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Dating Catwoman

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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..."

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

As the name indicates, this tends to be the gender dynamic of a male hero and a female villain. A female hero and a male villain is far rarer, but not unheard of (speculation as to why this gender dynamic occurs can be found on the Analysis page).

Their different senses of morality will conveniently keep things from progressing too quickly and sometimes they won't move at all, since the character won't 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.


A Sub-Trope of Opposites Attract. Compare Go-Karting with Bowser (when the relationship is platonic rather than romantic or sexual), Loves My Alter Ego (for similar relationships between heroes and bystanders), and Defecting for Love (which happens when the Catwoman decides to go straight after all). Easily overlaps with Villainesses Want Heroes, Trickster Girlfriend, and All Girls Want Bad Boys. 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 Romance Subtext for the less explicit version of this, and Fatal Attraction when it's more dangerous. See also Likes Clark Kent, Hates Superman or related tropes, when they have different relationships inside and outside of a Secret Identity. Compare Friendly Enemies.


Has nothing to do with dating a Cat Girl. Usually.


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     Anime & Manga 
  • Akame ga Kill!: Esdeath is truly and completely in love with Tatsumi. Esdeath 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. While Esdeath is unaware of this fact, Tatsumi tried a Love Redeems on Esdeath more than once, trying to use her love for him to make her become good, but gave up quickly when he realized Esdeath is completely insane and can't change.
  • The central romance in Cat's Eye is between Hitomi and Toshio. Although Toshio remaining unaware of it is a crucial part of their relationship.
  • 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.
  • 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 traveler (who is actually Bulma and Vegeta's future son) 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 Android #18. After a time skip of seven years, it's shown that they got married and had a kid (since she's technically a cyborg, not an 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.
  • One of the oldest anime examples is Go Shogun, where the closest to an Implied Love Interest for the Action Girl Remy Shimada is none other than the villainous Leonardo Medici Bundle.
  • Gundam:
  • Kaitou Saint Tail and Asuka Jr.; in this case, the lead, a Phantom Thief that steals back stolen items, is the Catwoman-ish one.
  • 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.
    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, 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.
  • Lupin III: One of the oldest and longest running examples is the on-again/off-again love affair between Lupin and Fujiko. They've been at odds with each other as often as they've met over candlelit dinners and, occasionally, the bedroom. She knows he's liar and a cheat, he knows she can't be trusted... and neither would have it any other way.
  • The whole premise of Maoyu. The Hero and the Demon Overlord both say Screw Destiny to their respective roles, hook up and try to find a way to end the war without gutting their respective war economies.
  • One Piece: During an SBS segment it's heavily implied that Viola had a sexual relationship with Doflamingo (the same man who had her sister murdered, overthrew her father, and forced her to work as an assassin in exchange for said father's life).
  • Ruby and Courtney from Pokémon Adventures 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 her realize all that his father sacrificed for his sake).
  • Since Phantom Thief Jeanne is heavily inspired by Kaitou Saint Tail, Jeanne also has a romance with her main rival, Chiaki aka Sinbad. Justified in the manga: It turns out that the two are, in fact, Adam and Eve.
  • Precarious Woman Executive Miss Black General has its main premise revolve around how the titular Black General is deliberately trying to invoke this with the hero Braveman, as she's utterly obsessed with him while also believing the best way to get romantically close to a hero is to become a villain and antagonize him, expecting their constant clashing to eventually cause him to fall for her. Unfortunately for her she's Wrong Genre Savvy, since the Affectionate Parody nature of the story instead results in her being an Abhorrent Admirer that Braveman greatly prefers to defeat and get away from as quickly as possible.
  • 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. Keith Green also falls for Katsumi, although again it's one-sided (she has no idea).
  • Happens in Red Garden when Kate ends up dating 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.
  • Sometimes happens to Minako Aino from Sailor Moon:
  • Shadow Lady has Aimi Komori aka the titular Shadow Lady (a waitress that can transform into the titular Classy Cat-Burglar) and Bright (the local Sympathetic Inspector Antagonist).
  • Deconstructed in Space Patrol Luluco. Luluco's dad is a member of the Space Police. Her mom is a Space Pirate. While the two are legitimately in love, their marriage was extremely volatile, ended in divorce, and left their child a bit messed up.
  • In Special Duty Combat Unit Shinesman, Matsumoto, a young businessman who is secretly a superhero protecting the Earth, accidentally sees the 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 definitely embraces the 'kill him' option until the very end of the manga, when he tells Matsumoto he's changed his mind.
  • In Super Dimension Fortress Macross/Robotech, the Zentraedi ace pilot Miria Fallyna/Miriya Parino falls in love with Terran ace pilot Max Jenius/Max Sterling, after literally engaging him in several duels and stalking him with intent to murder. They end up marrying and, in the Macross continuity, go on to have multiple children before becoming the two main leaders of the Macross 7 fleet.
    • In Robotech, they 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).
  • 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.
  • 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.
    • There also is a one-sided romance between Quiche and Ichigo, with the former being madly in love with the latter. His love gets creepier as the show goes on... until the end when Quiche refuses to kill Ichigo and gets killed himself. Ichigo is genuinely upset by his death. He gets better, though.
  • In UFO Robo Grendizer — one of the Mazinger Z sequels — Duke was engaged to Rubina, daughter of Big Bad. They loved each other. However he did not think they could be together again after what the Vegans had done to his homeworld.
  • 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 everything ends up ending well for them.

