History VillainousCrush / FanWorks

[[AC:''Franchise/SpiderMan'']]
* ''Fanfic/UltimateSpiderWoman'': When teenage misfit Ronald Hilliard went to a party and saw Spider-Woman fighting to protect the partygoers from the psychopathic [[ArchEnemy Jack O'Lantern]], he became convinced that [[ItsAllAboutMe Spider-Woman was fighting specifically to protect him.]] When he sees people criticizing her in the media, he uses his trust fund to turn himself into [[PsychoElectro an electrically-charged monstrosity]] and starts murdering Spider-Woman's critics as a way of proving his "love" for her. Spider-Woman is horrified at what he's done and bluntly tells him so. This causes Ronald, now calling himself Supercharger, to go into full-on {{Yandere}} mode and try to kill Spider-Woman herself for "humiliating" him. Now, he's torn between his crush on her and his [[IfICantHaveYou obsession with killing her for "rejecting" him]].

* ''Fanfic/LastChildOfKrypton'': Kaworu -a HumanoidAbomination willing to wipe out mankind in the rewrite- is infatuated with Asuka (who detests him).

* In the Possession AU stories, most notably the ''Fanfic/OurEternityTogether'' series, Mystic is often the love interest of the primary antagonist, the Cursed God. However it's heavily implied that his feelings towards her are solely romantic, as he's talked about [[spoiler:he's drawn to her because of her purity and innocence]]. In a similar vein, Envy is this to [[spoiler:Calvin, the mannequin maker]], but those feelings seem to be more sensual than the former.

* In the ''Fanfic/MyHostageNotYours'' series, second BigBad [[spoiler:Iggins']] obsession with Gaz starts out as wanting revenge, but in the end it seems he's got a thing for her as well, judging by his jealousy of Zim and his actions after [[spoiler:he manages to brainwash Gaz into his slave]].

* ''Fanfic/JerkInSheepsClothing'': Henri [=LeRoi=] was created by [[https://archiveofourown.org/users/BroadwayCutie16 [=BroadwayCutie16=]]] specifically to fill this role to Marinette, who has had to deal with her rivals for Adrien being {{Ice Queen}}s at best and {{Sociopath}}s at worst, while Adrien’s “competition” all trek into cinnamon roll territory. Unlike Luka, Nino, Theo, or Nathanael, Henri [=LeRoi=] is a BitchInSheepsClothing who sees Marinette as a prize to be won and is willing to crush anyone who gets between him and what he wants. The worst part is, so far, he’s actually succeeding, as Marinette truly believes him to be the golden-hearted guy of her dreams.

* In ''Fanfic/{{Strings}}'', Tarrlok had a crush on Korra since he first met her.

* ''FanFic/TheApprenticeTheStudentAndTheCharlatan'' features Envy, who has a certain fascination with protagonist Nova Shine [[spoiler:that carries over from her time as Summer Blossom]].

* ''FanFic/{{crawlersout}}'': Apparently, Dark Lords all have a thing for Fem!Harry Potter.
** Prior to his death, Lord Voldemort was ''obsessed'' with Harry, and that fixation evidently ruined any hope of Harry having a romantic life in her own time. Harry is convinced he didn't want to ''date'' her, though, but considering her relationship with Tom, Voldemort's child self, it's likely she didn't notice the possibility of a sexual aspect to it.
** Gellert Grindelwald took interest in Harry after an acquaintance asked him to look into her. [[spoiler:After Harry survives the Killing Curse and saves his life]], however, that fascination turns into a full-blown obsession. Grindelwald can't keep her out of his head and becomes a StalkerWithACrush.

