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Villainous Crush / Literature

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  • Edgar Rice Burroughs has plenty:
  • The Phantom's obsessive infatuation with Christine in The Phantom of the Opera. Leads to Stockholm Syndrome on Christine's side and ends with I Want My Beloved to Be Happy 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 a heroic character:
    • William Hamleigh for Aliena in The Pillars of the Earth, which is a bad new for her the day he takes over her castle. He keeps lusting after her even as they're reaching old age.
    • In World Without End Ralph Fitzgerald has been obsessed since his teens with Lady Philippa, the Countess of Shiring and older than him, a poor squire. He murders his first wife as soon as she's widowed and forces her to marry him. But Surprisingly Realistic Outcome 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.
  • Cat Royal: Billy "Boil" seems to have one on the titular heroine, although how much of a villain he is varies from book to book.
  • The Fall of Gondolin: 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.
  • Played with in A Song of Ice and Fire with Littlefinger's affection for his childhood friend Catelyn Stark, and later on her daughter Sansa. He was an idealistic and rather adorable kid when he fell in love with Cat, but the ensuing line of events that put an end to that matter led to his 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.
  • Behind Blue Eyes 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. It is because he used to be in love with her father.
  • Burgo Fitzgerald for Glencora M'Cluskie and George for Alice Vavasor in Anthony Trollope's Can You Forgive Her?.
  • Rune in Duncton Wood 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 Mandrake. He remains obsessed with her throughout the book.
  • In The Balanced Sword by Ryk E. Spoor, 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.
  • Caraval: Jacks is obsessed with Tella.
  • Harry Potter: Snape's unrequited love for Lily Evans. 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 treated him like shit because of petty jealousy over him being the son of James, who was The Rival to him.
  • In Another Note, Beyond Birthday both loathes and loves his senpai, L, and begins to imitate the latter's looks and mannerisms.
  • Count Kalliovski has one for young, pretty, innocent Sidonie in The Red Necklace, though truthfully it's much more lust than love.
  • The Darkling for Alina in The Grisha Trilogy. More than half of their conversations could serve as the quote for the trope page.
  • In Crime and Punishment 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.
  • Ivanhoe has Brian de Bois-Guilbert for Jewish hottie Rebecca and tries to play the Abduction Is Love card. Being a Defiant Captive, Rebecca successfully foils his Attempted Rape and gives him a well-deserved "The Reason You Suck" Speech.
  • The House of the Spirits: Rather surprisingly - but actually not so much for a Genre Savvy reader - Esteban GarcĂ­a develops one for heroine Alba while he holds her captive. Too bad that he slams her into the isolation cell after figuring this out.
  • The Worm Ouroboros: 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.
  • In Mr. Standfast, 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 It's Personal and contributes to the villain's downfall.
  • The murderous rogue AI of The Illuminae Files, AIDAN, first takes notice of Kady because of her prodigious hacking skills. He quickly starts thinking she's beautiful, envying her Love Interest, 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 Kady grows to care deeply for him after their Enemy Mine, but whether she feels anything romantic is never revealed.
  • The Firebird Trilogy has a few examples:
    • The main one is Triadverse Theo for Marguerite. 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. 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. 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.
  • In several of Agatha Christie's novels, the murderer falls in love with one of the heroic main characters, with examples including Major Knighton for Katherine Grey in The Mystery of the Blue Train and Norman Gale for Jane Grey in Death in the Clouds.
  • The dictator Paulo Orlovsky from 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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