Dating Catwoman



""We conducted our courtship on rooftops and fire escapes. A strange flirtation, a hide and seek, a game of cat and mouse...""

- Catwoman, Whatever Happened to the Caped Crusader?

When the hero of the show and one of the antagonists have a romantic tone, either as subtext, or, less commonly, right out in the open. This allows a degree of tension into the relationship, and as long as you make sure the antagonist is less of a "villain", we're allowed to root for them.

Their slightly different senses of morality will conveniently keep things from progressing too quickly out of the writers' grasps; and sometimes they won't move much at all, since the character may not be as fun if they go straight. The same concerns about getting rid of the dramatic tension that fuel Will They or Won't They? apply here.

Compare Go-Karting with Bowser, Loves My Alter Ego, or Capulet Counterpart. Almost always a part of Villainesses Want Heroes. May lead to The Masquerade Will Kill Your Dating Life if the pairing is ultimately incompatible or too unstable. The one-sided version of this may be a Villainous Crush. See Foe Yay for the less explicit version of this, and Fatal Attraction when it's more dangerous.

Has nothing to do with dating a Catgirl. Usually.

Anime and Manga
"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."
 * Kaitou Saint Tail and Asuka Jr.; in this case, the lead, a Phantom Thief that steals back stolen items, is the Catwoman-ish one.
 * Since Kamikaze Kaitou Jeanne is heavily inspired by Kaitou Saint Tail, Jeanne also has a romance with her main rival,.
 * Jeanne and Chiaki were justified in the manga:.
 * 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 Tokyo Mew Mew, where the romantic hero and villain are... a Genki Girl and a Bratty Half-Pint, each the "annoying kid" of their team.
 * Dokkoida?! combines this with the Unwanted Harem; the male superhero, his (female) Rival, and all the supervillains (who are almost all female) all live in the same apartment building and hang out together when disguised as Muggles.
 * In UFO Robo Grendizer -one of the Mazinger Z sequels-, Duke They loved each other. However he did not think they could be together again after what the Vegans had done to his homeworld.
 * Aimi/Shadow Lady and Bright in the manga Shadow Lady.
 * Dragon Ball 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 The Starscream to the previous Big Bad Vegeta. Interesting in that a time traveller tells the hero this will happen before it does, which knocks him on his ass. The second instance is Krillin, who falls in love with former 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 Heel Face Turn (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 Special Duty Combat Unit Shinesman, Matsumoto, a young businessman who is 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
 * This is largely the point of the romance between the primary Official Couple in Wedding Peach, who are directly inspired by Romeo and Juliet which would make them fit the Star-Crossed Lovers trope but luckily.
 * Team Chef Sai Saici and Plucky Girl Cécile (the sister of Gundam Fighter Hans Holgar) in G Gundam. Causes less problems than most examples, since Hans is no mortal enemy, but a decent, friendly Worthy Opponent in a sports tournament.
 * Happens in Red Garden when Kate ends up dating . She's oblivious about his real role in things, but he knows hers from the very start.
 * Gundam ZZ has an unusual situation wherein the Lady of War Big Bad, Haman Karn, grows attracted the 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. Judging by how the ladies get interested in him...
 * 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 Project ARMS, although it seems to be mostly one-sided..
 * Ruby and Courtney from Pokémon Special 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 Magical Girl Lyrical Nanoha. Despite being 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 that the rare descendant who would inherit his traits could feel it over the centuries.
 * Bizarre example in The Lucifer and Biscuit Hammer, where the two people are technically on the same side at the present due to an Enemy Mine, but nevertheless one wants to destroy the world and the other wants to save it.


