing her memories of those things that cause her to question his allegiance. It is because he used to be in love with her ''father.'']]
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* ''Literature/BehindBlueEyes'' by Anna Mocikat: Metatron is obsessed with making Nephilim his lover as well as second in command. This includes erasing her memories of those things that cause her to question his allegiance. [[spoiler: It is because he used to be in love with her ''father.'']]

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* ''Literature/BehindBlueEyes'' by Anna Mocikat: Metatron is obsessed with making Nephilim his lover as well as second in command. [[spoiler: This includes erasing her memories of those things that cause her to question his allegiance. [[spoiler: It is because he used to be in love with her ''father.'']]
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* ''Literature/BehindBlueEyes'' by Anna Mocikat: Metatron is obsessed with making Nephilim his lover as well as second in command. This includes erasing her memories of those things that cause her to question his allegiance. [[spoiler: It is because he used to be in love with her ''father.'']]
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* Oh my God, The Darkling for Alina in ''Literature/TheGrishaTrilogy''. More than half of their conversations could serve as the quote for the trope page.

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* Oh my God, The Darkling for Alina in ''Literature/TheGrishaTrilogy''. More than half of their conversations could serve as the quote for the trope page.
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** In ''Literature/WorldWithoutEnd'' Ralph Fitzgerald has been obsessed since his teens with Lady Philippa, the Countess of Shiring and older than him, a poor squire. He [[spoiler: murders his first wife]] as soon as she's widowed and forces her to marry him. But RealityEnsues as Ralph has now to live with a woman not so young anymore and who utterly despises him. The crush lasts as long as you'd expect.

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** In ''Literature/WorldWithoutEnd'' Ralph Fitzgerald has been obsessed since his teens with Lady Philippa, the Countess of Shiring and older than him, a poor squire. He [[spoiler: murders his first wife]] as soon as she's widowed and forces her to marry him. But RealityEnsues SurprisinglyRealisticOutcome as Ralph has now to live with a woman not so young anymore and who utterly despises him. The crush lasts as long as you'd expect.
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* The Firebird Trilogy has a few examples:
**The main one is Triadverse Theo for Marguerite. [[spoiler: When Triadverse Theo takes over the body of the main Theo from Marguerite's universe, he flirts with her and is the only one who calls her Meg. When he is discovered, he reveals that he didn't have a chance with the Marguerite from his universe and he thought he had a chance with this Marguerite. They become enemies, but Theo tries to convince Marguerite to join him and Triad, but she refuses each time. Later in the trilogy, he kills the Marguerite from the Egyptverse, and while he is strangling her with the main Marguerite in her body, he begs her to jump to another universe while crying because he didn't want to kill two Marguerites. He then sacrifices himself to kill his universe's Wyatt Conley to protect Marguerite.]]
**In some of the universes, Wyatt Conley is in love with Josie, Marguerite's older sister. [[spoiler: When Triadverse Josie dies and her soul is splintered into thousands of pieces, Wyatt plans on getting her back by destroying the universes she had traveled to, which will force her splintered pieces back to the Triadverse. He refuses to destroy any universe where he and Josie are happy, and Marguerite realizes that her Wyatt avoided her Josie because he didn't want to have a weakness.]]
**Mafiaverse Paul seems to feel something for Marguerite. [[spoiler: But he kidnapped her and then shot Theo in both of his kneecaps in cold blood, so obviously that was doomed from the start. The Marguerite from the Mafiaverse said that Mafiaverse Paul, who is in the Russian mob and is the son of its leader, keeps sending her emails, but naturally, she wants nothing to do with him.]]
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* Literature/TheWormOuroboros: Gro, Heming and Corinius fall for Mevrian. Unluckily for them all, she's also vowed to Artemis. But recognizing the honorable character and intentions of Gro and Heming Mevrian turns them down with courtesy as opposed to her scornful rejection of the brutish Corinius.

