[[quoteright:224:[[VideoGame/BatmanArkhamCity http://static.tvtropes.org/pmwiki/pub/images/bat_and_cat_01_7179.jpg]]]]
[[caption-width-right:224: One man's fight is another man's date.]]
->''"We conducted our courtship on rooftops and fire escapes. A strange flirtation, a hide and seek, a game of cat and mouse..."''
-->-- '''Catwoman''', ''ComicBook/WhateverHappenedToTheCapedCrusader''

When the hero of the show and one of the antagonists have a romantic tone right out in the open, as opposed to FoeRomanceSubtext. This adds a degree of tension to the relationship, and as long as you make sure the antagonist is [[AntiVillain less of a "villain"]], we're allowed to root for them.

Their different senses of morality will conveniently keep things from progressing too quickly and sometimes they won't move at all, since the character [[TheVillainMakesThePlot won't be as fun]] if [[HeelFaceTurn they go straight]]. The same concerns about getting rid of the dramatic tension that fuel WillTheyOrWontThey apply here.

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 FoeRomanceSubtext for the less explicit version of this, and FatalAttraction when it's more dangerous. Compare FriendlyEnemies.

[[IThoughtItMeant Has nothing to do with]] dating a CatGirl. Usually.
----
!!Examples

[[foldercontrol]]

[[folder: Anime and Manga]]
* Manga/KaitouSaintTail and Asuka Jr.; in this case, the ''lead'', a PhantomThief that steals back stolen items, is the Catwoman-ish one.
* 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]]]].
*** And both them hearken back to the original Japanese heroic thief-girl and her policeman pursuer in ''Cat's Eye''.
* The usual tone is subverted in ''Manga/TokyoMewMew'', where the romantic hero and villain are... a GenkiGirl and a BrattyHalfPint, each the "annoying kid" of their team.
** There also is a one-sided romance between Quiche and Ichigo, with the former being madly in love with the latter. His love gets [[{{Yandere}} creepier]] as the show goes on... [[spoiler: until the end when Quiche refuses to kill Ichigo and gets killed himself. Ichigo is genuinely upset by his death. He gets better, though.]]
* ''LightNovel/{{Dokkoida}}'' combines this with the UnwantedHarem; the male superhero, his (female) [[TheRival Rival]], and all the supervillains (who are almost all female) [[LivingWithTheVillain all live in the same apartment building and hang out together]] when disguised as {{Muggles}}.
* In ''Anime/UFORoboGrendizer'' -one of the ''Anime/MazingerZ'' sequels-, Duke [[spoiler:was engaged to Rubina, daughter of BigBad.]] They loved each other. However he did not think they could be together again after what the Vegans had done to his homeworld.
* Aimi[=/=]ShadowLady and Bright.
* ''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.
* In ''Manga/SpecialDutyCombatUnitShinesman'', Matsumoto, a young businessman who is [[SecretIdentity secretly a superhero]] protecting the Earth, accidentally sees a bare skin of Princess Sheena, one of the villains from the Planet Voice who are trying to conquer the Earth. Due to the rule of Planet Voice that whoever sees bareskin of the royalty must either die or marry the royalty, Matsumoto and Sheena start dating, unaware of each other's secret identity.
** In the manga, Sheena didn't exist, so this incident happened between Matsumoto and Sasaki/Prince Hope instead. Sasaki [[spoiler:definitely embraces the 'kill him' option until the very end of the manga, when he tells Matsumoto he's changed his mind.]]
* This is largely the point of the romance between the primary OfficialCouple in ''Manga/WeddingPeach'', who are directly inspired by ''Theatre/RomeoAndJuliet'' which would make them fit the StarCrossedLovers trope but luckily [[spoiler:everything ends up ending well for them]].
* TeamChef Sai Saici and PluckyGirl Cécile (the sister of Gundam Fighter Hans Holgar) in ''[[Anime/MobileFighterGGundam G Gundam]]''. Causes less problems than most examples, since Hans is no mortal enemy, but a decent, friendly WorthyOpponent in a sports tournament.
* Happens in ''Anime/RedGarden'' when Kate ends up dating [[spoiler:Hervé, a member of the family responsible for the wild men she and the other girls fight]]. She's oblivious about his real role in things, but he knows hers from the very start.
* ''[[Anime/MobileSuitGundamZZ Gundam ZZ]]'' has an unusual situation wherein the LadyOfWar ''BigBad'', Haman Karn, grows attracted the [[{{Shotacon}} much younger hero]] Judau Ashta. Judau displays some degree of concern for Haman, although how much of it was a romantic interest is open to debate. [[UnwantedHarem Judging by how the ladies get interested in him...]]
* ''Manga/{{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.
* There are hints that Hayato has some form of romantic attraction (or at least deep respect for) Keith Violet in ''Manga/ProjectARMS'', although it seems to be mostly one-sided. [[spoiler:Keith Green also falls for Katsumi, although again it's one-sided (she has no idea]].
* Ruby and Courtney from ''Manga/PokemonSpecial'' form a strange relationship as time goes on, eventually leading them to team up against Kyogre and Groudon. Ruby does eventually care for her in a platonic manner, but Courtney ''definitely'' feels something stronger for him. Kinda creepy considering he's 11 and she's assumedly in her late-teens/early twenties. Heck, she even went so far as researching his background! (Though that did lead to her discovering information that made realize all that his father sacrificed for his sake).
* Sankt Kaiser Olivie Segbrecht and Hegemon Klaus Ingvalt of ''MagicalGirlLyricalNanoha''. Despite being [[WarriorPrince rulers]] of opposing sides in the Ancient Belkan War, Klaus was enamoured with Olivie, and his regret of failing protect to her in the end was so strong [[GeneticMemory that the rare descendant who would inherit his traits]] could feel it over the centuries.
* Bizarre example in ''Manga/TheLuciferAndBiscuitHammer'', where the two people are technically on the same side ''at the present'' due to an EnemyMine, but nevertheless one wants to destroy the world and the other wants to save it.
-->'''Snake Knight:''' If, at the very end, I win and stop the two of you [from destroying the world], would you go out with me?
-->'''Lizard Knight:''' I... I'll think about it.
** By the end of the series, [[spoiler:the relationship between the Lizard Knight and the Princess becomes something akin to this when he decides that he won't let her destroy the world because he loves her. She's actually happy that he's trying to stop her.]]
* In ''{{Robotech}}'', the Zentraudi ace pilot Miriya Parino falls in love with Terran ace pilot Max Sterling, after literally engaging in several duels and stalking him with intent to murder. They marry and have a child, Dana, who goes on to pull something of the same thing with the Robotech Master ace pilot Zor Prime (a clone of the original superintellect Zor).
* The central romance in ''Manga/CatsEye'' is between ClassyCatBurglar / MasterOfDisguise Hitomi and [[PoliceAreUseless Bumbling Cop]] Toshio.
* ''AkameGaKiru'': Esdese is truly and completely in love with Tatsumi. Esdese just happens to be an insane sadist working for an extremely corrupt government and Tatsumi is a member of a rebel group trying to topple said government. Well Esdese is unaware of this fact, Tatsumi tried a LoveRedeems on Esdese more than once, trying to use her love for him to make her become good, but gave up quickly when he realized Esdese is completely insane and can't change.
* ''The whole premise'' of LightNovel/MaoyuuMaouYuusha. The Hero and the Demon Overlord both say "ScrewDestiny" to their respective roles, hook up and try to find a way to end the war without gutting their respective war economies.
[[/folder]]