* ''FanFic/TheEquestrianWindMage'': During Season 2, it's revealed that Ahuizotl is in love with Daring Do, and keeps up his evil schemes just to have an excuse to keep running into her. [[spoiler: In a case of LoveRedeems, it leads to him having a HeelFaceTurn, after which he confesses his feelings to her. They end up as an OfficialCouple.]]
* In the ''WebVideo/EscapeTheNight'' Possession AU stories, most notably the ''Fanfic/OurEternityTogether'' series, Mystic is often the love interest of the primary antagonist, the Cursed God. However it's heavily implied that his feelings towards her are solely romantic, as he's talked about [[spoiler:he's drawn to her because of her purity and innocence]]. In a similar vein, Envy is this to [[spoiler:Calvin, the mannequin maker]], but those feelings seem to be more sensual than the former.
* ''[[Fanfic/AFutureOfFriendshipAHistoryOfHate A Future of Friendship, A History of Hate]]'': [[VillainWithGoodPublicity Megalos]] [[EvilPrince Tyrant]] -- one of [[BigBad Ruinate]]'s [[CoDragons heralds]] -- takes a(n obsessive) shine to Rarity, viewing her as the perfect mate to complete his "[[{{Narcissist}} perfect]]" lifestyle. As such, he[[spoiler:, in his [[BitchInSheepsClothing public]] [[SecretIdentity guise]] as [[PrinceCharming Regal Rule]], woos her and lures her away from her friends]] before trying to convince her to return to his kingdom and be his queen... and then [[AndNowYouMustMarryMe tries to abduct her when she refuses]]. And even though he's beaten, he swears [[WeWillMeetAgain to return for her]].
* The ''Anime/Danganronpa3'' fic ''[[http://archiveofourown.org/works/8027512?view_adult=true How Long]]'' interprets [[spoiler:Chisa]] as retaining affection for Kyosuke even after her FaceMonsterTurn...as much affection as a Remnant is capable of having, anyway. A lot of her manipulations are motivated by wanting to share the "wonderful bliss" of (D)espair with him.
* In the ''Manga/DeathNote'' fic ''Fanfic/IWontSay'' Light/Kira towards L. [[DatingCatwoman He decides even though L is Kira's enemy, there's no reason he still can't be his boyfriend]], especially since Light feels that he has already "won", having discovered L and Watari's [[IKnowYourTrueName true names]] and so [[HilarityEnsues he tries to persuade L that getting together would be the best thing for both of them.]] Though Light starts out kind of scary like a {{Yandere}}-ish StalkerWithACrush, a dose of LimaSyndrome later, he becomes more of a DoggedNiceGuy as he works to earn L's affections.
* In ''FanFic/ImperfectMetamorphosis'', [[HumanoidAbomination Yuuka]] has barely disguised lust towards Wriggle, and to a lesser extent the rest of Team 9. Predictably, Wriggle is horrified.
* Henri [=LeRoi=] from ''Fanfic/JerkInSheepsClothing'' was created by [[https://archiveofourown.org/users/BroadwayCutie16 [=BroadwayCutie16=]]] specifically to fill this role to Marinette, who has had to deal with her rivals for Adrien being {{Ice Queen}}s at best and {{Sociopath}}s at worst, while Adrien’s “competition” all trek into cinnamon roll territory. Unlike Luka, Nino, Theo, or Nathanael, Henri [=LeRoi=] is a BitchInSheepsClothing who sees Marinette as a prize to be won and is willing to crush anyone who gets between him and what he wants. The worst part is, so far, he’s actually succeeding, as Marinette truly believes him to be the golden-hearted guy of her dreams.
* In [[https://www.fanfiction.net/s/8602275/1/Lady-and-the-Tramp-III-Family-Troubles Lady and The Tramp III: Family Troubles]] Buster begins to fall in love with Lady and make her give up Tramp and be his, taking advantage of the fact that he had gone.

* ''FanFic/MegaManRecut'' has Snake Man having a crush on Roll, though he doesn't realize it.
* In the ''Manga/AttackOnTitan'' fanfic [[https://www.fanfiction.net/s/10156375/1/My-Child My Child]], the [[FauxAffablyEvil demon]] [[OriginalCharacter Xaphan]] appears to find Levi attractive, speaking to him suggestively and calling him [[TermsOfEndangerment "my dear" and "my darling"]]. More frighteningly, Levi's thoughts all but state that [[spoiler: once Xaphan took Levi's soul and dragged him to hell, he [[RapeIsASpecialKindOfEvil raped Levi]] [[NightmareFuel countless times]], among other tortures.]]
-->'''Xaphan''': Come now, we both know you don't mean it when you say you don't want me.
* In the ''FanFic/MyHostageNotYours'' series, second BigBad [[spoiler:Iggins']] obsession with Gaz starts out as wanting revenge, but in the end it seems he's got a thing for her as well, judging by his jealousy of Zim and his actions after [[spoiler:he manages to brainwash Gaz into his slave]].