 * By the end of the series,
 * Rangiku isn't the main character of Bleach, but she's pretty much in love with Gin, her childhood friend who is following Aizen, the main antagonist of the series.
 * Umineko no Naku Koro ni has Battler and Beatrice, whose romantic undertones are there, but not quite strong or obvious. However, in the end, it turns out that  Possibly subverted, since Beatrice is
 * 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).
 * Sai and Baby-5 from One Piece; while the terms "hero" and "villain" are subjective here for both of them, they were enemies when they met during the Dressrosa Arc, until after misinterpreting his threats as romantic pick-up lines, she fell in love with him. Eventually, Sai challenged Lao-G to defend Baby-5's honor, promising to marry her if he won; he did, and as of the end of that Arc, are Happily Married.

Comic Books

 * Naturally, the Trope Namer and most famous example is the romantic tension between Catwoman and Batman. The Earth-2 versions of the characters actually married and had a kid, the original Huntress. 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 have gone a bit more interesting with the two since - 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 Character Development in their relationship was set back to square one with the 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.
 * Funnily enough, the whole 'dating Catwoman' trait stems from the fact that Batman himself has a weakness for villainesses, which he acknowledged in Batman R.I.P. His relationship with Talia al Ghul in the main continuity (where they have a son together) is similar to his relationship with Catwoman. In Gotham City Sirens, it was mentioned that Catwoman and Talia are probably the only two women Batman has truly loved.
 * Very explicit in one standalone strip called "Date Night", where Batman catches Catwoman in the middle of a robbery and chases her through various romantic locations - including a flower stall and a fancy restaurant, with Catwoman talking and flirting with him as if they were actually on a date all the while. 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.
 * Zigzagged with Harley Quinn; while she doesn't show any affection to Batman past the occasional flirting, she was briefly intimate with Bruce Wayne in one New 52 story.
 * 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.
 * Though that particular possibility has now been reopened, due to a recent (and much-hated) Cosmic Retcon. 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.
 * Captain America 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...)
 * Iron Man and Madame Masque/Whitney Frost. Then again, it's not surprising considering the number of paramours Tony's had over the years. It came to the point where Frost 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 Black Widow, a former enemy.
 * And Masque hooked up with The Hood.
 * Captain Atom wound up marrying Plastique, a former Quebecois terrorist with explosive powers. Appropriately, in Justice League Unlimited she.
 * Silver Age Marvel Comics tended to see this pop up a great deal with heroines and manly-man opponents—e.g. the Fantastic 4's Sue Storm to the Sub-Mariner (while he was a functional villain), or the Scarlet Witch towards Arkon (who later dated Storm, but his relationship with the X-Men was on friendlier terms). Arguably, this resulted less in creating interesting tension than just creating a less effective heroine.
 * The Mighty Thor 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 of Comic Books Green Lantern, 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 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 Star Sapphire personality made frequent appearances) as a long-time love interest.
 * Reversed in the case of Ray Palmer, the Silver Age Atom. His wife Jean Loring became the villain Eclipso after their marriage and divorce... and.
 * His successor as Atom, Ryan Choi was dating Giganta. It was apparently a serious enough relationship that.
 * 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.
 * Of course she DID conceive a replacement child in order to get out of the Six with no hesitation.
 * Captain Dynamo and Chrysalis from Dynamo 5
 * Daredevil has virtually made a career out of this trope. Elektra, Typhoid Mary... he never seems to learn.
 * While the Black Widow had long reformed when she got involved with Daredevil, her previous relationship with Hawkeye had an element of this for a time, between his Heel Face Turn and hers.
 * The Punisher also dated Elektra for a while - it ended badly.
 * Superboy (1990s clone version) dated New Goddess Knockout, under the impression she was a well-meaning thrillseeker, rather than a murderous sociopath.
 * Superman had a sexual relationship with New Goddess Amazing Grace. And Maxima. Oh, and he married the Kandorian Lyla (he had amnesia).
 * 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
 * When inept superheroine 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 Heel Face Turn a few chapters later.
 * In 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 Ireyon in Paperinik New Adventures - she comes onto our masked hero because she thinks he is 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 Really Seven Hundred Years Old.)
 * Greyshirt of Tomorrow Stories 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.
 * Given how close Kimber and Stormer are in Jem and the Holograms (far more so than the cartoon) they are, in effect, an LGBT example of the Trope.
 * Huntress and Catman had an on and off relationship ever since they fought for the first time. While it never got further than intense Foe Yay, 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. Recently Catman enacted a ridiculously complicated scheme to make Huntress give up on him because he wanted her to be happy with someone else. Catman had just been through a Trauma Conga Line that convinced him that he didn't deserve anyone's love, least of all Huntress'.
 * Zorro and Lady Rawhide in Topps Zorro series.
 * The Spirit has at least three - Silk Satin, Sand Saref, and P'Gell.
 * In Final Crisis, Snapper Carr hooks up with the Cheetah.