[[folder: Comic Books]]
* 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.
** However, things got a bit more interesting with the two. Continuing to dance around one another constantly to the point of a nearly functional relationship, then to a distant one due to fear of repercussions from their knowledge of one another's identity, the couple have certainly reheated things a bit since Bruce's return to the present... long story. Regardless, she has even accompanied him on his international travels to establish Batman Inc. Maybe not a perfect relationship, but hey.
*** Unfortunately for those who may have enjoyed it, all that CharacterDevelopment in their relationship has been set back to square one with the [[{{New 52}} 2011 DC Universe reboot]], in which Catwoman has no idea who Batman is behind the mask (although she suspects he knows who she is). Doesn't [[spoiler: stop her from having costumed sex with him though]].
** Funnily enough, the whole 'dating Catwoman' trait stems from the fact that Batman himself has [[AllGirlsWantBadBoys a weakness for villainesses]], which he acknowledged in ''Batman R.I.P''. His relationship with [[MadScientistsBeautifulDaughter Talia al Ghul]] in the main continuity (where they have a son together) is similar with his relationship with Catwoman.
*** In ''Comicbook/GothamCitySirens'', it was mentioned that Catwoman and Talia are probably the only two women Batman has truly loved. It's not surprising that both of them are villainesses.
** Very explicit in one standalone strip called "Date Night"; Batman catches Catwoman in the middle of a robbery and chases her through various romantic locations including a flower stall and a fancy restaurant, all the while Catwoman is talking and flirting with him as if they were actually on a date. When he finally catches her, they briefly fight and she leaves him tied up and dangling upside down from a fire escape, kisses him goodnight and runs away.
** In ''Batman the Dark Knight'' after the 2011 reboot, Bruce is attracted to Jaina Hudson, but becomes suspicious of her after new villainess White Rabbit issues the same "Catch me if you can" flirtatious challenge Jaina made in their first meeting. His suspicions are debunked when the White Rabbit shows up on the radar while he is on a date with Jaina. [[spoiler:It turns out he was right after all, since Jaina has the power to split herself into two people -- her normal self and the White Rabbit.]]
** In an issue of ''Comicbook/TheBraveAndTheBold'' in which Superman patrolled Gotham in Bruce's stead, Catwoman quickly developed a crush on the Man of Steel on first sight. The two work together to take down a shady auction, with Selina treating it as a date.
* ComicBook/SpiderMan and the Black Cat fit this one like a glove, though that relationship took second place to Mary Jane, who Spidey eventually married.
** Though that particular possibility has now been reopened, due to a CosmicRetcon. Furthermore, Felicia actually stated on more the one occasion that Peter's marriage vows meant absolutely nothing to her. The second she sees an opportunity to talk him out of his tights, she's taking it.
* ComicBook/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...)
* Comicbook/IronMan and Madame Masque/Whitney Frost. Then again, it's not surprising considering [[ReallyGetsAround the number of paramours]] Tony's had over the years. It came to the point where Frost [[StalkingIsLove masqueraded as Tony's personal secretary]] after they first broke up and resumed their relationship once her cover was blown.
** Also, he eventually got into a relationship with ComicBook/BlackWidow, a former enemy.
*** And Masque hooked up with TheHood.
* 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]]]].
* [[TheSilverAgeOfComicBooks Silver Age]] Creator/MarvelComics tended to see this pop up a great deal with heroines and manly-man opponents -- e.g. the [[Comicbook/FantasticFour Fantastic 4's]] Sue Storm to the {{Sub-Mariner}} (while he was a functional villain), or the ScarletWitch towards Arkon (who later dated {{Storm}}, but his relationship with the Comicbook/{{X-Men}} was on friendlier terms). Arguably, this resulted less in creating interesting tension than just creating [[FauxActionGirl a less effective heroine]].
* ComicBook/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.
* {{The Golden Age|OfComicBooks}} Franchise/GreenLantern, Alan Scott, not only fell in love with the villainess Thorn, he had ''children'' with her. Then again, he ''did'' fall in love with her [[SplitPersonality good personality, Rose]]. His second wife, the Harlequin, also started out as one of his adversaries, although she was long reformed and retired by the time they married.
** Making this trope happen is actually the entire reason Harlequin turned to crime. She wanted to catch Lantern's eye, and decided that donning a sexy costume and alternately stealing things and teaming up with him would be the best way to attract his attention.
** Likewise, the Silver Age Green Lantern, Hal Jordan, had Carol Ferris (whose [[SuperpoweredEvilSide Star Sapphire personality]] made frequent appearances) as a long-time love interest.
* Reversed in the case of Ray Palmer, the Silver Age [[TheAtom Atom]]. His wife Jean Loring became the villain Eclipso after their marriage and divorce... and [[spoiler:[[ComicBook/IdentityCrisis after she went nuts and killed Sue Dibny and Jack Drake]]]].
** His successor as Atom, Ryan Choi was dating Giganta. It was apparently a serious enough relationship that [[spoiler: she took vengeance on his murderer]].
* {{Creator/DC|Comics}}'s Roy Harper (a.k.a. Speedy/Arsenal/Red Arrow/whatever they're calling him this week) was sent in to seduce batshit insane assassin Cheshire to get enough evidence to take her in. However, they fell in love with each other and Roy realized he wouldn't be able to do it and walked out... not knowing Cheshire was pregnant. Cheshire herself didn't find out who Roy was until it was all said and done, and then arranged for Roy to get permanent custody of Lian. Cheshire is also the victim of emotional blackmail because Mockingbird put her on the Secret Six by threatening Lian with an explosive device he supposedly implanted.
* Captain Dynamo and Chrysalis from ''{{Dynamo 5}}''.
* Comicbook/{{Daredevil}} has many. ComicBook/{{Elektra}}, Typhoid Mary, etc. While the Comicbook/BlackWidow had long reformed when she got involved with ComicBook/{{Daredevil}}, her previous relationship with {{Hawkeye}} had an element of this for a time, between his HeelFaceTurn and hers.
* ComicBook/{{Superboy}} (1990s clone version) dated ComicBook/{{New God|s}}dess Knockout, under the impression she was a well-meaning thrillseeker, rather than a murderous sociopath.
* Franchise/{{Superman}} had a sexual relationship with New Goddess Amazing Grace. And Maxima. Oh, and he ''married'' the Kandorian Lyla (he had amnesia).
* Comicbook/{{Witchblade}} bearer and cop Sara Pezzini and Darkness bearer and Mafioso Jackie Estacado are rivals in their professional and supernatural lives, but as of ''First Born'' they [[spoiler:have a daughter, Hope, together.]]
* When inept superheroine Comicbook/{{Empowered}} met Thugboy, the love of her life, she was tied to a chair and he was part of the gang holding the hostage she was attempting to rescue for ransom. He whispered a few words of encouragement into her ear... and pulled her out of the way when one of her idiot teammates brought the building down. Empowered then lets herself get captured by his gang several more times just to have an excuse to keep seeing him. He does a HeelFaceTurn a few chapters later.
* In ''[[http://johnnysaturn.com/2006/01/18/book-one-page-01/ Johnny Saturn]]'', Johnny Saturn I is married to Persephone, the daughter of Saturn's arch-enemy, Dr. Synn. Persephone is morally ambiguous, and as likely to use her powers to aid her father as her husband.
* Subverted with the [[ClassyCatBurglar Ireyon]] in ''{{Paperinik|NewAdventures}}'' - she comes onto [[WesternAnimation/DonaldDuck our masked hero]] because she thinks he is [[GentlemanThief Fantomius]], her old flame, whose style and equipment Donald uses for regular superheroing. Donald isn't that interested, and vaguely annoyed she thinks he is as old as his grandpa. (She, on the other hand, is ReallySevenHundredYearsOld.)
* Greyshirt of ''ComicBook/TomorrowStories'' has Lapis Lazuli. He really does love her, but, well... if they ever got together in any meaningful way, she'd probably kill him the second it went sour. Even she thinks so.
* ComicBook/{{Huntress}} and [[ComicBook/SecretSix Catman]] had an on and off relationship ever since they fought for the first time. While it never got further than intense FoeYay, they still cared deeply for one another. Huntress never stopped hoping Catman would be redeemed, and Catman for his part appreciated it even though he believed he was beyond redemption. Catman enacted a ridiculously complicated scheme to make Huntress give up on him because [[IWantMyBelovedToBeHappy he wanted her to be happy with someone else.]] Catman had just been through a TraumaCongaLine that convinced him that he didn't deserve ''anyone's'' love, least of all Huntress'.
* Zorro and LadyRawhide in Topps ''Franchise/{{Zorro}}'' series.
* Comicbook/TheSpirit has at least ''three'' - Silk Satin, Sand Saref, and P'Gell.
* In ''ComicBook/FinalCrisis'', [[JusticeLeagueOfAmerica Snapper Carr]] hooks up with the Cheetah.
* In ''{{ComicBook/WITCH}}'', Orube fell in love with [[ManipulativeBastard Cedric]], and they dated until his [[spoiler: RedemptionEqualsDeath]].
* Karolina Dean of the ''ComicBook/{{Runaways}}'' first encountered her current girlfriend Julie Power back when the latter was part of a group that had been organized specifically to shut down the Runaways. They later hooked up after Julie's then-employer Hank Pym tried to kidnap Molly Hayes and Klara Prast.
* It is revealed in ''Comicbook/{{Watchmen}}'' that Night Owl II had a fling with Twilight Lady.
* ComicBook/{{Supergirl}} (not the original, a shape-changing alien called Matrix posing as her) had a sexual relationship with LexLuthor (who had put his mind into a cloned body of his younger self).
* Prior to the ''Comicbook/{{Flashpoint}}'' reboot, Red Robin was sort of dating the second Lynx, who was either a gang-leader or a Hong Kong cop undercover as a gang-leader. The irony that he was in a relationship with a possible-villain in a cat mask was not lost on him.
[[/folder]]

[[folder:Fan Works]]
* Manga/DetectiveConan BoysLove Fanworks are full of this, since the most popular pairing is between the title character Conan Edogawa/Shinichi Kudo and his PhantomThief rival [[WorthyOpponent Kaitou Kid]]. Alternately Kid can also be paired with his other biggest rival [[ButNotTooForeign Saguru Hakuba]] or even Conan's best friend and fellow detective [[TheIdiotFromOsaka Heiji Hattori]], [[ShipsThatPassInTheNight though they've never met.]] This also applies to the rare times when Kid and Shinichi's fathers get paired up.
** Not just the yaoi. Even if a character in Detective Conan isn't a detective or affiliated with the police, they still usually have a thing for following the law, which means that pretty much any pairing involving Kaito is this, including his canon pairing.
* Happens a lot in ''Pokémon'' fanfiction, where it seems like every generation has had at least one popular ship pairing a rival (or even villain) up with a hero. The ready supply of attractive villains probably has something to do with this.
* This is very common in ''Manga/DeathNote'' fanworks which has pairings such as Light (Kira, a KnightTemplar SerialKillerKiller) and L (the detective trying to catch him), Mello and Near (a mafia lord and a detective who are rivals), L and B (a detective and a SerialKiller), Naomi and B (again, a detective and a SerialKiller), even Light and Misa (which has the dynamic [[YouHaveOutlivedYourUsefulness I'll kill you if you are no longer useful]] [=/=] [[{{Yandere}} I'll kill you if you cheat on me]]) In fact Mello x Matt is the only popular ship in the ''Manga/DeathNote'' fandom where both parties are completely on the same side and aren't trying to kill each other.
** Light/Kira and L is the most popular ship. Here's a few examples of DatingCatwoman in fanworks with Kira and L: ''FanFic/ACureForLove'', ''FanFic/ConstantTemptation'', ''FanFic/IWontSay'', ''FanFic/OfficePolitics'', ''FanFic/ThePrinceOfDeath''
** ''FanFic/AllYouNeedIsLove'' [[CrackPairing ships Light and Naomi]]. [[spoiler: They have "Victory Sex" once and Naomi ends up having Light's child, which she conceals from everyone.]] And that's the most normal thing that happens in that wonderfully bizarre and light fic.
** {{Lampshaded}} in ''FanFic/FeverDreams'' when L gets him and Light some matching tracking devices which he uses when he keeps Light under house arrest and nicknames them "the wedding bands."
* In Shadow Snark Twilight Sparkle and Uma o Henko Suru a changeling
* Frequently crops up in ''{{Glee}}'' fics. Usually a member of New Directions starts dating one of their bullies or someone from a rival glee club.
* A good fifty percent of all KimPossible fics seem to be focused on [=KiGo=]... that is Kimmie and Shego becoming an item... and like as not having kids and getting married... sometimes in that order.
* In ''FanFic/VoldemortGoesBackToSchool'', when Voldemort (in the body of a teenager) infiltrates Hogwarts as a new student in the hopes of killing Harry, Hermione notices that the new Slytherin kid keeps sending Harry [[DeathGlare "heated stares"]] and comes to the conclusion that he has a crush on him. HilarityEnsues.
-->'''Voldemort:''' [[ForcefulKiss This]] was ''not'' how ''wizards'' dueled!
* There is plenty of fanfiction that tends to pair [[WesternAnimation/DannyPhantom Danny]] with Ember Mc Lain.
* There's even a good amount of ''Franchise/CrashBandicoot'' fanfiction where the titular hero gets paired with Nina Cortex, [[DarkActionGirl of all girls]].
* In ''FanFic/MegaManRecut'', Future!Roll dated Crash Man, though she claims it wasn't serious. She also dated Enker.
** Present!Roll has a crush on Enker as well.
[[/folder]]

