History Main / UnholyMatrimony

* The ''Series/{{Arrowverse}}'' crossover ''Series/CrisisOnEarthX'' has Dark Arrow and Overgirl, the Earth-X {{Evil Doppelganger}}s of Oliver and Kara, respectively, who are married. Supergirl is vocally grossed out by this.

* [[Series/BuffyTheVampireSlayer The Buffy]][[Series/{{Angel}} verse]]:

** Vampire Willow and Vampire Xander, much to Cordelia's exasperation. Besides killing people, their relationship involves Xander watching Willow brutally torture people.
%% ** Lindsey and Eve; she even gave up her immortality and role as liaison to the Senior Partners for him.

* In the ''Series/{{Charmed|1998}}'' episode "[[Recap/CharmedS4E15MarryGoRound Marry-Go-Round]]", if someone wants to remain aligned with Evil in marriage, it must be performed with a Dark Priest, at night, in a cemetery.

* ''Series/{{Daredevil|2015}}'': Wilson Fisk (a.k.a. ComicBook/TheKingpin) meets art museum curator Vanessa and falls in love with her. After going on a date and learning just who he really is, she falls in love with him. She supports him unquestionably as our hero Matt Murdock tries to tear down Fisk's empire. At the end of the first season, he proposes to her [[spoiler:''as he's being dragged away by the FBI'']].

* ''Series/LoisAndClark'': Had a rich SickeninglySweethearts couple who kept their marriage alive by brewing evil plans together.
* ''Series/TheMentalist'': In episode "Red Hair and Silver Tape", a couple who owns and runs a luxurious restaurant kidnap girls with the intention to murder them. Jane first suspected only the husband. Agent van Pelt especially is horrified to learn that they were in it together.

* ''WebVideo/NightmareTime'': "Forever and Always" has [[spoiler:Not-Emma and Paul 23, an android and clone, respectively, who independently pulled a KillAndReplace on the real Emma Perkins and Paul Matthews, then met each other and fell in love. The episode starts with Not-Emma [[ConfessToALesserCrime admitting she took over the real Emma's life (leaving out the fact that she orchestrated her death)]] and Paul saying he still loves her and wants to be with her regardless. Things escalate from there, and the episode ''ends'' with the two dumping a dead body, planning to murder a homeless man because HeKnowsTooMuch, and fondly reaffirming their love for each other. If anything, their relationship gets ''stronger'' once all the murderous cards are on the table, because there are no more secrets between them.]]

** [[AntiVillain Zuko]] and [[AloofDarkHairedGirl Mai]], for the brief time in the third season while they're in a steady relationship and both are sided with the Fire Nation. It falls apart after Zuko undergoes his HeelFaceTurn and leaves Mai behind, but there's clearly lingering feelings on both ends by their next meeting, [[spoiler: and [[LoveRedeems her love for Zuko]] ultimately drives Mai to backstab Azula and make a HeelFaceTurn of her own]]. Whether or not they actually ended up together remains to be seen as they've broken up in the comics and the creators have outright ignored questions about who the mother of his daughter, Izumi, is (though she and Mai have the same distinctive face shape).

* One episode of ''WesternAnimation/CareBears1980s'' has Professor Coldheart convince villainess Auntie Freeze that he wants to marry her and asking the Care Bears for help throwing the wedding. The gullible Care Bears agree, reasoning that anyone capable of love can't be bad. The reason is to sneak in an organ loud enough to destroy the cloud kingdom and crash the bears down to Earth, but when Auntie figures out that it's a sham, she just twists his ear and leasd him off to receive punishment...

* ''WesternAnimation/MoralOrel'': [[spoiler:Clay and Ms. Censordoll]], at first competing in office, end up making out with each other at the end of "Nesting." They share a mutual infatuation with eggs, the former due to his [[spoiler:[[ChildSupplantsParent Oedipus Complex]]]] and the latter due to [[spoiler:having been "castrated" as a child]].
* ''WesternAnimation/TheMummyTheAnimatedSeries'': Anck-Su-Namun is even ''worse'' in the AnimatedAdaptation. Which is saying something, considering the movie version ''threw venomous snakes at people''. It's implied in the cartoon that Anck-Su-Namun was just in a relationship with Imhotep for chance at achieving power; after he goes through the trouble of resurrecting her, she abandons him the moment she gets her hands on the ArtifactOfDoom [[MacGuffin of the week]]. When they encounter each other again in the series finale, Imhotep is apparently over her, as he leaves her to rot in the Underworld in an AndIMustScream state.
* ''WesternAnimation/OKKOLetsBeHeroes'': Starting in the episode "[[Recap/OKKOLetsBeHeroesS1E18WereCaptured We're Captured]]", Lord Boxman begins courting Professor Venomous. [[spoiler:They later move in together, forming a [[BlendedFamilyDrama blended family]], and are seen wearing wedding rings in the finale, hinting that they got married.]]
* ''WesternAnimation/TheOwlHouse'': While it's clear that Odalia [[HenpeckedHusband wears the pants in their relationship]], Alador and Odalia have a surprisingly functional marriage (it's even implied during a flashback that [[HighSchoolSweethearts they've been together since their school years]]). He makes the weapons she sells, her social graces make up for his lack of tact, and she genuinely praises his abomination-making skills a few times. Too bad they're both AbusiveParents and ruthless, money-driven, image-obsessed, and [[BlueBlood blue-blooded]] arms dealers. Ultimately subverted in "[[Recap/TheOwlHouseS2E20CloudsOnTheHorizon Clouds on the Horizon]]"; [[spoiler:it's made clear their relationship is strained as Odalia only seems to view Alador as a business partner instead of a romantic one, and when her lack of ethics go too far, Alador quits and sides with their children over her]].

