History Main / VillainousCrush

** A deleted scene has Scar trying to make Nala his queen by making sexual advances at her and cornering her, but she claws him into making him stop. He won't take no for an answer, so he declares to the pride that he chooses Nala to be his queen, but she rejects him. Scar then makes the pride banish her out of Pride Rock, but they refuse to do so. So he orders the hyenas to banish her themselves. This deleted scene was supposed to be a reprise of ''Be Prepared'', but it was used in the [[Theatre/TheLionKing Broadway version]] during the song, ''The Madness of King Scar''.

[[folder:Web Original]]
* In keeping with her role as sex goddess of TGWTG, WebVideo/AskThatGuyWithTheGlasses is implied to have a crush on Creator/AllisonPregler (not so much since he fired her IRL). He's also slept with AntiHero champion of the universe Linkara.

-->'''Light:''' Well, we've been outside talking for awhile and we've decided to make it official. '''''I LOVE L! AND HE LOVES ME!''''' I'm going to dump Misa so I can be with L!
-->'''Everyone:''' ''Gasp''
-->'''L:''' [[HilarityEnsues No, I think you've misinterpreted the situation..]].
* [[AntiVillain Dr. Horrible]], of ''WebVideo/DoctorHorriblesSingAlongBlog'', has a crush on a local do-gooder, but his arch-nemesis [[AntiHero hero]] beats him to the punch. Unusually, Dr. Horrible is more of a WellIntentionedExtremist, while the so-called hero is an [[SmugSuper arrogant bully]] who only dates the girl to make the protagonist jealous.

* ''WebVideo/ResidentEvilAbridged'': In a scene [[TheStinger after the credits]], Chris finds a document that turns out to be a fanfic written by his [[MoleInCharge traitorous captain, Wesker.]] He gets two pages in before it starts to get explicit, prompting Chris to draw his gun and shoot it [[{{Squick}} out of revulsion.]]
-->'''Chris:''' ''[horrified]'' Ugh! [[{{Yaoi}} THIS]] must be the [[StealthPun "resident evil!"]]

* ''Literature/{{Twig}}'': [[VillainProtagonist Sylvester's]] feelings gradually shifts from subtle, to finally admitting that he doesn't see a difference between admiring someone for their abilities and being romantically attracted to them. Meaning that, yes, he's been crushing on his recurring enemies Genevieve Fray and Reverend Mauer.
* WebVideo/ProZD: Parodied in [[https://www.youtube.com/watch?v=LdoiBdNeCbM failing to keep your crush on the down low around the other villains]]. The villain makes his sexual attraction extremely obvious, despite apparently trying to hide it.

* The Ice King in ''WesternAnimation/AdventureTime'' would be a very extreme case of this. Early on in the show, he was known for kidnapping numerous princesses and try to [[AndNowYouMustMarryMe force them to marry him]], with Princess Bubblegum being his main victim.
* ''WesternAnimation/AvatarTheLastAirbender'': [[PerkyFemaleMinion Ty Lee's]] one-sided crush on Sokka was an amicable example, since he was flattered by it in ''"The Drill"'' episode. Though he later tells her that he was already seeing Suki, in ''"The Crossroads of Destiny"''.

* On ''WesternAnimation/ElTigreTheAdventuresOfMannyRivera'', this trope is well-done.
** Manny has Zoe Aves AKA Black Cuervo. At first, she only seduced him to manipulate him into hurting Frida, whom she hates. But after he saw her true colors and defeated her, showing his ferocious side, [[UnrequitedLoveSwitcheroo the crushes were swapped]].
** Frida herself has Diego AKA Dr. Chipotle Jr. and Sergio AKA Senor Sinestro, who have turned on each other to compete for her affections, then teamed up to destroy Manny, who they saw as romantic competition. She also has Django of the Dead.
** Manny’s father, White Panthera, dated Voltura AKA Carmelita Aves, Zoe’s mom before he dumped her and went on to marry Maria. Years later, she’s still bitter over it.