[[folder:Films -- Animated]]
* ''WesternAnimation/TheIncredibles'': Mirage and Mr. Incredible (though the extent of their relationship is very unclear). Of course, the fact that Mirage [[spoiler: ends up apparently turning good anyway and helping the protagonists]] makes it more questionable. Really only a partial example as they were never really in a relationship (Mr. Incredible already being married and Mirage respecting that.), but their flirtatious banter, while standard for superheroes, ''did'' have strong subtext of being an emotional affair on his part.
** One of the DVD extras is an explicit reference to this trope: In the background info on the Supers, there's an audio clip where TheCasanova Gamma Jack describes how difficult it is to fight attractive female supervillains.
*** Subverted a bit in that Gamma Jack is also implied to be a [[FantasticRacism superhuman supremacist]] and thus [[SociopathicHero not a nice person]] at all.
* 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]]). She reluctantly helps him try to kill [[TheHero Hercules]], but [[http://www.youtube.com/watch?v=I_bEWXs_FX4 begrudgingly]] finds herself falling for his [[DumbIsGood simple goodness]].
[[/folder]]

[[folder:Films -- Live-Action]]
* 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.
** In another Creator/FritzLang film, ''Film/{{Spies}}'', the good guy spy falls in love with the beautiful agent of the NebulousEvilOrganization. They also turn out OK.
* ''Film/OutOfSight'' involved a romance between George Clooney's gentleman bank-robber character Jack Foley, and Jennifer Lopez's US Marshal character Karen Sisco. Notably, in a change from the novel, Karen appears to deliberately plant an escape artist in Jack's prison transport so she can keep chasing him.
* ''Film/{{DEBS}}'': both the short and full-length versions of this film center around a secret agent's forbidden [[HoYay Les Yay]] romance with a {{supervillain}}ess.
-->'''Amy:''' If you'll excuse me, I have a date with the devil.
* ''TheThomasCrownAffair''.
* Most ''Film/JamesBond'' movies include some sexual tension with any female antagonists present (or at least the attractive ones), but in most cases, it's either part of the villains' [[HoneyTrap plan]] to kill Bond, or the ladies [[HighHeelFaceTurn became good]] when the BigBad mistreated or betrayed them. ''Film/FromRussiaWithLove'', ''Film/{{Goldfinger}}'', and ''Film/LiveAndLetDie'' are the only ones where the henchwoman genuinely becomes a love interest.
* ''Film/TheDarkKnightRises'' has this dynamic from early in the movie as Bruce shows a far more playful tone with Selina than his other enemies. Over the course of the movie their mutual attraction slowly develops [[spoiler:and they ultimately end up creating new identities and leaving Gotham together]].
* ''Film/BatmanReturns'', which makes Catwoman a good bit more sympathetic, if somewhat more insane (she's [[spoiler:more in the crime business to get revenge on her murdering boss and knows she can't live with herself when it's over]]).
* ''Film/{{Catwoman}}'' has Catwoman and Tom Lone, though it's more between her "good" civilian side (when she tries to make moves on him as Catwoman, she is rejected to "[[LovesMyAlterEgo I'm already seeing someone]]").
* ''Batman XXX'' has Batman ''and'' Robin "dating" Catwoman.
* Film/SherlockHolmes and Irene Adler definitely have an air of [[UnresolvedSexualTension UST]] and Irene kissed him at one point (though he was drugged). Most Holmes adaptations follow this portrayal, although the original Irene Adler of "A Scandal In Bohemia" was technically not a criminal.
** In the second film, they kiss again and arrange a dinner date. Holmes is later shown to be [[spoiler:quite despondent over her death at the hands of Moriarty, and adds revenge to his motives for going after him.]]
* This would have been the premise of the unmade ''Romance of Franchise/ThePinkPanther'', which was ultimately scuppered after lead actor/co-writer Creator/PeterSellers died: Inspector Clouseau falls in love with a woman who's actually the ClassyCatBurglar he's trying to capture.
* The plot of ''Film/{{Entrapment}}'' is based almost completely on this trope.
* Warren Peace, an AntiHero type character in ''Film/SkyHigh'' is a product of such a pairing.
* ''Film/{{Lifeforce}}''. The astronaut protagonist is obsessed with the beautiful space vampire he is hunting, even though to [[KissOfDeath touch her means death]]. They nevertheless make out several times. There's even a HoYay moment when he's driven to kiss her while she's [[BodySurf occupying the body]] of a man. He later discovers the reason for his obsession is that she took the image of the perfect woman from his subconscious.
* Duke and the Baroness from ''Film/GIJoeTheRiseOfCobra''.
* Played straight in IndianaJonesAndTheLastCrusade. Indiana and Elsa Schneider first meet in Venice and begin a sexual relationship as they look for clues to the HolyGrail’s location. However, Elsa turns out to be a Nazi supporter and this sets up a tense back-and-forth relationship for the rest of the film. With the grail finally in her hands, Elsa activates an earthquake trap that causes the temple to collapse. In the end, Indy is willing to forget her past deeds and tries saving her from falling in a chasm. Elsa, unfortunately, is too obsessed with getting the grail at any cost, and she tries reaching for it with her free hand. She refuses to give up, even though she's slipping from Indy's grip. She can’t reach it in time and falls to her death.
[[/folder]]