Fan Works

 * Detective Conan Boys Love Fanworks are full of this, since the most popular pairing is between the title character Conan Edogawa/Shinichi Kudo and his Phantom Thief rival Kaitou Kid. Alternately Kid can also be paired with his other biggest rival Saguru Hakuba or even Conan's best friend and fellow detective Heiji Hattori, 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 Death Note fanworks which has pairings such as Light (Kira, a Knight Templar Serial Killer Killer) 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 Serial Killer), Naomi and B (again, a detective and a Serial Killer), even Light and Misa (which has the dynamic I'll kill you if you are no longer useful / I'll kill you if you cheat on me) In fact Mello x Matt is the only popular ship in the Death Note 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 Dating Catwoman in fanworks with Kira and L: A Cure for Love, Constant Temptation, I Won't Say, Office Politics, The Prince of Death
 * All You Need Is Love ships Light and Naomi.
 * A very literal case is a major element in the 'verse of Cat Tales by Chris Dee, wherein a decision by Selina Kyle to open a one-woman Broadway show to present her side of the story ultimately results in her entering a serious and permanent relationship with Bruce "Batman" Wayne.

Film
"Amy: If you'll excuse me, I have a date with the devil."
 * The Incredibles: Mirage and Mr. Incredible (though the extent of their relationship is very unclear). Of course, the fact that Mirage  makes it more questionable.
 * Really only a partial example; they were never really in a relationship (Mr. Incredible already being married), 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 The Casanova 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 superhuman supremacist and thus not a nice person at all.
 * Out of Sight 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.
 * D.E.B.S.: both the short and full-length versions of this film center around a secret agent's forbidden Les Yay romance with a supervillainess.


 * The Thomas Crown Affair.
 * Most James Bond 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' plan to kill Bond, or the ladies became good when the Big Bad mistreated or betrayed them. From Russia with Love, Goldfinger, and Live and Let Die are the only ones where the henchwoman genuinely becomes a love interest.
 * Batman Returns, which makes Catwoman a good bit more sympathetic, if somewhat more insane (she's ).
 * 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 "I'm already seeing someone").
 * Batman XXX has Batman and Robin "dating" Catwoman.
 * Sherlock Holmes and Irene Adler definitely have an air of 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
 * This would have been the premise of the unmade Romance of The Pink Panther, which was ultimately scuppered after lead actor/co-writer Peter Sellers died: Inspector Clouseau falls in love with a woman who's actually the Classy Cat Burglar he's trying to capture.
 * The plot of Entrapment is based almost completely on this trope.
 * Warren Peace, an Anti-Hero type character in Sky High is a product of such a pairing.