** This happened to Mabel Pines twice, the first being Norman/Jeff [[spoiler:which turned out to actually be a colony of gnomes that [[AndNowYouMustMarryMe want her to be their queen by marrying all 1,000 of them]]]] and the creepy [[EnfantTerrible 9-going-on-10 year old]] PhonyPsychic Mystery Shack rival Gideon (who tends to lean more towards a StalkerWithACrush).
** Giffany might also count, but Soos ''did'' return her affection. That is, until she became a total {{Yandere}}.
* ''WesternAnimation/{{Grossology}}'': Both of Chester/Kid Rot's personalities have a fondness for Abby, though it's more pronounced with Kid Rot. For her part, Abby may have a thing for Chester, but loathes Kid Rot.
* ''WesternAnimation/HarveyBirdmanAttorneyAtLaw'' plays this for laughs twice:
** X's obsession with Harvey and getting his crest drifts into this territory as he's remained obsessed with Harvey ever since getting that assignment, despite the fact that Harvey has retired from superheroics and the organization that hired X to get his crest ''no longer exists''.
** Hero-villain relations is seen as a metaphor for sex in "Peanut Puberty" when Peanut achieves 'superty' and gets his powers. He gets advice from Black Vulcan, who describes his first time fighting a villain (which ends with [[SmokingHotSex them smoking cigarettes]] [[DoesThisRemindYouOfAnything together]]) and the episode ends with Peanut introducing his 'villain friend'.
* WesternAnimation/LooneyTunes. A 1935 Merrie Melodies short, ''[[https://www.youtube.com/watch?v=0cWTEwpGsc8 The Little Dutch Plate]]'' subverts it. The [[DastardlyWhiplash villainous]] Vinegar Bottle (all the characters are household items) who has been pursuing the Girl on the Little Dutch Plate gets in a fight with the hero (a little Dutch boy saltshaker), who literally knocks his block off (Vinegar's head is just a bottlestopper, after all). Looking for his head, he accidentally puts on a girlish one from a perfume bottle. The Girl sees his new PrettyBoy looks and immediately ''defends'' him from the Boy, walking off with him while cooing "You handsome man!"
* One time on ''WesternAnimation/TheSimpsons'' Marge got a job at the nuclear plant and Mr. Burns developed a thing for her. However, when he realised how much Homer and Marge were in love, he withdrew his jealous affections and instead [[PetTheDog let them go on the fancy date he had prepared for Marge and himself.]] With a captive Music/TomJones no less.
* The ''WesternAnimation/GIJoeARealAmericanHero'' episode "The Gamemaster" not only hints that Zartan has something like this towards Scarlett, but that she reciprocates it!
* In the "Super Powers Team" incarnation of ''WesternAnimation/{{Superfriends}}'', Darkseid had a crush on Franchise/WonderWoman and constantly tried to make her his bride.
* In one episode of ''WesternAnimation/TeenTitans2003'', Red X flirts with Starfire after pinning her to the wall with one of his gadgets, calling her "cutie" and remarking that the "only crime" between them is that they haven't gone on a date. (Her only response is to blast him with her starbolts through her eyes.)
* Pyro once tried making a pass at Rogue in ''WesternAnimation/XMenTheAnimatedSeries''. She replied by throwing him through the wall as a non-subtle "No".

** While we're talking about the Turtles, in ''WesternAnimation/TeenageMutantNinjaTurtles1987'', [[BigBad the Shredder]] seemed to have a thing for April. This gets parodied in a Robot Chicken sketch where they become full on StarCrossedLovers.
** One episode of the 80s TMNT 'toon, ''Green With Jealousy'' sees one of Shredder's henchmen Rocksteady develop a crush on April after eating a pizza laced with a love potion. He proceeds to kidnap her and plot out a wedding, even instructing his pal Bebop to swipe a ring and kidnap a preacher. The crush is entirely one-sided, though April at one point tries to openly flirt with Rocksteady in order to buy the Turtles time to rescue her.
* PlayedForLaughs on ''WesternAnimation/WordGirl,'' with [[GadgeteerGenius Tobey McCallister]]'s crush on the titular character. She almost always rebuffs him, but there are some cases of legitimate ShipTease between them.
* ''WesternAnimation/{{Grossology}}'': While Chester is already shown to have a thing for Abby, it's far more pronounced in his [[SuperpoweredEvilSide Kid Rot]] persona.
* ''WesternAnimation/{{Kaeloo}}'': The main antagonist of the show, Mr. Cat, has a massive crush on the protagonist, Kaeloo; [[ObliviousToLove Kaeloo seems unaware of the fact]], but [[UnresolvedSexualTension she reciprocates these feelings.]]
* ''WesternAnimation/IronManArmoredAdventures'': Gene has a thing for Pepper, but his feelings are mostly expressed through his actions. They start off not liking each other, but they get close when Gene saves Pepper from the Maggia. He even sacrifices himself for her in the season one finale, which leads to him getting all five Makulan rings. After revealing himself to be the enemy, Gene fights and acts harshly to Tony and Rhodey, even calling them by their last names to reinforce his hatred. However, Pepper is the only one he apologizes to and is the only person he doesn't want to fight or hurt. When he shows up at Team Iron Man's base, he has a heated conversation with Tony, but when Pepper steps in, he changes to a much softer tone for her. Ultimately, when Pepper becomes Rescue, he reiterates that he doesn't want to fight her, but does so anyway.

** Emperor Awesome has a thing for Sylvia (who he insists on calling "Rebecca" or "Becks") and even suggests forcibly adding her to his entourage after capturing her in "The Party Animal." She's always quick to shoot him down.

** "The Loose Screw" implies that this kind of relationship is ongoing between aging villain Mandrake the Malfeasant and his likewise-aging superhero nemesis Stella Starbella. Though he complains that he "could never conquer [her] heart," they're definitely FriendlyEnemies at this stage if they weren't already, with Stella even bringing him back to her ship for cookies after capturing him.