[[folder:Literature]]
* In ''Literature/{{Everlost}}'' [[Literature/TheSkinjackerTrilogy and its sequels]], Nick and Miss Mary Hightower.
* Corran Horn and Mirax Terrik of ''Comicbook/XWingSeries''. He's a former space cop turned pilot. She's a smuggler. His father was the one who finally landed her father in jail. Still, she's a smuggler on the Rebellion's side, is like a sister to his commanding officer, and doesn't smuggle anything too nasty. They make it work. Even if her father objects strongly.
** The later Wraith Squadron books have another one between Myn Donos, the Wraiths' sniper who lost his whole squadron in an Imperial ambush, and Lara Notsil, [[spoiler:really Gara Petothel, an Imperial spy who planted the information attracting them to the ambush. After flying with the Wraiths in disguise for a while she ends up BecomingTheMask and falling in love with him. She's forced to fake her death, but ''Mercy Kill'' reveals they eventually found each other and are HappilyMarried with children.]]
* Luke and Mara in Literature/TheThrawnTrilogy and, of course, Literature/HandOfThrawn. He's the last of the Jedi, she's the former personal assassin of the Emperor who wiped out the Jedi. Then he rebuilds the Jedi and she becomes second in command of one of the largest criminal organizations in the galaxy. Of course, despite the Jedi theoretically being keepers of law and order, said criminal organization ends up being one of their most reliable allies and gets less and less criminal as time goes on.
** And of course, their son Ben [[WillTheyOrWontThey may perhaps become]] involved with a Sith girl, Vestara Khai. There's certainly high amounts of UST. Bear in mind that the Jedi and Sith have existed largely for the specific purpose of opposing each other for thousands of years, and ultimately the conflict dates to before either order actually existed.
* There's the fan-favorite of the demon Crowley and the angel Aziraphale in Creator/TerryPratchett and Creator/NeilGaiman's ''Literature/GoodOmens''. They're MistakenForGay in the book, and WordOfGod is that they end up sharing a cottage in South Downs. Not quite a textbook example, as by the time of the book they've decided they have more in common with one another than either of them has with his respective boss, and have an Arrangement. In addition, this is more like [[HeterosexualLifePartners Asexual Life Partners]], due to the very nature of angels and demons.
** Played straight with Anathema, who's a witch, and Newt, who's a witch-hunter, albeit a not-very-enthusiastic one.
*** Technically, Newt is a Witch-''Finder''. And... well, [[ExactWords he found himself a witch]].
* John Taylor, from the ''Literature/{{Nightside}}'' novels, had a brief affair with Bad Penny, an assassin-for-hire. Upon his return from London, they wind up trying to kill each other.
* ''Literature/TheScarletPimpernel'': Sir Percy and Marguerite Blakeney lived estranged for a year (during which the latter [[LovesMyAlterEgo fell in love with his alter ego]]) before Marguerite's HeelRealization and [[TheAtoner redemption]].
* In Creator/HarryHarrison's ''[[Literature/TheStainlessSteelRat Stainless Steel Rat]]'' series, the first novel that introduces Angelina gets like this. At first, [[LovableRogue Jim]] only wishes to catch her for his [[DaChief boss]] Inskipp. After all, it's not a very good idea to have a crazy murderess flying around in a giant battleship. After he foils her initial plot, she tries to kill him. He then gets a disguise and finds her again, running a con on another planet. While in this disguise, he starts to see a different side of her. He saves her from an assassin, and they end up spending the night together. She later reveals that she knew who he was but didn't care anymore. After some psychiatric help to remove her homicidal tendencies, they end up getting married (although it's literally a ShotgunWedding), thus the following novels no longer fit this trope.
* Tawnos and Ashnod from ''The Brothers' War'' (''TabletopGame/MagicTheGathering'') are in love, despite being generals on the opposing sides in a war.
* The only woman Literature/HerculePoirot comes close to being romantically involved with, is a highly skilled jewel thief.
* In ''Literature/TheThreeMusketeers'', d'Artagnan dates Milady for a while. And really, he is the one who lies to her. This is nothing to Athos, however, as he is still legally married to Milady by the time the book takes place.
* Literature/LymondChronicles ... Where to begin? There is the cringe-inducing tension between Lymond and ex-from-Hell Margaret. And his night with Joleta, where it is typically ambiguous who is seducing whom. ("There is such a thing as seducing in hate".) And perhaps Guzel.... And.... And....
* Literature/InheritanceCycle: [[spoiler: Nasuada and Murtagh. Their attraction sparks when Murtagh is a prisoner of her father, which blossoms into serious feelings when she's captured by his master Galbotorix.]]
* In Creator/AynRand's ''Literature/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.
* In Rand's ''Literature/AtlasShrugged'' the protagonist Dagny Taggart spends half the book searching for a man she calls "The Destroyer" and "The Most Dangerous Man Who Ever Lived", vowing to save the world from him. When she finally finds him (the famous John Galt), she falls in love with him at first sight, but still tries all she can to thwart him for another quarter of the book. (Rand's posthumously published Journals include a planned scene where she actually hands him over to the police and then bursts out crying when he is taken away; in the actual book, she only pretends to do it in order to save his life).
* In Creator/JackVance's ''Literature/{{Lyonesse}}'' trilogy, the protagonist Aillas falls in love with the haughty viking-like maiden Tatzel while being a slave at her father's castle. He escapes, comes back as a warrior king, kidnaps her and undergoes many adventures together with her, saving her life several times. Throughout he acts as the perfect gentleman, not taking advantage of his power over her. At one moment she actually offers him sexual favors in exchange for her liberty - but Aillas, wanting a love she is unwilling and unable to give him, declines the offer and sets her free anyway. Finally, when Aillas brings his army to assault the castle, Tatzel takes up a bow and arrow and dies among the last-ditch defenders. The victorious Aillas sadly refuses to look for "the body of the valiant maiden" among the scorched bodies in the ruins of the castle, and goes on to find another and more rewarding love.
* Almost every Franchise/SherlockHolmes work not by Creator/ArthurConanDoyle, from professional novels to amateur fanfics, has this crop up between Holmes and Irene Adler, to varying degrees of intensity and success.
* Occurs in the first two books of the ''Literature/ElementalAssassin'' between the protagonist Gin and Detective Donovan Caine. While he eventually loosens up on the fact that she killed his partner (Ultimately coming to the conclusion that if he'd known how dirty his partner was, he might have killed him himself), the basic fact that she's an assassin and he's a cop creates a conflict that they're never quite able to get over despite their mutual attraction, and Donovan ultimately removes himself from temptation by transferring to a different city.
* The novel ''Never Leave Me'' by Margaret Pemberton takes place in Nazi-occupied France, and its plot features a French girl who is active in the Resistance and a German Wehrmacht officer who fall deeply in love with each other. Much against both of their wills and in complete contradiction to the mutually-antagonistic national causes both of them serve, they are helpless to stop their intensive attraction to each other.
* Happens in ''[[Literature/TalesOfTheBranionRealm The Stone Prince]]'' in the middle of a battle, to the point where the man retires from combat to let his hormones settle before going after the woman again.
* The Committee of Public Safety of the [[PeoplesRepublicOfTyranny People's Republic of Haven]] in the ''Literature/HonorHarrington'' series of novels assigned {{Political Officer}}s to watch over its captains and admirals, as they were terrified the Navy might try a coup. While some People's Commissioners developed a wary sort of friendship with those they were theoretically supposed to ride herd on, most did their best to generally make their assigned captain/admiral's life a living hell. Unfortunately for the Committee, though, one of those commissioners and her admiral wound up falling quite desperately in love with each other. Though the two [[SecretRelationship maintained a facade of icy hostility in public]], as the commissioner in question was trusted implicitly by the Committee and thus could use her position to her own ends, behind closed doors was quite a different matter. In the end, [[spoiler:with the help of a few other key Navy personnel and their collaborative commissioners, they ended up overthrowing the committee and restoring the ''Republic'' of Haven]].
* Creator/CLMoore's ''Literature/JirelOfJoiry is a feudal warrior maiden. In the story "Black God's Kiss" Guillaume the Conqueror besieges and captures Jirel's castle after a prolonged fight, kills her retainers and captures Joiry herself. He tries to force a kiss upon her whereupon she sinks her teeth into his neck, barely missing the jugular, and later she escapes from the dungeon where she was held. Determined to find at all costs a way of destroying Guillaume, Jirel enters a dark underground world, braving countless dangers, monsters and perilous black magic. By kissing the statue of a sinister black god she gains the power of giving Guillaume a KissOfDeath, returns to the castle, kisses Guillaume and has the satisfaction of seeing him immediately die in great agony. Only when seeing him dead does she realize that she had been passionately in love with Guillaume all along and that now he is dead "the light had gone out of her world" - and she bursts out bitterly crying for the beloved enemy she had killed.
* In ''Literature/PleaseDontTellMyParentsImASupervillain'', the villain Lucyfar (who claims to be the [[{{Satan}} Archangel Lucifer]]) insists that she is dating the hero Gabriel (who she claims is the ArchangelGabriel). It's hard to tell if that's actually true or not. [[SheIsNotMyGirlfriend Gabriel says it isn't]], but he doesn't try too hard to get rid of her when she [[TheGlomp glomps]] him.
-->Rushing over to open it, Lucyfar squealed, "No time to talk about it. My date is here!" Seriously, she squealed. Who were the thirteen-year-olds here?\\
We filed out onto the rooftop after her as a mass of white wings fluttered down out of the sky. They tucked behind Gabriel's back as he landed, only slightly out of the way.\\
"So, you two are dating?" Claire asked pointedly, giving them both a hopefully questioning grin.\\
Her powers didn’t do her much good this time. "Yes!" Lucyfar declared immediately, throwing herself onto Gabriel and wrapping her arms around him.\\
"No," he contradicted, standing stiff and disapproving.\\
"Yes!" Lucyfar repeated, nodding like a bobble-head.\\
"No," Gabriel insisted, just like last time.
* In ''[[Literature/TheRiftwarCycle A Kingdom Besieged]]'', Jim Dasher (head of the Kingdom intelligence forces) and Franciezka Sorboz (his Roldemish counterpart) have been lovers occasionally, she's tried to kill him twice (for purely professional reasons) and as he puts it, "When you're not trying to kill me, there's no one I'd rather spend my time with".
[[/folder]]