Literature

 * In "Everlost" and its sequels, Nick and Miss Mary Hightower. One of the best played examples of this I've seen.
 * Vaintè and Kerrick in West of Eden.
 * Corran Horn and Mirax Terrick of X Wing Series. 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.
 * Luke and Mara in The Thrawn Trilogy and, of course, Hand of Thrawn. 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 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 Terry Pratchett and Neil Gaiman's Good Omens. They're Mistaken for Gay in the book, and Word of God 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 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, he found himself a witch.
 * John Taylor, from the 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.
 * Charles and Emma Darwin, in the book of that name.
 * In Real Life, though, they were friendly with each other.
 * Statonian Envoy Rhodney Antilles and RMM Agent Melanie Horquetza in Stationery Voyagers. It helps that Lord Abberwadd treats the Voyagers more as rebellious children than as actual enemies.
 * The Scarlet Pimpernel: Sir Percy and Marguerite Blakeney lived estranged for a year (during which the latter fell in love with his alter ego) before Marguerite's Heel Realization and redemption.
 * In Harry Harrison's The Stainless Steel Rat series, the first novel that introduces Angelina gets like this. At first, Jim only wishes to catch her for his 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 Shotgun Wedding), thus the following novels no longer fit this trope.
 * Tawnos and Ashnod from The Brothers' War (Magic the Gathering) are in love, despite being generals on the opposing sides in a war.
 * The only woman Hercule Poirot comes closest to being romantically involved with, is a highly skilled jewel thief.
 * In The Three Musketeers, d'Artagnan dates Milady for a while. And really, he is the one who lies to her.
 * Lymond Chronicles ... 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....
 * In Ayn Rand's "The Fountainhead" the hatred between critic Dominique Frankon 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.
 * In Rand's Atlas Shrugged 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 Jack Vance's 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 Sherlock Holmes work not by Arthur Conan Doyle, from professional novels to amateur fanfics, has this crop up between Holmes and Irene Adler, to varying degrees of intensity and success.

Live Action TV
"Prince: Do you still feel anything for me? Xev: A little. Prince: You shouldn't."
 * Dark Angel 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 Due South.
 * Captain Picard and archaeologist/thief Vash in Star Trek: The Next Generation.
 * Also Captain Sisko and Kasidy Yates in 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).
 * Xena and Ares?
 * With some squick, since it is strongly implied that he is her real father. (You know those Olympians.)
 * Jack and Nina from Twenty Four. Though all tension is gone from Jack's end and replaced with genuine hatred once
 * The Clark/Lana relationship on Smallville treads the line of this trope as Lana grows ever more ruthless and driven. Of course, this version of Clark is hardly the Big Blue Boy Scout, either.
 * And in the three episodes Alicia appears in, the Clark/Alicia relationship is this trope too.
 * 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.
 * Phoebe Halliwell and Cole Turner on Charmed, although initially he was just trying to seduce her so he could kill her, He eventually turned good...for a while...
 * Heroes...Mohinder and Eden, Sylar and Elle (at least at first), Matt and Daphne, Lydia and Samuel; it goes on forever, thanks to the show's Heel Face Revolving Door.
 * In NCIS Ziva had a relationship with a crooked, alcoholic Mossad agent. It failed, spectacularly.
 * In Stargate SG-1, 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 Reset Button.
 * In a 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 Sanctuary. They were engaged until Druitt . Now he alternates between helping and tormenting Magnus, but admits he still loves her. A recent episode implied she feels the same way.
 * Nate and Sophie's pre-series relationship on Leverage...even though he remained faithful to his wife and she believes he was never really tempted.
 * CJ and Danny from The West Wing 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.
 * Jack and Juliet from Lost. They started to develop feelings for each other before Juliet's Heel Face Turn. Then later, in the, 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 many Face Heel Turn and Heel Face Turn turns.
 * John Connor and Cameron in The Sarah Connor Chronicles. 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 Prince, Lexx.
 * Xev and Prince, Lexx.