* ''Film/TheSchoolForGoodAndEvil2022'' fanfic ''Fanfic/NotAPrince'': Lady Lesso is the Dean of the School for Evil and happily teaches students to be evil villains. However, she develops feelings for Professor Dovey, the Dean of the School for Good, who trains students to be heroic heroes of fairy tales.
* In ''Fanfic/OurTimeIsNow'', Eric's past feelings for Jerrica bubble up and worsen due to his VillainousBreakdown. This results in him [[spoiler:threatening to rape]] Jerrica after he [[spoiler:kidnaps her]]. When the police take him away, all Eric can say is that he did it all "for her". In his poor state of mind he similarly confesses his love to Pizzazz, who is just disgusted and unnerved by what has become of Eric.
* In the ''[[VideoGame.TeamFortress2 Team Fortress 2]]'' fic ''Paternal,'' Bane, a purple Spy working for the Administrator, holds a villainous lust for the BLU Scout, [[IHaveYouNowMyPretty tying him up and forcefully kissing him on multiple occasions.]]
* In ''Fanfic/PoniesReactionverse'', Queen Chrysalis believes she has fallen in love with [[Manga/{{Berserk}} Guts]]. She is impressed by his badass nature and brutal achievements, and the carnage he leaves against his enemies is [[AllGirlsWantBadBoys a major turn-on for her]].
* In the ''FanFic/PonyPOVSeries'', [[spoiler:Discord's sister]] Rancor develops a thing for [[BadFuture Dark World!]][[BadassBookworm Spike]], constantly flirting with him during her presence in that StoryArc (much to Rarity's annoyance, as she and Spike are an OfficialCouple by that point).
** Also in Dark World, [[EvilOverlord Discord]] seems to have developed feelings for Pinkie Pie, as after [[spoiler:her [[HeelFaceTurn redemption]]]], he actually proposes to her [[spoiler:to get her back on his side. She politely, but strongly, refuses.]]
* ''Fanfic/PredatorAndPrey'': Alejandro has one on Bridgette in this fic's interpretation of ''Total Drama World Tour'' - albeit in the manner of a sexual predator with a favourite victim. Unfortunately for Bridgette, she finds herself developing unwanted feelings for him despite knowing full well she should be loving Geoff.
* Quick Man develops a crush on Roller Brawl in ''Fanfic/RollerBrawlTheMegaCyborg'' after meeting her, and calls her flirtatious nicknames like "Roller Beauty" and "Roller Babe", even offering a kiss for luck when she and Mega Man go to fight Wood Man. [[spoiler: This later evolves into LoveRedeems when Quick Man makes a HeelFaceTurn and betrays Dr. Wily to help her get through his creator's fortress]].
* ''Fanfic/TheUltimateEvil'':
** [[WesternAnimation/JackieChanAdventures Shendu]] initially becomes interested in Valerie Payne due to her being [[SinsOfOurFathers a descendant of the wizard who originally turned him to stone]] as well as [[YinYangBomb his Other]]. In order to claim her both physically and in spirit, he attempts to seduce her to make her more compliant to him, and his feelings end up gradually turning from possessive to [[MoralityPet genuine care]]. Valerie is initially freaked out by this interest, but the animosity lessens over time as [[VillainousRescue he saves her life]] several times.
** Drago likes grossing out [[HunterOfMonsters Nataline "Nat" Homato]] in the sequel, but he eventually develops a real crush on her as the demon hunter grows more empathetic towards him during EnemyMine situations.
* The version of Mirror Kirk who features in ''[[Fanfic/StarTrekMirror Star Trek: Mirror]]'' has one of these on Spock, as he regards the Vulcan as his DoppelgangerReplacementLoveInterest. Unlike many examples of this trope, he never tries to force anything sexual to happen between the two of them and wants Spock to defect and join him of his own free will.
* In ''FanFic/{{Strings}}'', Tarrlok had a crush on Korra since he first met her.
* According to [[WesternAnimation/SheRaPrincessOfPower Light Hope]] the titular artifact in [[https://www.fanfiction.net/s/363684/1/The-Locket-of-Love Locket Of Love]] cannot spontaneously generate feelings of love and devotion, only intensify those that are already there. At the end, it is revealed that [[BrattyHalfPint Imp]] does indeed have unrequited feelings towards [[DefectorFromDecadence Adora]]. Funnily enough, this also indicates Shadow Weaver has a crush on Hordak, and Mantenna in turn for her.
* Vaati in ''Webcomic/ATaleOfTwoRulers'' has a crush on Zelda. He tries to hit on her, right before her wedding no less, but she just splashes alcohol in his face.
* ''FanFic/UltimateSpiderWoman'': When teenage misfit Ronald Hilliard went to a party and saw Spider-Woman fighting to protect the partygoers from the psychopathic [[ArchEnemy Jack O'Lantern]], he became convinced that [[ItsAllAboutMe Spider-Woman was fighting specifically to protect him.]] When he sees people criticizing her in the media, he uses his trust fund to turn himself into [[PsychoElectro an electrically-charged monstrosity]] and starts murdering Spider-Woman's critics as a way of proving his "love" for her. Spider-Woman is horrified at what he's done and bluntly tells him so. This causes Ronald, now calling himself Supercharger, to go into full-on {{Yandere}} mode and try to kill Spider-Woman herself for "humiliating" him. Now, he's torn between his crush on her and his [[IfICantHaveYou obsession with killing her for "rejecting" him.]]