[[folder:Live Action TV]]
* ''DarkAngel'' has Max and Logan meet after she steals his priceless Egyptian cat statue. He's the rich-hero-by-night ("eyes only") and she ends up helping him solve crime
* Mountie Fraser's doomed love affair with bank robber Victoria in ''Series/DueSouth'' is a [[DeconstructedTrope deconstruction]]. Turns out, it's really hard to have a healthy relationship with a bankrobber [[spoiler: and murderer]], especially if she has any hard feelings over you [[HonorBeforeReason putting her in prison after falling in love.]]
* Captain Picard and archaeologist/thief Vash in ''Series/StarTrekTheNextGeneration.'' Also, Captain Sisko and Kasidy Yates in ''[[Series/StarTrekDeepSpaceNine Deep Space Nine]]'' (Although the fact that Kasidy was a smuggler doing business with The Maquis was as swiftly ignored as it was tacked on). There's also Odo and the Female Changeling from ''[[Series/StarTrekDeepSpaceNine Deep Space Nine]]''.
* ''Series/TeenWolf'': Scott and Allison. A variation in which he ''knows'' she's on the opposing side, or, that her father is anyway- Also, starting season 3, Danny and [[spoiler: Alpha Twin]] Ethan in a homosexual and supporting character version of this.
* ''Series/WizardsOfWaverlyPlace'': Justin and Juliet.
* ''Series/XenaWarriorPrincess'': Xena and Ares.
* Jack and Nina from ''Series/TwentyFour''. Though all tension is gone from Jack's end and replaced with genuine hatred once [[spoiler: Nina kills his wife.]]
* ''Series/{{Smallville}}'', in the first of the three episodes Alicia appears in, the Clark/Alicia relationship is this trope. Afterwards, she's ReformedButRejected by all but Clark. And in Season 7, [[AntiHero Oliver]]/[[WellIntentionedExtremist Tess]], though they only dated before they became hero/villain, and besides one booty-call, nothing else happens.
* ''Series/BirdsOfPrey''. Helena/Reese had some overtones of this, especially in the first few episodes when he thought she was a criminal. Notably, Helena is the daughter of Batman and Catwoman in this continuity.
* ''Series/{{Nikita}}''. Michael and Nikita are on opposite sides, but used to work together. Sometimes it's subtext - their inability to kill each other - but sometimes not so much. By the end of the first season, [[spoiler:Michael's switched sides, so this trope no longer applies and they revert to being a BattleCouple]].
* Phoebe Halliwell and Cole Turner on ''Series/{{Charmed}}'', although initially he was just trying to seduce her so he could kill her, He eventually turned good [[HeelFaceRevolvingDoor for a while]].
* ''Series/{{Heroes}}'': Mohinder and Eden, Sylar and Elle (at least [[FaceHeelTurn at first]]), Matt and Daphne, Lydia and Samuel; it goes on forever, thanks to the show's HeelFaceRevolvingDoor.
* In ''Series/{{NCIS}}'' Ziva had a relationship with a crooked, alcoholic Mossad agent. It failed, spectacularly.
* In ''Series/StargateSG1'', Daniel Jackson met Vala Mal Doran when she attempted to steal the Earth ship ''Prometheus''. An undeniable attraction began soon after. In at least one timeline, they eventually got together before falling victim to a literal ResetButton.
** In a ''Series/{{Farscape}}'' connection; Aeryn Sun (also played by Claudia Black) tried to kill John Crichton (played by Ben Browder who'd go on to ''SG-1'' as well, where the fact that he and Jackson's actor Michael Shanks resemble each other was brought up a few times). They worked out their issues and eventually married and had a child.
* Helen Magnus and John Druitt of ''Series/{{Sanctuary}}''. They were engaged until Druitt [[spoiler: acquired an EnemyWithin and became JackTheRipper]]. Now he [[HeelFaceRevolvingDoor alternates between helping and tormenting Magnus]], but admits he still loves her. One episode implied she feels the same way.
* Nate and Sophie's pre-series relationship on ''Series/{{Leverage}}''...even though he remained faithful to his wife and she believes he was never ''really'' tempted.
* CJ and Danny from ''Series/TheWestWing'' are a mild version of this: she is the White House press secretary, he is the chief White House correspondent from the ''Washington Post''. Her loyalty is completely with the president and protecting him from his political enemies, and he refuses to neglect his duty to report accurately and to inform the public of as much as he can find out, two sets of interests which of course come into conflict quite frequently. They mainly have an up-and-down cycle of trying to date, pissing each other off, giving each other the cold shoulder, trying to date again, breaking up because of ethics worries, being unable to resist each other, deceiving each other again and fighting over it, ad infinitum.
** A rare happy ending is implied for this couple, as CJ quits politics despite an offer from incoming president Santos, to go run a much-less-controversial charity initiative.
* Jack and Juliet from ''Series/{{Lost}}''. They started to develop feelings for each other before Juliet's HeelFaceTurn. Then later, in the [[spoiler: 1970's time travel sequence]], Sawyer and Juliet. Although, by this time Juliet is a full Face and Sawyer's intentions are always questionable. You could also argue Kate and Sawyer considering Sawyer's HeelFaceRevolvingDoor.
* John Connor and Cameron in ''Series/TheSarahConnorChronicles''. He's the future savior of mankind, destined to save humanity from a race of machines. She ''is'' part of that race of machines, and originally programmed to assassinate him. Though reprogrammed to be one of the good guys, it doesn't always stick... Sexual tension ensues. And ''how''.
* Xev and [[{{Satan}} Prince]], ''{{Lexx}}''.
--> '''Prince:''' Do you still feel anything for me?
--> '''Xev:''' A little.
--> '''Prince:''' You shouldn't.
* ''PartyAnimals'': Ashika, a Tory MP candidate, and Scott, a lobbyist turned campaign manager for her Labour opponent. After a lot of UST, they do fall in love and sleep together [[spoiler: but at the end of the series she's convinced, wrongly but with good reason, that he's leaked the photos that cost her the seat.]]
* [[Series/BlakesSeven Servalan and Avon.]] The blatant flirting and occasional bouts of passionate kissing move this one out of the realms of [[FoeYay subtext]], but it's still not really a relationship because neither of them trusts the other any further than they could throw a cake underwater.
* Emma and Olly from ''Series/TheThickOfIt''. Well. He's working for the Secretary of State for Social Affairs and Citizenship, she's working for the shadow Dosac secretary. But then their bosses know about their relationship and his at least actively encourages it -just so Olly can leak policies to Emma, or know of hers. It also works the other way round. However, it's not clear that they actually even like each other...
* While they are not the lead characters in ''Series/{{Battlestar Galactica|Reimagined}}'', the relationship of [[spoiler:Captain Karl "Helo" Agathon and a Cylon copy of Lt. Sharon Valerii]] is suitably [[StarCrossedLovers star-crossed]]. [[note]] The original is codenamed Boomer, and the copy eventually adopts the codename Athena.[[/note]] And despite [[spoiler: the attempted gang-rape, demotions in rank, distrust, and Presidential baby-stealing, they are, as of the midpoint of season four, fairly happily married]].
** [[spoiler: Until Boomer shows up and impersonates Athena.... Despite his near death in the finale, they get a happily ever after.]]
* ''Series/BuffyTheVampireSlayer'':
** Buffy/Spike and, to a lesser extent, Buffy/Angel (the latter applies only when Angel actually [[FaceHeelTurn does something evil]], which doesn't happen a lot).
** The trope is deconstructed when Spike and Buffy get together in Season 6 -- the result is a DestructiveRomance, due to Buffy's self-loathing over the relationship and Spike's failure to understand Buffy's moral qualms.
** Most of Xander's love interests turn out to be demons. He even nearly married Anya, who created a universe in which Xander ''died twice'' during her first appearance.
** Not just Buffy either. Faith actually does Xander after several prods about whether Buffy has (not to mention she tries to rape him when he doesn't want to have sex with her), and she wants to know what Angel was like. She later tries to get into his pants counting on him going evil because of it (in her words, she intended to stretch out that 'moment of happiness' into a long weekend) before it becomes a strong, non sexual friendship during her HeelFaceTurn. And she teases Spike over what she or Buffy could do to him, then later they discuss sex and it's [[{{Jossed}} hinted they did it]].
** And there was one episode when Oz was into that other werewolf.
** Buffy actually wooed Count Dracula himself. She even attracted the attention of The Immortal, an Italian Lothario who had racked up quite a hit count in his own right; in this case, however, The Immortal was duped into dating an impostor.
* On ''Series/{{Angel}}'', Wesley and Lilah Morgan, whom he later beheaded. Angel/Eve. (Lorne made them do it!) Angel/Faith in season 4 and (arguably) Gwen Raiden.
* For all the animosity between them, ''Series/{{Firefly}}'s'' Mal and Saffron do manage to show a teensy, tiny bit of affection toward one another - when they aren't PistolWhipping each other or leaving the other party naked to die in the middle of a desert. And don't forget, they technically ''are'' [[AccidentalMarriage married]].
** Only if you don't count her flagrant bigamy -- who hasn't she married?
* Pops up in ''Series/{{Dollhouse}}'' with the brief interaction between Bennett Halverson and Topher Brink. Both of them are hammered hard by their various {{Geeky Turn On}}s even before they meet each other (Topher considers Bennett a supreme genius, and Bennett has a massive crush on Topher) and there's several adorable moments between them, including one where Topher ends up implying to Bennett without saying anything that he thinks she's beautiful, and has a ''priceless'' embarrassed reaction. In fact, Topher says she would have been perfect, [[spoiler: except for the fact that she's insane and wants to brutally torture and murder Echo for leaving her to die]]. Kinda kills the relationship....
** And yet somehow, they're back to flirting in her next appearance, until something even ''more'' drastic comes to kill their relationship.
* In ''Series/TheManFromUNCLE'', Napoleon Solo apparently has an ongoing flirtation with Angelique, an agent of THRUSH.
* [[BondageIsBad Gil Grissom and Lady Heather]] in ''Series/{{CSI}}''.
* Stuart and Jacqueline in ''[[YoungBlades 04 - The Exile]]''.
* [[EvilSorcerer Om]][[SmugSnake en]] of ''DarkOracle'', a recurring antagonist, nursed a fairly serious crush on Cally, one of the protagonists, throughout its run. Whether he was just using her initially is up in the air, although by the end he cared enough to [[spoiler: [[TakingTheBullet take a bullet]] for her]].
* ''Series/PowerRangersInSpace'': Zhane the Silver Ranger with Astronema. Yes, the ''main'' antagonist. The romance lasts just one episode, spoiled by another battle. Later on after the [[spoiler:[[LukeIAmYourFather Luke, I Am Your Sister]]]] reveal, Andros the Red Ranger invokes [[spoiler:MySisterIsOffLimits]] retroactively.
** ''Series/PowerRangersTimeForce'' has another one-episode version: Lucas the Blue Ranger is a ladies' man, and Nadira falls for him after she discovers some love poetry he's written. This is unfortunately one-sided, as she's DaddysLittleVillain and said Daddy Ransik is an OverprotectiveDad; after Ransik puts Lucas through some TwerpSweating he panics and starts going "PleaseDumpMe!" By the way, that poetry that Lucas wrote was actually for [[spoiler:his car]]. They do seem to get together post-season, though, once Nadira and Ransik have both made {{Heel Face Turn}}s.
** In ''Series/PowerRangersNinjaStorm'' Dustin with Marah, but she ends up betraying him after considering a HeelFaceTurn. When she and her sister bail on Lothor for real at the end of the series, she's quick to ask Cam if Dustin still has a crush on her. Cam says they can talk about once they're out of the exploding spaceship.
** There are shades of this in ''Series/PowerRangersDinoThunder'', with Tommy sharing an attraction with Principal Randall... who is really [[TheDragon Elsa]] in disguise.
* Downplayed in ''Series/BabylonFive'', where Vir Cotto helps Narns escape the Centauri occupation while his [[TheDitz ditzy]] [[ArrangedMarriage fiancee]] Lyndisty fondly remembers killing entire villages. Vir was less than thrilled with the setup; and [[WhatHappenedToTheMouse Lyndisty is never heard from again after the single episode in which she appears]].
* By series 6 of ''Series/DoctorWho'', the Doctor became romantically involved with a convicted murderer and psychopath raised to assassinate him. [[spoiler: She succeeds more than once,]] but he keeps coming back for more. (Averted, though, in that very early on in their relationship ([[TimeyWimeyBall from her perspective]]) she changes allegiances completely, and her loyalty is absolutely and without question with the Doctor from there on out.)
* Gary and Anna ''Series/{{Alphas}}'', though neither of them have any real contempt for each other, and are more close friends than anything else.
* Jack Bristow and Irina Derevko on ''Series/{{Alias}}''. Even though she was a KGB sleeper agent who posed as his wife and constantly walked through the HeelFaceRevolvingDoor, they clearly wanted to debrief each other quite badly.
** Complicated by the very real betrayals on Irina's part, not just the original swallow mission, but ''multiple'' subsequent betrayals of both her 'husband' and their daughter. Her attraction to Jack is clear... unfortunately, neither her love for Jack nor her daughter [[spoiler: either of them, for that matter]] could overcome her addiction to Rambaldi's work.
* Kono's mystery boyfriend on ''Series/HawaiiFive0'' has turned out to be Adam Noshimura, the heir to Honolulu's {{yakuza}} clan. Admittedly he's trying to turn their operations legit, but he's not finished yet.
* ''Series/{{Dexter}}''
** Dexter and Lila in season 2. It says something when Dexter is a serial killer and the girl he dates is darker than him.
** Dexter and Hanna [=McKay=] in season 7.
* ''Series/{{Scandal}}'': The beginning of Quinn's romantic relationship with Gideon, a cub reporter who seems on the verge of breaking the Amanda Tanner story.
** [[spoiler: An especially tragic end, as Gideon dies and Quinn is effectively framed for the murder.]]
* In ''Series/{{Vegas|2012}}'' there's a definite attraction between Jack Lamb and Mia Rizzo from about the second episode, and the two end up in bed at the ChristmasEpisode and secretly dating after. The one is the younger brother of Sheriff Ralph Lamb and his right-hand both on the ranch and in the squadroom, and the other is a senior finances manager at a mob-run casino and the daughter of a made man.
* Damon and Elena from ''Series/TheVampireDiaries''. Both in the series, and the books.
* ''Series/{{Supernatural}}'': Most times where a villain takes an interest in one of the heroes it's just unidirectional FoeYay. There are some cases where the heroic one reciprocates, though.
** Sam Winchester (a hunter of supernatural monsters) and Ruby (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 [[PsychoSerum which he is addicted]]. When he admits it to Dean, his brother is more than squicked out.
** Castiel and Meg share a lot of sexual tension before they make out, and later express their love for each other. An angel and a demon, how poetic.
* [[spoiler:Sherlock and 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.]]
* Weird example. In the ''Series/StarTrekDeepSpaceNine'' episode "Our Man Bashir", Bashir's ''character'' in a holodeck scenario, a Franchise/JamesBond {{expy}}, is in a relationship with a female KGB agent.
[[/folder]]