 * Party Animals: 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
 * Servalan and Avon. The blatant flirting and occasional bouts of passionate kissing move this one out of the realms of 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 The Thick of It. 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 Battlestar Galactica, the relationship of is suitably star-crossed. And despite.
 * Buffy the Vampire Slayer: Buffy/Spike and, to a lesser extent, Buffy/Angel (the latter applies only when Angel actually does something evil, which doesn't happen a lot).
 * 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.
 * The mighty Les Yay subtext of Buffy/Faith.
 * Not just Buffy either. She 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. Faith 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 Heel Face Turn. And she teases Spike over what she or Buffy could do to him, then later they discuss sex and it's hinted they did it.
 * And there was one episode when Oz was into that other werewolf.
 * On Angel, Wesley and Lilah Morgan. Angel/Eve. (Lorne made them do it!) Angel/ Bad Girl of the Week Faith in season 3 and (arguably) Gwen Raiden.
 * For all the animosity between them, Firefly's Mal and Saffron do manage to show a teensy, tiny bit of affection toward one another - when they aren't Pistol-Whipping each other or leaving the other party naked to die in the middle of a desert. And don't forget, they technically are married.
 * Who hasn't she married?
 * Pops up in Dollhouse with the brief interaction between Bennett Halverson and Topher Brink. Both of them are hammered hard by their various Geeky Turn Ons 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, . 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 The Man from U.N.C.L.E., Napoleon Solo apparently has an ongoing flirtation with Angelique, an agent of THRUSH.
 * Gil Grissom and Lady Heather in CSI.
 * Omen of Dark Oracle, 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.
 * Power Rangers in Space: Zhane the Silver Ranger with Astronema. Yes, the main antagonist. The romance lasts just one episode, spoiled by another battle. Later on after the reveal, Andros the Red Ranger invokes  retroactively.
 * Power Rangers Time Force 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 Daddy's Little Villain and said Daddy Ransik is an Overprotective Dad; after Ransik puts Lucas through some Twerp Sweating he panics and starts going "Please Dump Me!" By the way, that poetry that Lucas wrote was actually for . They do seem to get together post-season, though, once Nadira and Ransik have both made Heel Face Turns.
 * In Power Rangers Ninja Storm Dustin with Marah, but she ends up betraying him after considering a Heel Face Turn. 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 Power Rangers Dino Thunder, with Tommy sharing an attraction with Principal Randall... who is really Elsa in disguise.
 * In Babylon 5, Vir Cotto helps Narns escape the Centauri occupation while his ditzy fiancee Lyndisty fondly remembers killing entire villages.
 * By series 6 of Doctor Who, the Doctor became romantically involved with a convicted murderer and psychopath raised to assassinate him.  but he keeps coming back for more.
 * Gary and Anna 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 Alias. Even though she was a KGB sleeper agent who posed as his wife and constantly walked through the Heel Face Revolving Door, 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...but what is not clear is whether it could ever have overcome her Rambaldi addiction.
 * Kono's mystery boyfriend on Hawaii Five-0 has turned out to be Adam Noshimura, the heir to Honolulu's Yakuza clan.
 * Kono's mystery boyfriend on Hawaii Five-0 has turned out to be Adam Noshimura, the heir to Honolulu's Yakuza clan.

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. 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.

Newspaper Comics

 * Krazy Kat and Ignatz Mouse refer to each other as enemies, but Krazy is madly in love with Ignatz and harbors the delusion that he returns these feelings. This is made more complicated by occasional hints that this might not really be a delusion.