%%* [[BigBad Dio Brando]], a century-old vampire and [[WellIntentionedExtremist Enrico Pucci]], a morally ambiguous catholic priest make up for a very interesting case in ''Manga/JoJosBizarreAdventure''. Although it's still controversial if they are this or [[VillainousFriendship villainous friends]], the author himself has lately confirmed Dio to be into both men and women. Or at least, willing to use sex to manipulate either.

%%* Hunt and Sarah from ''Manga/TegamiBachiLetterBee''.
%%* Kriem and Jake Martinez in ''Anime/TigerAndBunny''.

%%** Sensui and Itsuki are a rare [[HoYay homosexual]] example. Well, [[SplitPersonality sometimes]]...

%%* [[MonsterClown Li'l Ronnie/Ran-Ru]] and her Servant [[ActuallyNotAVampire Lancer]] in ''VideoGame/FateExtra''.
%%* [[LadyOfBlackMagic Caster]] and [[spoiler:Kuzuki Souchirou]] in ''VisualNovel/FateStayNight''.
%%* In ''VisualNovel/HatePlus'', [[spoiler:Ryu and Oh Eun-a]].

** There was also the rather...twisted relationship between the EvilSorceress Iggwilv and the demon lord Graz'zt; they were lovers for a time, he helped her forge an empire, and she bore his son, who would grow up to be the cruel tyrant Iuz...all despite the fact that [[StockholmSyndrome she had technically kidnapped him and was holding him prisoner]]. It ended ''very'' badly. (Oddly enough, while some sources have claimed that Graz'zt has killed minions for simply bringing it up, a Fourth Edition write-up on Graz'zt claims that Iggwilv is his "ally and occasional lover". Given how chaotic demons are, ''anything'' is possible, though 4th Edition was known for at best only having BroadStrokes canon from previous editions.)

*** In ''ComicBook/WonderWoman1987'' Circe plays a MemoryGambit in order to get close to ComicBook/{{Ares|DC}} without him realizing it's her, since even she thinks she's the AmoralAttorney Donna Milton. As Donna she grows to honestly trust and love Ares and they have a child together before the relationship goes south.

* Subverted in Episode Five of ''Webcomic/{{Demonology 101}}'', when [[spoiler:Isaac, the main villain, and Madeline, his demon 'handler,' genuinely falls in love halfway through the episode. She was supposed to keep him out of trouble, but once she starts sympathizing with him, winds up encouraging him to kill his brother Gabe. (As if he needed more encouragement.) However, when she herself is fatally injured, Isaac willingly barters her cure for a final truce with Gabe and the other protagonists]].

* Didi and Gogo in ''[[http://vanheist.deviantart.com/art/fine-young-cannibals-87201971 Fine young cannibals]]'' by [=VanHeist=], inspired by ''[[Theatre/SweeneyToddTheDemonBarberOfFleetStreet Sweeney Todd]]''. Aren't they a cute pair?
* Occurs between [[MadScientist Mad Scientists]] Spencer Ecchs and Ada Byon in ''Webcomic/PatchworkChampions''. [[spoiler: She seduces him on the orders of another supervillain to steal his secrets, but when she carries out her mission successfully, the two continue to date, ending with her joining Ecchs's group and marrying him.]]

** ''ComicBook/ThePunisher'': During [[Characters/{{Daredevil}} Stilt-Man]]'s funeral, it's revealed that he and Princess Python from the Circus of Crime had been married. Later ''Punisher'' arcs showed that Princess Python tends to do this... she's been married many times, ALWAYS to another supervillain, most recently the Gibbon.