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* Literature/TheWormOuroboros: ''Literature/TheWormOuroboros'': Gro, Heming and Corinius fall for Mevrian. Unluckily for them all, she's also vowed to Artemis. But recognizing the honorable character and intentions of Gro and Heming Mevrian turns them down with courtesy as opposed to her scornful rejection of the brutish Corinius.
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* Creator/EdgarRiceBurroughs has a plenty:

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* Creator/EdgarRiceBurroughs has a plenty:



* Apparently Ken Follet's historical novels have always the bad guy falling for an heroic character:

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* Apparently Ken Follet's historical novels have always the bad guy falling for an a heroic character:



** In ''Literature/WorldWithoutEnd'' Ralph Fitzgerald has been obsessed since his teens with Lady Philippa , the Countess of Shiring and older than him, a poor squire. He [[spoiler: murders his first wife]] as soon as she's widowed and forces her to marry him. But RealityEnsues as Ralph has now to live with a woman not so young anymore and who utterly despise him. The crush lasts as long as you'd expect.

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** In ''Literature/WorldWithoutEnd'' Ralph Fitzgerald has been obsessed since his teens with Lady Philippa , Philippa, the Countess of Shiring and older than him, a poor squire. He [[spoiler: murders his first wife]] as soon as she's widowed and forces her to marry him. But RealityEnsues as Ralph has now to live with a woman not so young anymore and who utterly despise despises him. The crush lasts as long as you'd expect.



* Literature/TheWormOuroboros: Gro, Heming and Corinius fall for Mevrian. Unluckily for them all she's also vowed to Artemis. But recognizing the honorable character and intentions of Gro and Heming Mevrian turns them down with courtesy as opposed to her scornful rejection of the brutish Corinius.

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* Literature/TheWormOuroboros: Gro, Heming and Corinius fall for Mevrian. Unluckily for them all all, she's also vowed to Artemis. But recognizing the honorable character and intentions of Gro and Heming Mevrian turns them down with courtesy as opposed to her scornful rejection of the brutish Corinius.
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* [[TreacherousAdvisor Rune]] in ''Literature/DunctonWood'' is shown to lust after the main character Rebecca; as soon as she reaches breeding age he is not hesitant to seek her out and attempt to seduce her, but he is stopped by her father [[BigBad Mandrake]]. He remains obsessed with her throughout the book.
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* The murderous rogue AI of ''Literature/TheIlluminaeFiles'', AIDAN, first takes notice of [[TheHero Kady]] because of her prodigious hacking skills. He quickly starts thinking she's beautiful, envying her LoveInterest, and wishing he had a body so he could hold her. Despite how monstrous he is, his feelings for her are genuine enough to humanize him, and [[spoiler:Kady grows to care deeply for him after their EnemyMine, but whether she feels anything romantic is never revealed.]]
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* In ''Literature/MrStandfast'', the evil mastermind is revealed to have fallen in love with the same woman the hero has, which adds to the feeling that this time ItsPersonal and contributes to the villain's downfall.
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* ''Literature/{{Ivanhoe}}'' has [[BloodKnight Brian de Bois-Guilbert]] for Jewish hottie Rebecca and tries to play the AbductionIsLove card. Being a BadassDamsel, Rebecca successfully foils his AttemptedRape and gives him a well-deserved TheReasonYouSuckSpeech.

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* ''Literature/{{Ivanhoe}}'' has [[BloodKnight Brian de Bois-Guilbert]] for Jewish hottie Rebecca and tries to play the AbductionIsLove card. Being a BadassDamsel, DefiantCaptive, Rebecca successfully foils his AttemptedRape and gives him a well-deserved TheReasonYouSuckSpeech.
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The main page for Villainous Crush was becoming too long. Certain sections, like Literature, were removed from the main page and split into subpages.