Video Games

 * Sly Cooper and Carmelita Fox. He's a heroic Gentleman Thief, 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 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.
 * Turns out that your love interest in Quest for Glory IV game is
 * The situation with Silk Fox and the player (either gender) in Jade Empire starts out looking like this, before a variety of revelations related to the Gambit Pileup point out that she is most definitely a good guy.
 * Knuckles and Rouge from Sonic the Hedgehog fit this trope very nicely, especially in Sonic X.
 * Alex, the only real Love Interest in the Bastard of Kosigan series is also the brains behind one of the main villain's operation. Though, due to the story's Black and Grey Morality, 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 Harvest Moon - Magical Melody you can marry your rival, Jamie, who is always the opposite gender from you. Considering that in the original Japanese, there were 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 find all the magical notes.
 * Harvest Moon DS Cute also provided the option of marrying Gentleman Thief Skye.
 * MegaMan Volnutt and Tron Bonne in Mega Man Legends.
 * Leon Kennedy and Ada Wong of the Resident Evil series alternate between teaming up and pointing weapons at each other. All while oozing so much Unresolved Sexual Tension into the air that it could be cut with the proverbial knife.
 * in Tsukihime during her route. During the same route, there was a little with Akiha as well, but Shiki decided that their relationship didn't depend on blood. But for the main thing, it's the only way that actually gets to have a happy ending. In the rest, she either continues bottling up her emotions (canon personality)
 * In Assassin's Creed, the Assassin Altair and the Templar Maria end up falling in love, despite being enemies. This is shown in Assassin's Creed II, 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 switched allegiances in Assassin's Creed: Bloodlines, and canonically the romance came afterwards.
 * Otacon and Sniper Wolf in Metal Gear Solid.
 * The Warden and Morrigan in Dragon Age.
 * A Female Mage!Warden and ex-Templar Alistair.
 * Mage!Hawke and Fenris, or Templar-aligned Hawke and Anders or Merrill in Dragon Age II.
 * The Ship Tease between Templar!Carver and Merrill, as well as Circle!Bethany and Sebastian Vael.
 * Garen and Katarina in League of Legends, who quite literally got matched via a dating service, yet are champions of opposing countries.
 * Pokémon fandom is quite prone to this with the female player characters and the male antagonists, be they rival or villain. Especially in the fourth and fifth generations: Silver and N both get shipped with both player characters for their respective games, while Cyrus/Dawn is easily one of the most popular pairings for the Sinnoh games, despite the obvious issues.
 * Commander Shepard (Alliance) and Miranda Lawson (Cerberus) in Mass Effect 2.
 * World of Warcraft; the "Hot and Misty" novel in the Steamy Romance Novel series (drops you can find in-game) shows Marcus (an Alliance paladin) being intimate with a female blood elf (a member of the Horde). The "Big Brass Bombs" story suggests he also dates a female goblin (another Horde member) at least once. While "hero" and "villain" doesn't apply here, the Alliance and the Horde are enemies, and nothing in the stories suggests any characters are disloyal to their factions.

Web Comics
"Othar: What did I tell you about getting romantically involved with evil? Sanaa: "...It's not a bad way to kill time, as long as it ultimately results in the total destruction of her lair and the ruination of her nefarious plans!" Othar: Oh. Yes. Well, I meant—"
 * Evil Inc.: and . There was also an affair between  and  long ago, and lately  and  have developed a relationship.
 * Rip Haywire, with Rip and Cobra.
 * 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 even more.
 * Girl Genius: Baron Klaus Wulfenbach has canonical amorous history with Lucrezia Mongfish . 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.
 * A better example: The Baron's son Gilgamesh and main heroine Agatha Heterodyne, with the dramatic twist that though they're both noble and heroic… and Properly Paranoid. And circumstances keep putting them on the opposite side. And it was about four (real-life, not webcomic) years between their scenes together. Damn you, Foglios!
 * Othar Tryggvassen, GENTLEMAN ADVENTURER, has evidently done this at least once in the past, judging from an argument with his sister when he believed she'd developed a crush on Gilgamesh:


