History Main / DatingCatwoman

* Alex, the only real LoveInterest in the Bastard of Kosigan series is also the brains behind one of the main villain's operation. Though, due to the story's BlackAndGrayMorality, she shows up much more on the grey side of the scale than the French, the Inquisition, or the witches, so perhaps she and Mordred aren't actually villains after all.

** Elan and Therkla, though it was unrequited on Therkla's part (Elan is completely devoted to Haley).
** Elan's canon relationship with Haley has shades of this, as Haley's a rogue and only [[ChaoticGood ChaoticGood...ish]].

* The ''Disney/Hercules'' version of [[WellExcuseMePrincess Megara]] is a minion of [[EverybodyHatesHades Hades]] who [[HijackedByJesus sold her soul to him]] to save the man she loved ([[TheFirstCutIsTheDeepest who subsequently dumped her for somebody else]]).

* {{Daredevil}} has virtually made a career out of this trope. {{Elektra}}, Typhoid Mary... he never seems to learn.

* Rival Racers [[{{NASCAR}} Danica Patrick and Ricky Stenhouse Jr.]] have recently announced they are dating

* Alex, the only real {{Love Interest|s}} in the Bastard of Kosigan series is also the brains behind one of the main villain's operation. Though, due to the story's BlackAndGrayMorality, she shows up much more on the grey side of the scale than the French, the Inquisition, or the witches, so perhaps she and Mordred aren't actually villains after all.

* [[spoiler:Kohaku]] in ''VisualNovel/{{Tsukihime}}'' during her route. During the same route, there was a little with Akiha as well, but Shiki [[LikeBrotherAndSister decided that their relationship]] [[NotBloodSiblings didn't depend on blood]]. But for the main thing, it's the only way that [[spoiler:Kohaku]] actually gets to have a happy ending. In the rest, she either continues bottling up her emotions (canon personality) [[spoiler:dies or loses her memory, perhaps intentionally.]]

Compare GoKartingWithBowser, LovesMyAlterEgo, or DefectingForLove. Easily overlaps with VillainessesWantHeroes. May lead to TheMasqueradeWillKillYourDatingLife if the pairing is ultimately incompatible or too unstable. The one-sided version of this may be a VillainousCrush. See FoeYay for the less explicit version of this, and FatalAttraction when it's more dangerous. Compare FriendlyEnemies.

** Since ''Manga/KamikazeKaitouJeanne'' is heavily inspired by ''KaitouSaintTail'', Jeanne also has a romance with her main rival, [[spoiler: Chiaki aka Sinbad]].
*** Jeanne and Chiaki were justified in the manga: [[spoiler: It turns out that the two are, in fact, [[Literature/TheBible Adam and Eve]]]].

* Aimi/ShadowLady and Bright.

* Aimi/''ShadowLady'' and Bright.

* Aimi/''Shadow Lady'' and Bright in the manga ''ShadowLady''.

* ''Superior'' has this as its premise. It opens with the Demon Queen, Sheila, falling in love with the hero sent to vanquish her, Exa. She conceals her true identity - although he suspects, he cannot bring himself to confront her and doesn't want to believe it.

* ''Manga/KaitouSaintTail'' and Asuka Jr.; in this case, the ''lead'', a PhantomThief that steals back stolen items, is the Catwoman-ish one.

* ''VisualNovel/UminekoNoNakuKoroNi'' has Battler and Beatrice, whose romantic undertones are there, but not quite strong or obvious. However, in the end, it turns out that [[spoiler: not only are they romantically involved (in a way), but the romance between them is basically the cause of ''everything'' that happens in the series.]] Possibly subverted, since Beatrice is [[spoiler: not actually the real antagonist, but a faux one (although Battler believed she was the real antagonist for most of the series)]]

[[folder:Film]]
* In ''Film/{{Metropolis}}'', Freder is the son of the semi-evil Capitalist overlord, and Maria is a young Socialist reformer. It turns out okay, though.

* Sam Winchester and Ruby in ''Series/{{Supernatural}}''. The former is a hunter of supernatural monsters, the latter a demon. She eventually seduces him while mentoring him to kill other demons, and they start a physical relationship. In a later episode their foreplay jumps straight into HemoErotic territory when she lets him drink her blood, to which he is addicted. When he admits it to Dean, his brother is more than squicked out. One of the few examples in the series that isn't just one-sided FoeYay from a villain towards one of the heroes.