* Quick Man develops a crush on Roller Brawl in ''Fanfic/RollerBrawlTheMegaCyborg'' after meeting her, and calls her flirtatious nicknames like "Roller Beauty" and "Roller Babe", even offering a kiss for luck when she and Mega Man go to fight Wood Man.

** Gellert Grindelwald took interest in Harry after an acquaintance asked him to look into her. [[spoiler:After Harry survives the Killing Curse and saves his life]], however, that fascination turns into a full-blown obsession. Grindelwald can't keep her out of his head, and becomes a StalkerWithACrush.

* Henri [=LeRoi=] from ''Fanfic/JerkInSheepsClothing'' was created by [[https://archiveofourown.org/users/BroadwayCutie16 [=BroadwayCutie16=]]] specifically to fill this role to Marinette, who has had to deal with her rivals for Adrien being {{Ice Queen}}s at best and {{Sociopath}}s at worst, while Adrien’s “competition” all trek into cinnamon roll territory. Unlike Luka, Nino, Theo or Nathanael, Henri [=LeRoi=] is a BitchInSheepsClothing who sees Marinette as a prize to be won and is willing to crush anyone who gets between him and what he wants. The worst part is, so far, he’s actually succeeding, as Marinette truly believes him to be the golden-hearted guy of her dreams.

--> '''Xaphan''': Come now, we both know you don't mean it when you say you don't want me.

* In ''Fanfic/PoniesReactionverse'', Queen Chrysalis believes she has fallen in love with [[Manga/{{Berserk}} Guts]]. She is impressed by his badass nature and brutal achievements, and the carnage he leaves against his enemies is [[AllGirlsWantBadBoys a major turn on for her]].

* The version of Mirror Kirk who features in ''[[Fanfic/StarTrekMirror Star Trek: Mirror]]'' has one of these on Spock, as he regards the Vulcan as his DoppelgangerReplacementLoveInterest. Unlike many examples of this trope, he never tries to force anything sexual to happen between the two of them, and wants Spock to defect and join him of his own free will.

* According to [[WesternAnimation/SheRaPrincessOfPower Light Hope]] the titular artifact in [[https://www.fanfiction.net/s/363684/1/The-Locket-of-Love Locket Of Love]] cannot spontaneously generate feelings of love and devotion, only intensify those that are already there. At the end it is revealed that [[BrattyHalfPint Imp]] does indeed have unrequited feelings towards [[DefectorFromDecadence Adora]]. Funnily enough, this also indicates Shadow Weaver has a crush on Hordak, and Mantenna in turn for her.

* ''FanFic/UltimateSpiderWoman'': When teenage misfit Ronald Hilliard went to a party and saw Spider-Woman fighting to protect the partygoers from the psychopathic [[ArchEnemy Jack O'Lantern]], he became convinced that [[ItsAllAboutMe Spider-Woman was fighting specifically to protect him.]] When he sees people criticizing her in the media, he uses his trust fund to turn himself into [[PsychoElectro an electrically-charged monstrosity]] and starts murdering Spider-Woman's critics as a way of proving his "love" for her. Spider-Woman is horrified at what he's done, and bluntly tells him so. This causes Ronald, now calling himself Supercharger, to go into full-on {{Yandere}} mode and trying to kill Spider-Woman herself for "humiliating" him. Now, he's torn between his crush on her and his [[IfICantHaveYou obsession with killing her for "rejecting" him.]]

* In ''Fanfic/TheUltimateEvil'', [[WesternAnimation/JackieChanAdventures Shendu]] develops this on [[OriginalCharacter Valerie]], both for being a descendant of his once intended bride 900 years earlier ''and'' for being his [[BalanceBetweenGoodAndEvil Other]]. He has made as one of his goals to have her both physically and in spirit, and over time his feelings towards her turn from possessive to [[MoralityPet genuine care]]. Valerie is initially freaked out due to this interest, but the animosity lessens over time with [[VillainousRescue him saving her life]] several times.