 * Umlaut House:, Eliza and Dr. Sisyphus.
 * In Casey and Andy, Jenn has been crushing on Quantum Cop for ages, and it recently 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. 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 Sluggy Freelance Torg has this situation when he develops a crush on Val, who is revealed to be.
 * And then there was his promise to marry Oasis...a promise he intended to keep. (One only wonders how will affect that...)
 * In 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 relationship was...complex.
 * Nor was it unwilling either...
 * In Everyday Heroes, Jane first sets eyes on Mr. Mighty when he's guarding a house that she's trying to rob. She tries to ambush him from behind; since he's invulnerable and she's not, this doesn't work well.
 * The Order of the Stick got Elan and Therkla, though it was unrequited on Therkla's part (Elan is completely devoted to Haley).
 * Roy and Miko were canonically attracted to each other at different points, and the author had originally intended them to be love interests, but quickly realized that it wasn't happening. Only a partial example, because the attraction was before they became enemies (and even when Miko was an antagonist, she wasn't actually evil).
 * Deconstructed with Durkon and Hilgya. They were attracted to each other, and seemed to be coasting towards a Relationship Upgrade, 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 Tear Jerker
 * In The Adventures of Dr. McNinja, 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.  Later, she's revealed to be working with , but there's still some romantic tension between the two.
 * Super Stupor demonstrates this one played pretty straight...except that it's the morning after.
 * Bob the Angry Flower 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.
 * Lightbringer, a web comic by Linkara, gives us the issue Masks, where Lightbringer's girlfriend Sandy is revealed to be the the Scarlet Baroness, who's Hannibal Lecture on Secret Identity Identity actually throws Lightbringer off guard forcing his sidekick into pulling a Get a Hold of Yourself, Man!. Also it's the issue where Chad Rocco, fellow That Guy With The Glasses contributor joins in.
 * In Dubious Company, Mary thinks she is this with Elly. Elly highly disagrees.
 * Fan speculation suggests this might end up being the situation for Questionable Content Marigold and Dale, who play on opposing sides in World of Warcraft.
 * What's New with Phil and Dixie once explored this in Magic the Gathering-based soap opera comic.
 * In Jet Dream, Harmony Thunder (back when she was Jack Thunder) had this type of relationship with the mercenary Raven Red. Harmony's sex change puts further strain on the relationship.
 * Dangerously Chloe has Pandora (another young succubus from Tarterus Academy and Chloe's best friend there) dating an angel. It's not like she's quite head-over-heels about "Zachy-poo", but they get along well. Pandora's main reasons for looking at the traditional enemies this were being good looks and being invulnerable enough to stay alive after bedding a succubus inexperienced enough to lose control (he did look like dragged through thorny shrubbery for a hour, but a human would be torn apart, and most demons are too cautious to approach the succubi as infamous for going wild violently). Generally, the angels make perfect butts for her jokes and she repeatedly managed to sneak into Heaven in disguises that don't look awfully convincing to prank them. Which tend to cause confusion, and if the locals figure out what happened, they try bringing the nefarious perpetrator to justice, which requires sending a team including one Zachuriel to catch her in the "overworld"… where she can meet him alone after the rest scatter and get distracted by watching so many mortals doing strange and shocking human things.

Web Original

 * One of Shadow of the Templar's main plots is the developing relationship between FBI agent Simon Drake and Gentleman Thief Jeremy Archer.
 * The Rocket of Legion of Nothing 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 PBEM Universe is having a torrid affair with Brigit, the daughter of Lord Doom via one of his copy bodies.
 * In Chaos Fighters II-Cyberion Strike, go as far as an actual date after  a subversion occurs when she pulls a Heel Face Turn later on.
 * According to their actors, The Nostalgia Chick and The Nostalgia Critic. Neither of them are heroes or villains in the traditional sense, but their Foe Yay and Not So Different-ness are off the charts.
 * In The Guild, Codex finds herself getting intimately involved with the leader of her guild's villainous rivals.
 * Eric had sex with Sister in Mall Fight 3, and remains on good terms with her. As much as one can be with Sister.

Western Animation
"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?"
 * In an episode of Batman Beyond, 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. "Let tell me you about a woman named Selina Kyle..."
 * Eventually the girl leaves her family's gang and even manages to get a regular job and lifestyle, unfortunately Terry is with someone else by then. 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.
 * In one episode Bruce is shown disconsolately flicking through pictures of ALL his hot female adversaries - Catwoman, Poison Ivy, Harley Quinn, and others - and the scene suggests he at some point in his career has been attracted to all of them.
 * Danny and Valerie on Danny Phantom. Although in this case, only he realized it; Valerie didn't find out Danny's secret identity until the Grand Finale, long after their relationship ended (ironically, for It's Not You, It's My Enemies reasons).
 * Parodied on The Simpsons, when Bart has a Radioactive Man comic book in which the hero marries "Larva Girl". The issue's title is "To betroth a foe!"
 * Until she eventually converted to his side, Blackarachnia and Silverbolt had this kind of relationship in Transformers: Beast Wars. True, she was originally a Maximal converted to the enemy's side via Brainwashing, but still...