[[folder:Music]]
* Music/{{Blondie}}'s "X Offender" is about a prostitute who falls in love with the police officer who busts her.
* In the rock/metal opera project ''Aina: Days of Riding Doom'', Syrius and Orianna fall deeply in love, despite being commanders of opposing sides in the war. [[{{Squick}} And half-brother and half-sister.]] Not that they know it, to be fair.
* Kirby Krackle's song "Then Again, Maybe Not" is sung from the point of view of a superhero who is a little tired of fighting his arch-nemesis, and suggesting that grabbing some Mexican food and flirty conversation would be a better idea.
[[/folder]]

[[folder:Newspaper Comics]]
* [[ComicStrip/KrazyKat Krazy Kat and Ignatz Mouse]] [[FriendlyEnemy refer to each other as enemies]], but Krazy is [[MadLove madly in love with Ignatz and harbors the delusion that he returns these feelings]]. This is made more complicated by [[FoeYay occasional hints that]] [[TheCuckoolanderWasRight this might not really be a delusion]].
[[/folder]]

[[folder:Tabletop Games]]
* ''TabletopGame/{{Nobilis}}'': Nobles have shacked up with Excrucians on grounds ranging from "[[TrueArtSticksItToTheMan screw Lord Entropy]], LoveRedeems" to "someone told me not to". One RunningGag in third edition is that Jenna Moran (author) and Miranda Harrell (one of the artists) have...''[[WillTheyOrWontThey ambiguous]]'' relationships with the Excrucians Genseric Dace and Coriander Hasp, respectively.
[[/folder]]

[[folder:Video Games]]
* The Trope Namers Batman & Catwoman are at it again in BatmanArkhamCity, providing the trope page.
* Franchise/SlyCooper and Carmelita Fox. He's a heroic GentlemanThief, she's a dedicated police officer. It's kind of one-sided to start with, but she softens up in the climax of each game, then gets really angry when Sly slips away.
** At least until [[VideoGame/Sly3HonorAmongThieves the third game]], where they actually hook up for good at the end. Sly willingly gives up his life of crime and all of his friends, saves her life, and fakes a convincing amnesia act to let her justify it. [[spoiler: Then in [[VideoGame/SlyCooperThievesInTime the next game]], it's back to business. Sort of.]]
* Turns out that your love interest in ''VideoGame/QuestForGloryIV'' is [[spoiler: a powerful vampire known as The Dark Master who wants to resurrect the local EldritchAbomination.]]
* The situation with Silk Fox and the player ([[BiTheWay either gender]]) in ''VideoGame/JadeEmpire'' starts out looking like this, before a variety of revelations related to the GambitPileup point out that she is most definitely a good guy.
* Knuckles and Rouge from ''Franchise/SonicTheHedgehog'' fit this trope very nicely, especially in ''Anime/SonicX''.
* Alex, the only real LoveInterest in ''VideoGame/TheBastardOfKosigan'' 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.
* In ''VideoGame/HarvestMoon - Magical Melody'' you can marry your rival, Jamie, who is always the [[AmbiguousGender opposite gender]] from you. Considering that in the original Japanese, there were [[ExecutiveMeddling rival marriages]] much like most of the rest of the series for all the other bachelor(ettes), you and your rival are the true pairing. Sadly, however, your game ends if you marry them, and you can't even [[GottaCatchEmAll find all the magical notes]].
** ''VideoGame/HarvestMoon DS Cute'' also provided the option of marrying GentlemanThief Skye.
* [=MegaMan=] Volnutt and [[{{Pirate}} Tron Bonne]] in ''VideoGame/MegaManLegends''.
* Leon Kennedy and [[FemmeFatale Ada Wong]] of the ''Franchise/ResidentEvil'' series alternate between teaming up and pointing weapons at each other. All while oozing so much UnresolvedSexualTension into the air that it could be cut with the proverbial knife.
* In ''Franchise/AssassinsCreed'', the Assassin Altair and the Templar Maria end up falling in love, despite being enemies. This is shown in ''VideoGame/AssassinsCreedII'', where Desmond even has a memory of their child being conceived, and Altair's Codex contains a hand-drawn portrait of her.
** Worth noting that Maria actually [[HeelFaceTurn switched allegiances]] in ''Assassin's Creed: Bloodlines'', and canonically the romance came afterwards.
* Otacon and Sniper Wolf in ''VideoGame/MetalGearSolid''. [[AllLoveIsUnrequited One-sided from him to her]].
* The Warden and Morrigan in ''VideoGame/DragonAgeOrigins''.
** A Female Mage!Warden and ex-Templar Alistair.
* Mage!Hawke and Fenris, or Templar-aligned Hawke and Anders or Merrill in ''VideoGame/DragonAgeII''.
** The ShipTease between Templar!Carver and Merrill, as well as Circle!Bethany and Sebastian Vael.
* Garen and Katarina in ''VideoGame/LeagueOfLegends'', who quite literally got matched via a dating service, yet are champions of opposing countries.
** They are NotSoDifferent not just personality-wise but in gameplay, being two of the three champions that operate solely on {{Cooldown}}s with no ManaMeter, and having signature moves that involve [[EverythingsBetterWithSpinning lots of spinning]].
* Commander Shepard (Alliance) and Miranda Lawson (Cerberus) in ''VideoGame/MassEffect2''.
** All but outright stated between Aria T'Loak and Nyreen Kandros in the third game's Omega DLC. Aria is the cold-blooded ex-merc whose word is law on her WretchedHive, Nyreen's ex-turian military and always thinks about the little people ("she oozes virtue"). It ended when they realized it couldn't work unless one of them changed, and Nyreen didn't want that to be her.
* In ''VideoGame/TheElderScrollsVSkyrim'', the ''Dawnguard DLC'' has a subtle ShipTease between [[FriendlyNeighbourhoodVampire Serana]] of the [[SupernaturalElite Volkihar Vampire Clan]] and the Dragonborn, even if the latter chooses to remain aligned with the [[VampireHunter Dawnguard]].
[[/folder]]