** One episode also has JonahHex hooking up with Lashina, depicted here as a henchwoman of Mongul and Mongal.

* In Creator/AynRand's ''TheFountainhead'' the "hatred" between critic Dominique Francon and architect Howard Roark becomes proverbial, and newspaper commentators compare it to "A Medieval vendetta." She writes articles condemning his buildings and uses all her charm to dissuade people from giving him a job. Nobody knows (though they live in New York City and are both much in the public eye) that they spend their nights together. In bed she tells him what she had done that day to destroy his career, and he laughs - knowing this is her way of showing that she really loves him. The two thoroughly enjoy acting like arch enemies in public by day and being secret lovers by night.

* ''Series/TeenWolf'': Scott and Allison. A variation in which he KNOWS she's on the opposing side, or, that her father is anyway.

* Sherlock and [[spoiler:Irene Adler, who is actually ''Moriarty'']] on ''Series/{{Elementary}}. [[spoiler:She seduced Sherlock into a relationship in order to figure him out and why he kept foiling her criminal plans, but did eventually develop real feelings for him. Once she got what she wanted, Moriarty then fakes "Irene"'s death so that she can be free to pursue her plans without Sherlock's interference.]]

* ''Anime/DragonBallZ'' does this ''twice'', though both times the aftermath is shown rather than the circumstances of their falling in love. The first to do this is Bulma, who, over the course of three years, has a relationship with former warrior prince and TheStarscream to the previous BigBad Vegeta. Interesting in that a time traveller tells the hero this will happen before it does, which [[FaceFault knocks him on his ass.]] The second instance is Krillin, who falls in love with former [[AntiVillain troubled]] enemy cyborg #18. After a time skip of seven years, it's shown that they got married and had a kid (remember, cyborg, not android...) In both cases the relationships contribute to a HeelFaceTurn (though #18 arguably had already essentially switched sides by then; it was more of a Loner Face Turn), and both formerly villainous parties act the same way: they don't show it much, but they actually care.

** To bring Blackarachnia into ''WesternAnimation/TransformersAnimated'', she became Optimus Prime's Catwoman. That is, once she gets over[[NoOneGetsLeftBehind getting left behind]].

* ''Manga/DragonBall Z'' does this ''twice'', though both times the aftermath is shown rather than the circumstances of their falling in love. The first to do this is Bulma, who, over the course of three years, has a relationship with former warrior prince and TheStarscream to the previous BigBad Vegeta. Interesting in that a time traveller tells the hero this will happen before it does, which [[FaceFault knocks him on his ass.]] The second instance is Krillin, who falls in love with former [[AntiVillain troubled]] enemy cyborg #18. After a time skip of seven years, it's shown that they got married and had a kid (remember, cyborg, not android...) In both cases the relationships contribute to a HeelFaceTurn (though #18 arguably had already essentially switched sides by then; it was more of a Loner Face Turn), and both formerly villainous parties act the same way: they don't show it much, but they actually care.

* ''Series/{{Smallville}}'', in the first of the three episodes Alicia appears in, the Clark/Alicia relationship is this trope. Afterwards, she's RefomdButRejected by all but Clark.

* Naturally, the {{Trope Namer|s}} and most famous example is the romantic tension between Comicbook/{{Catwoman}} and Franchise/{{Batman}}. The [[AlternateUniverse Earth-2]] versions of the characters actually married and had a kid, the original Huntress. [[CutLexLuthorACheck Why bother stealing when you're married to a multimillionaire?]] The main versions became a couple too, and Bruce even revealed his identity to her and she moved into the mansion with him. The relationship didn't last, but they both developed a respect for each other and Batman mostly looks the other way when Catwoman does her thing.

* Comicbook/{{Spider-Man}} and the Black Cat fit this one like a glove, though that relationship took second place to Mary Jane, who Spidey eventually married.

* CaptainAmerica dating Diamondback, a member of the Serpent Society (a group of snake-themed supervillains). This is a somewhat defanged (no pun intended) instance, as Diamondback offered to drop crime for him practically in their first meeting. (Not that she came off all that convincing, but...)

** Also, he eventually got into a relationship with Comicbook/BlackWidow, a former enemy.

* Comicbook/CaptainAtom wound up ''marrying'' Plastique, a former Quebecois terrorist with explosive powers. Appropriately, in ''[[WesternAnimation/JusticeLeague Justice League Unlimited]]'' she [[spoiler: [[DiedInYourArmsTonight died in his arms]]]].

* TheMightyThor and The Enchantress (Amora), a goddess of Asgard, who spent years hatching plans to harass and seduce the god of thunder. He eventually relented and had a brief romantic relationship with her.

* Statonian Envoy Rhodney Antilles and [[TheEmpire RMM Agent]] Melanie Horquetza in ''StationeryVoyagers''. It helps that Lord Abberwadd [[AntiVillain treats the Voyagers]] more as rebellious children than as actual enemies.