 * To bring Blackarachnia into Transformers Animated, she became Optimus Prime's Catwoman. Or, at least she will be when she gets over getting left behind.
 * Jake and Rose on American Dragon: Jake Long. Before Rose learned of Jake's Secret Identity, she was also his Lois Lane and his Girl Next Door.
 * Aeon Flux and Trevor Goodchild, of course. Though which of these is the villain is debatable.
 * In 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 lead to a considerable ammount of character development for him later. Didn't make much sense since he'd previously tried to kill her, but many found it sweet.
 * Keeping on the X-Men theme, Wolverine and the X-Men does this with Nightcrawler and the Scarlet Witch. 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,  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.
 * Dave and Princess Irmaplotz in Dave the Barbarian.
 * The Venture Brothers 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.
 * Spy Groove. Spy #1 finds himself falling for Sierra Nevada, who's brilliant, gorgeous and evil.
 * The old Sunbow G.I. Joe 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 COPS, COP Sgt. Mace and cat-burglar Nightshade had a romantic relationship despite being on opposite sides of the law.
 * Teen Titans: 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 Heel Face Turn.
 * El Tigre featured the titular character and 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, Frida Suárez, is rivals (and not of the friendly kind) with Black Cuervo's civilian persona Zoe Aves... with whom Manny seems to get along fine. Cue Love Triangle.
 * 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. Generation Xerox played straight.
 * Justice League: 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 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 Heel Face Turn 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.
 * Darkwing Duck had the titular 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 pretty quickly went straight after falling for Darkwing, too. She even knew his secret identity by season three.
 * On Word Girl, kid villain 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 The Grim Adventures of Billy & Mandy, paranormal exterminator Hoss Delgado winds up dating Eris, goddess of chaos.
 * Rex and Circe from Generator Rex. And 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.
 * Batman the Brave And The Bold 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,.
 * 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 Death Trap, and when he asks why, she kisses him. He takes it stoically. "I see."
 * One episode also has Jonah Hex hooking up with Lashina, depicted here as a henchwoman of Mongul and Mongal.
 * In Superman the Animated Series brainwashed Superman and Lashina of the Female Furies.
 * On 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 Krypto the Superdog, the whole Batman/Catwoman thing even extends to their respective pets, Ace the Bathound and Isis the cat.
 * Young Justice has Red Arrow marrying the Dragon Lady assassin Cheshire after his fall from grace. The two quickly split up due to Cheshire's refusal to give up her life of crime, but not before
 * The Spectacular Spider Man has the usual heavy flirting (and one kiss) between Spider-Man and Black Cat. However, they part on less friendly terms after.
 * Discussed in the Kim Possible episode "Animal Attraction"; Senior Senior Sr. advises his son against wooing Kim, claiming, "dating an arch-foe is spitting upon villain tradition."
 * Superman hit on Harley once in her own series, but it never went further than that.

Truth in Television

 * Surprisingly, this has in fact happened. Of course, neither person was evil, unless you think political pundits and strategists are evil (an entirely valid position), in which case both are. American political strategists Mary Matalin (a Republican, and quite conservative) and James Carville (a Democrat, and liberal enough) faced each other across several elections in The Eighties, culminating in the 1992 campaign (in which Carville engineered Bill Clinton's winning strategy), still regularly appear across from one another on political debate shows, and call one another 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.
 * Australian politics (as of March 2012): there are those who ship Julia Gillard (Labor Prime Minister) with Tony Abbott (Coalition Leader of the Opposition). There is even RPF for it. Not likely to eventuate, as Abbott is happily married (and takes his vows very seriously) and Gillard is unmarried but partnered, but if it ever did it would be a clear case of Heroes Want Redheads.
 * Julius Caesar and Cleopatra VII's famous affair, which took place while Rome and Egypt were geopolitical rivals.