[[folder:Visual Novels]]
* [[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.]]
* ''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]]

[[folder:Web Comics]]
* Webcomic/EvilInc.: [[spoiler:Captain Heroic]] and [[spoiler:Miss Match]]. There was also an affair between [[spoiler:Commander Heroic]] and [[spoiler:Flame]] long ago, and lately [[spoiler:Lightning Lady]] and [[spoiler:Elastic Man]] have developed a relationship.
* ''Webcomic/RipHaywire'', with Rip and Cobra.
* [[Webcomic/CiemWebcomicSeries Denny Levens]] was a retired inventions supplier for the mob. When he learned that the Hebbleskin Gang was behind some purchases, he got out of the business. His past hobbies don't make him a threat to Candi directly; but the fact that she marries a Hebbleskin deserter makes her enemies want her dead [[UpToEleven even more]].
* ''Webcomic/GirlGenius'':
** Baron Klaus Wulfenbach has canonical amorous history with Lucrezia Mongfish [[spoiler:a.k.a. the Other]]. That's pretty solidly in the past, though; she's used creepily familiar terminology and physicality, but he was ''clearly'' not responding and anyway she does that to everyone.
** The Baron's son Gilgamesh and main heroine Agatha Heterodyne, with the dramatic twist that though they're both noble and heroic, circumstances keep putting them on the opposite side. And it was about four (real-life, not [[WebcomicTime webcomic]]) years between their scenes together. ''Damn you, Foglios!''
* ''Webcomic/UmlautHouse'': [[spoiler:Liz and Dr. Sappho]], Eliza and Dr. Sisyphus.
* In ''Webcomic/CaseyAndAndy'', Jenn has been crushing on Quantum Cop for ages, and it turned out that her feelings were reciprocated (just in case their time-traveling daughter from the future wasn't proof enough..) Complicating their relationship is that he is ''literally'' The Perfect Cop, while she's an International Jewel Thief. [[http://galactanet.com/comic/view.php?strip=650 He doesn't seem to mind much, though.]]
** The reader doesn't find out that Jenn is a crook until nearly the end of the strip, although Quantum Cop figured it out years earlier. The author did plant clues for a really long time.
* Early on in ''Webcomic/SluggyFreelance'' Torg has this situation when he develops a crush on Val, who is revealed to be [[spoiler:a vampire. Torg inevitably has to kill her]].
** And then there was his promise to marry [[AxCrazy Oasis]]...a promise he intended to keep. (One only wonders how [[spoiler:Zoe's death]] will affect that...)
* In ''Webcomic/{{Erfworld}}'', Wanda and Jillian arguably had such a relationship at one point.
** It must be said the Wanda was simply using magic to manipulate Jillian into being her unwitting servant.
*** Their [[MoreThanMindControl relationship]] was...[[{{Fetish}} complex]].
**** Nor was it unwilling either...
* In ''Webcomic/EverydayHeroes'', Jane and Mr. Mighty [[http://www.webcomicsnation.com/eddurd/everydayheroes/series.php?view=single&ID=138013 first met each other]] when he was guarding a house that she and her partners were trying to rob. She tried to ambush him from behind; since he's invulnerable and she's not, [[AgonyOfTheFeet this didn't work well]].
* ''Webcomic/TheOrderOfTheStick'':
** Deconstructed with [[TheFettered Durkon]] and [[TheHedonist Hilgya]]. They were attracted to each other, and seemed to be coasting towards a RelationshipUpgrade, but their differences in alignment proved irreconcilable. Another problem was that Hilgya was technically still married to someone else Their breakup was considered the series' first major TearJerker
** Elan and Therkla, though it was incompletely requited (Elan is mostly devoted to Haley).
** Roy and Miko were canonically attracted to each other at different points, and [[WordOfGod the author had originally intended them to be love interests]], but quickly realized that it wasn't happening.
* In ''Webcomic/TheAdventuresOfDrMcNinja'', Dr. [=McNinja=] and Hortense. They used to be dating, but broke up... then meet up again where she's trying to stop Doc from saving the world. [[spoiler: Of course, it turns out to be Doc's parents trying to get the two back together.]] Later, she's revealed to be working with [[spoiler: King Radical]], but there's still some romantic tension between the two.
* ''Webcomic/SuperStupor'' [[http://www.superstupor.com/sust01022008.shtml demonstrates]] this one played pretty straight...except that it's the ''morning after''.
* ''Webcomic/BobTheAngryFlower'' once went out of his way to hunt a beautiful international diamond thief just so he could ask her out. Their relationship turned out to be a lot less hot than most on this page.
* ''Webcomic/{{Lightbringer}}'', a web comic by [[WebVideo/AtopTheFourthWall Linkara]], gives us the issue [[http://lightbringer.comicgenesis.com/d/20081112.html Masks]], where Lightbringer's girlfriend Sandy is revealed to be the the Scarlet Baroness, who's BreakingSpeech on SecretIdentityIdentity throws [[TheCape Lightbringer]] off guard and forces his sidekick into pulling a GetAHoldOfYourselfMan.
* In Webcomic/DubiousCompany, [[DarkChick Mary]] thinks she is this with [[TheChick Elly]]. Elly highly [[AllergicToLove disagrees]].
* ''Webcomic/QuestionableContent'' has Marigold and Dale, who play on opposing sides in ''VideoGame/WorldOfWarcraft''.
* In ''Webcomic/JetDream'', Harmony Thunder ([[GenderBender back when she was Jack Thunder]]) had this type of relationship with the mercenary Raven Red. Harmony's sex change [[IfICantHaveYou puts further strain on the relationship]].
* ''ComicStrip/WhatsNewWithPhilAndDixie'' once [[http://www.airshipentertainment.com/growfcomic.php?date=20081109 explored]] this in ''TabletopGame/MagicTheGathering''-based soap opera comic.
[[/folder]]

[[folder:Web Original]]
* One of ''ShadowOfTheTemplar'''s main plots is the developing relationship between FBI agent Simon Drake and GentlemanThief Jeremy Archer.
* The Rocket of ''Literature/LegionOfNothing'' wooed Ghostwoman during WWII, when he was fighting for the US and she was a Nazi Superspy. Unsurprisingly, this was the topic of the first [=LoN=] fan-fic.
* Los Hermanos, a member of the {{Global Guardians|PBEMUniverse}} is having a torrid affair with Brigit, the daughter of [[DiabolicalMastermind Lord Doom]] via one of his copy bodies.
* In ''Literature/ChaosFighters II-Cyberion Strike'', [[spoiler:Etliz, a wanted criminal and Etlisk, one of the police officers tasked to ''catch her and her comrades'']] go as far as ''an actual date'' after [[spoiler:Etliz was saved from getting naked when Etlisk put a final blow which stops clothing damage on her.]] a subversion occurs when she pulls a HeelFaceTurn later on.
* According to their actors, WebVideo/TheNostalgiaChick and WebVideo/TheNostalgiaCritic. Neither of them are heroes or villains in the traditional sense, but their FoeYay and NotSoDifferent-ness are off the charts.
* In ''WebVideo/TheGuild'', Codex finds herself getting intimately involved with the leader of her guild's villainous rivals.
* Eric had sex with Sister in [[Roleplay/MallFight Mall Fight 3]], and remains on good terms with her. As much as one can be with [[AxCrazy Sister]].
* In ''Literature/TalesOfWyre'', [[spoiler:[[ThePaladin Eadric]]]] becomes involved with [[spoiler:[[DemonLordsAndArchDevils Soneillon]]]].
[[/folder]]