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* Creator/EdgarRiceBurroughs has a plenty:
** In ''[[Literature/JohnCarterOfMars Thuvia, Maid of Mars]]''. Carthoris is in love with the title character, who is also desired by the BigBad, Prince Astok of Dusar and the secondary villain, [[MasterOfIllusion Tario]].
** ''Literature/AtTheEarthsCore'', in which Hooja the Sly One lusts after David Innes's beloved Dian the Beautiful.
** It seems standard for [[DudeMagnet Dejah Thoris]] to be a magnet for villains who are infatuated with her. In ''Warlord of Mars'', [[BigBadEnsemble all three main villains]] -- [[TheCaligula Salensus Oll]], [[SmugSnake Matai Shang]] and [[TheBrute Thurid]] -- [[WeAreStrugglingTogether fight over who gets to possess her as concubine]].
* The Phantom's obsessive infatuation with Christine in ''Literature/ThePhantomOfTheOpera''. Leads to StockholmSyndrome on Christine's side and ends with IWantMyBelovedToBeHappy on the Phantom's side. The narrator pities him more than condemns him.
* Apparently Ken Follet's historical novels have always the bad guy falling for an heroic character:
** William Hamleigh for Aliena in ''Literature/ThePillarsOfTheEarth'', which is a [[IHaveYouNowMyPretty bad new for her]] the day he [[spoiler: takes over her castle]]. He keeps lusting after her even as [[UnrequitedLoveLastsForever they're reaching old age]].
** In ''Literature/WorldWithoutEnd'' Ralph Fitzgerald has been obsessed since his teens with Lady Philippa , the Countess of Shiring and older than him, a poor squire. He [[spoiler: murders his first wife]] as soon as she's widowed and forces her to marry him. But RealityEnsues as Ralph has now to live with a woman not so young anymore and who utterly despise him. The crush lasts as long as you'd expect.
* Billy "Boil" seems to have one on the titular heroine of the ''Literature/CatRoyal'' series of books, although how much of a villain he is varies from book to book.
* Played with in ''Literature/ASongOfIceAndFire'' with [[MagnificentBastard Littlefinger's]] affection for his childhood friend Catelyn Stark, and later on [[spoiler: [[ReplacementGoldfish her daughter]] [[BreakTheCutie Sansa]].]] He was an [[UsedToBeASweetKid idealistic and rather adorable kid]] when he fell in love with Cat, but the ensuing [[TraumaCongaLine line of events]] that put an end to that matter led to his [[StartOfDarkness moral backsliding]] into a schemer and a scoundrel (or as much a scoundrel a prominent public figure can be). However, it never really ended his feelings towards those ladies, and much of his development came from the offense of falling for a lady who was above his social status.
* Burgo Fitzgerald for Glencora M'Cluskie and George for Alice Vavasor in Creator/AnthonyTrollope's ''Literature/CanYouForgiveHer''.
* In ''Literature/TheBalancedSword'' by Creator/RykESpoor, [[spoiler:Aran Condor]] has a crush on the heroine, Kyri Vantage, which is complicated by the fact that he's secretly a member of the criminal gang that murdered her father, mother, and brother.
* ''Franchise/HarryPotter'': [[spoiler: Snape]]'s unrequited love for Lily Evans. [[spoiler:Though it's somewhat debatable that he even counts as a villain, seeing as everything he's done in life after Lily's death was to protect her son, Harry Potter. Even if he [[JerkAss treated him like shit]] because of [[CrazyJealousGuy petty jealousy]] over him being the son of James, who was TheRival to him.]]
* In ''LightNovel/AnotherNote'', Beyond Birthday both loathes and loves his senpai, L, and [[IJustWantToBeYou begins to imitate the latter's looks and mannerisms]].
* Count Kalliovski has one for young, pretty, innocent Sidonie in ''Literature/TheRedNecklace'', though truthfully it's much more [[IHaveYouNowMyPretty lust]] than love.
* Oh my God, The Darkling for Alina in ''Literature/TheGrishaTrilogy''. More than half of their conversations could serve as the quote for the trope page.
* In ''Literature/CrimeAndPunishment'' Svidrigailov, the wealthy and depraved former employer Raskolnikov's sister Dunya has nurtured a passion for her since the day she lay foot in his house, and seeks to win her back through blackmail.
* ''Literature/{{Ivanhoe}}'' has [[BloodKnight Brian de Bois-Guilbert]] for Jewish hottie Rebecca and tries to play the AbductionIsLove card. Being a BadassDamsel, Rebecca successfully foils his AttemptedRape and gives him a well-deserved TheReasonYouSuckSpeech.
* ''Literature/TheHouseOfTheSpirits'': Rather surprisingly - but actually not so much for a GenreSavvy reader - [[BastardBastard Esteban García]] develops one for heroine [[PluckyGirl Alba]] while he holds her captive. Too bad that [[IgnoredEpiphany he slams her into the isolation cell after figuring this out]].
* Literature/TheWormOuroboros: Gro, Heming and Corinius fall for Mevrian. Unluckily for them all she's also vowed to Artemis. But recognizing the honorable character and intentions of Gro and Heming Mevrian turns them down with courtesy as opposed to her scornful rejection of the brutish Corinius.
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