[[folder:Western Animation]]
* In an episode of ''WesternAnimation/BatmanBeyond'', Terry [=McGinnis=] meets and starts to fall for a girl...who turned out to be Ten of the Royal Flush Gang. As the gang is arrested, Terry asks Bruce, "this kinda thing ever happen to you?" Bruce smiles. "[[ContinuityNod Let tell me you about a woman named Selina Kyle...]]" Eventually the girl leaves her family's gang and gets a regular job and lifestyle, unfortunately she had betrayed Terry ''and'' Batman's trust once again before going straight, and Terry wasn't interested in leaving his steady girlfriend for her. As a conciliatory note, the end of the episode reveals that her actions convinced her brother to leave the gang as well so she's not entirely alone.
* Danny and Valerie on ''WesternAnimation/DannyPhantom.'' Although in this case, only he realized it; Valerie didn't find out Danny's secret identity until the GrandFinale, long after their relationship ended (ironically, for ItsNotYouItsMyEnemies reasons).
* Parodied on ''WesternAnimation/TheSimpsons'', when Bart has a Radioactive Man comic book in which the hero marries "Larva Girl". The issue's title is "To betroth a foe!"
* [[HeelFaceTurn Until she eventually converted to his side]], Blackarachnia and Silverbolt had this kind of relationship in ''Franchise/{{Transformers}}: WesternAnimation/BeastWars''. True, she was originally a Maximal converted to the enemy's side via {{Brainwash|ed}}ing, but still...
-->'''Blackarachnia''': I like being a bad girl. And you know something else? Somewhere deep beneath this squeaky clean armor-plating of yours, I think you like it too, hmm?
** For double points, they had this relationship in the sequel series as well. but in reverse: Silverbolt's spark was in one of their foes and Blackarachnia was determined to convert him as he had converted her.
** To bring Blackarachnia into ''WesternAnimation/TransformersAnimated'', she became Optimus Prime's Catwoman. That is, once she gets over [[NoOneGetsLeftBehind getting left behind]].
* Jake and Rose on ''WesternAnimation/AmericanDragonJakeLong''. Before Rose learned of Jake's SecretIdentity, she was also his [[LovesMyAlterEgo Lois Lane]] and his GirlNextDoor.
* WesternAnimation/AeonFlux and Trevor Goodchild, of course. Though which of these is the villain is debatable.
* In ''WesternAnimation/{{X-Men Evolution}}'', Kitty/Shadowcat of the X-Men and Lance/Avalanche of the Brotherhood of Evil Mutants got together during the second season, though unlike most cases the villain in question was acting much more noble than previously, and the relationship led to a considerable amount of character development for him later.
* Keeping on the X-Men theme, ''WesternAnimation/{{Wolverine and the X-Men}}'' does this with Nightcrawler and the ScarletWitch. However the relationship between them is difficult to define. Kurt cares about her and tries to steer her on the right path, yet never openly admits he cares about her as anything more then a friend. Wanda herself does love Kurt and it's admitted as such, but its hard trying to date an X-Man when your father's ideology directly opposes theirs. Wanda throughout the first season struggles between the loyalty to her father and her crush on Kurt; [[spoiler: in the end Nightcrawler's charm finally seeps through and she rejects her father partly because of Kurt's influence, mostly because he was willing to sacrifice other mutants to achieve his ultimate goal.]] Before anyone thinks this is completely out of the blue, there is actually a universe in the Marvel Multiverse where Kurt and Wanda did get together and they have a girl named Nocturne. Still, it's kind of a stretch nonetheless.
** Not the biggest stretch when considers that Nightcrawler has often been portrayed as having a strange ability to attract women like flies to a bug lamp. In one of his miniseries Beast even notes that he's jealous since there both blue, furry, and look like demons yet he can't get a girl and Kurt, at the time, had three girls after him.
** Hey, what can Kurt say? [[WesternAnimation/{{X-Men Evolution}} Chicks dig the fuzzy dude.]]
* [[IdiotHero Dave]] and [[TheVamp Princess Irmaplotz]] in ''WesternAnimation/DaveTheBarbarian''.
* ''WesternAnimation/TheVentureBrothers'' has murder machines extraordinaire Brock Samson and Molotov Cocktease back when they were both secret agents.
** Rusty tries to invoke this with Dr Girlfriend, but she isn't interested.
*** Dr Girlfriend attempts to invoke this on Brock, he's not interested (He think she's a post-ops transsexual).
** Dr. Orpheus also wants to get in on this trope. When lobbying for his own archenemy, he requests an attractive redhead to maximize the possibility of {{UST}}.
* ''WesternAnimation/SpyGroove''. Spy #1 finds himself falling for Sierra Nevada, who's brilliant, gorgeous and evil.
* The old Sunbow ''Franchise/GIJoe'' series had an episode with Joe computer specialist Mainframe falling in love with Dreadnok Zarana while the latter was undercover infiltrating GI Joe headquarters. In a rare example of continuity, this relationship became significant in a later episode.
* In ''WesternAnimation/{{COPS}}'', COP Sgt. Mace and cat-burglar Nightshade had a romantic relationship despite being on opposite sides of the law.
* ''WesternAnimation/TeenTitans'': Cyborg starts dating Jinx when he goes undercover at the HIVE Academy, although it's the flirtatious Kid Flash who starts Jinx down the road to her HeelFaceTurn.
* ''WesternAnimation/ElTigre'' featured the titular character and [[DarkActionGirl Black Cuervo]]. The two dated twice, though they did so for their own personal reasons. Whereas Manny Rivera/El Tigre became disenchanted with her when he discovered she was just using him, Black Cuervo in turn developed a hopeless crush on him. Matters are made worse when Manny's best friend, [[GenkiGirl Frida Suárez]], is rivals (and not of the friendly kind) with Black Cuervo's [[SecretIdentity civilian persona]] Zoe Aves... with whom Manny seems to get along fine. Cue LoveTriangle.
** As a bonus, Black Cuervo's mother and grandmother (Voltura and Lady Gobbler) have had their own failed relationships with El Tigre's dad and grandfather (White Pantera and Puma Loco) in the past. GenerationXerox played straight.
* ''WesternAnimation/JusticeLeague'': In one episode while he's being held prisoner by the Injustice League, one of Batman's moves to disrupt their unity is to seduce Cheetah...What ''is'' it with Bruce Wayne and cats, anyway?
** A hint is dropped at the end of ''Unlimited'''s series finale, when Giganta turns to kiss Flash before [[MercyLead running away like the rest of the surviving villains.]]
*** This plot thread was carried over to the official tie-in comic, where she faked a HeelFaceTurn in order to woo the Flash, who simply thought she had legitimately reformed. After finding out that Flash had a date with reporter Linda Park, Giganta gave up the charade and tried to kill them both.
* ''WesternAnimation/DarkwingDuck'' had the hero falling for 'evil businesswoman' Morgana, though she easily Heel Face Turned for both of the schemes she was in on because she felt the same way. She even knew his secret identity by season three.
* On ''WesternAnimation/WordGirl,'' kid villain [[InsufferableGenius Tobey]] is rather explicit about his crush on the titular superheroine. She continually rebuffs him, though reluctantly admits she enjoyed herself when he once tricked her into spending the day with him.
* On ''WesternAnimation/TheGrimAdventuresOfBillyAndMandy,'' paranormal exterminator Hoss Delgado winds up dating Eris, goddess of chaos.
* Rex and Circe from ''WesternAnimation/GeneratorRex''. And [[DeconstructedTrope both are finding out the hard way just how much heartache it can cause.]]
** Breach kind of forces her way into this trope with Rex.
* ''WesternAnimation/BatmanTheBraveAndTheBold''
** Naturally has this between Batman and Catwoman in several episodes. One even has them become a crimefighting team, having a child, retiring and finally dying together. However, [[spoiler:it was all just a book written by Alfred]].
** Talia al-Ghul is depicted as a teenager in this version. Robin flirts with her in her first appearance, but she shoots him down. In her next she frees Batman from a DeathTrap, and when he asks why, [[PrecociousCrush she kisses him]]. [[DullSurprise He takes it stoically]]. "I see."
** One episode also has ComicBook/JonahHex hooking up with Lashina, depicted here as a henchwoman of Mongul and Mongal.
* In ''WesternAnimation/SupermanTheAnimatedSeries'' brainwashed Superman and Lashina of the Female Furies.
* On ''WesternAnimation/{{Archer}}'', Mallory Archer, head of ISIS, has been having an affair with Nikolai Jakov, head of the KGB, for forty years, going all the way back to their field agent days.
* In ''WesternAnimation/KryptoTheSuperdog'', the whole Batman/Catwoman thing even extends to their respective pets, [[InterspeciesRomance Ace the Bathound and Isis the cat]].
* ''WesternAnimation/YoungJustice'' has Red Arrow and Cheshire, just like the comics. After some one-sided flirting in the first season, they get married during the five-year TimeSkip, only to split due to Arrow's obsession with [[spoiler: finding the original Roy Harper]]. When Cheshire reveals they have a daughter, they get back together and have now reached BattleCouple status, complete with Cheshire carrying baby Lian around in a papoose while they kick ass. Both mother and daughter love it.
* ''WesternAnimation/TheSpectacularSpiderMan'' has the usual heavy flirting (and one kiss) between Spider-Man and [[BadassNormal Black Cat]]. However, they part on less friendly terms after [[spoiler:she blames him for her father, who is Uncle Ben's killer, refusing to break out of jail]].
* Offered in ''[[TronUprising TRON: Uprising]]''. Impressed with how Beck (in his normal guise) managed to deal with an incident involving a RunawayTrain, Paige suggests Beck look her up when they get back to Argon in order to "hang out", which Beck doesn't refuse. And this is on top of the {{Foe Yay}} the pair already have going on...
* Variation with Vanessa Doofenshmirtz and Monty Monogram from ''{{WesternAnimation/Phineas And Ferb}}''. It's really their dads that are on opposite sides, but they have to keep it secret anyway.
* While not exactly a "hero", Professor Farnsworth of ''WesternAnimation/{{Futurama}}'' has some history with [[CorruptCorporateExecutive Mom]], which resurfaces in a few episodes.
* In ''WesternAnimation/KungFuPandaLegendsOfAwesomeness'' One episode, Shifu's old flame Mei Ling comes to visit whom he dumped in their youth because she was a conniving thief. She tries to get back together but he refuses. [[spoiler: finally when he does start to feel for her she uses a mystical stone to swap bodies so disguised as Shifu she would trick Po and the Furious Five into robbing a vault for her. In the end after everything is back to normal, Shifu sends her to prison. Which she escapes before arriving and runs off somewhere.]] The ending implies Shifu still having feelings towards for her.
** Also there was an episode where Po's father feeling betrayed and unappreciated starts dating Scorpion (A recurring villain, since he doesn't pay attention or seem to even care about Po's Kung-Fu life so he knows nothing of the enemies on the show) though [[spoiler: Scorpion was only getting close to him since he was catering a festival which she planned to poison the entire valley.]]
[[/folder]]

[[folder:Real Life]]
* Neither person was ''evil'', but American political strategists Mary Matalin (a Republican, and quite conservative) and [[RaginCajun James Carville]] (a Democrat, and liberal enough) faced each other across several elections in TheEighties, culminating in the 1992 campaign (in which Carville engineered BillClinton's winning strategy), still regularly appear across from one another on political debate shows, and call one another [[ArchEnemy arch-enemies]]. They not only dated, but are ''married'' (getting hitched in 1993) and the proud parents of two daughters. They understandably do not talk politics at home.
* Rival {{NASCAR}} racers Danica Patrick and Ricky Stenhouse Jr. announced they were dating while both were competing for the 2013 NASCAR Rookie of the Year Award.

[[/folder]]
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