     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 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. But all that Character Development in their relationship has been 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 stop her from having costumed sex with him though. And then in DC Rebirth not only does he reveal his identity to her again, he proposes. It remains to be seen how this plays out, though.
    • 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 with 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. 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 Crisis of Conscience, the follow-up to Identity Crisis, Batman expresses fear that Catwoman’s Heel–Face Turn (or at least, Heel-Anti-Hero turn) was due to Zatanna manipulating her mind.
    • 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. 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.
    • Zigzagged with Harley Quinn; she doesn't show any affection to Batman other than occasional flirtingnote , but she was briefly intimate with Bruce Wayne in one New 52 story.
    • Depending on the Writer, Poison Ivy may have a downplayed, one-sided version of this; she is sometimes portrayed as attracted to Batman, viewing him as either a worthy rival, the only "good" man she knows, or both, but Batman does not reciprocate the attraction.
    • In an issue of The Brave and the Bold 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.
    • In Batman Beyond, Terry tries to invoke this trope upon meeting a new Catwoman. She refuses. This trope is later played straight, when she ends up sleeping with Dick Grayson.
    • Inverted in Catwoman: Guardian of Gotham. Selina dates and marries Bruce thinking that he's a handsome, good-hearted man, and feels nothing but utter revulsion towards the psychotic Batman. Too bad they happen to be the same person.
  • Superman:
    • For a long time, Lois Lane was both Superman's primary love interest and one of his main antagonists. She was constantly trying to expose the fact that he was really Clark Kent, which would of course have wrecked his life. He had to work very hard to keep one step ahead of her, even as he was also drawn to her.
    • In the New 52 Batman/Superman book, after Kal-El loses his memories of ever meeting Batman and those of the Kent's lessons he and Selina begin a relationship before he (Superman) gains back those specific memories.
  • Other examples from The DCU:
    • Captain Atom wound up marrying Plastique, a former Quebecois terrorist with explosive powers. Appropriately, in Justice League Unlimited she died in his arms, or at least she appeared to; she was never seen again but it was never confirmed if she truly died or not, while her comics counterpart is still alive and well.
    • The Golden Age 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 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 she took vengeance on his murderer.
    • 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 decided to use Lian's existence to torment Roy as payback for leaving her. Roy gained permanent custody of Lian after Cheshire destroyed the country of Qurac for shits and giggles. While the two aren't together anymore and Roy knows how awful Cheshire is, there still seem to be lingering feelings between the two that Roy is having trouble processing, mainly because of how it all effects Lian. This constantly causes drama whenever Cheshire reappears in Roy's and Lian's lives. However, it's implied Cheshire is such a sociopath she's incapable of having real love for Roy and mainly exploits Roy's feelings to use him and screw with him. This is a woman who conceived a replacement baby when her daughter's well being was used as a bargaining chip against her. It's also implied if Roy knew just how little Cheshire cared about Lian he'd want nothing to do with her, if not outright try to murder her for such disregard of Lian's life.
    • Superboy (1990s clone version) dated New Goddess Knockout, under the impression she was a well-meaning thrillseeker, rather than a murderous sociopath.
    • In Final Crisis, Snapper Carr hooks up with the Cheetah.
    • Supergirl (not the original, a shape-changing alien called Matrix) had a sexual relationship with Lex Luthor (who had put his mind into a cloned body of his younger self). She didn't know since Lex was posing as his own estranged son at the time.
    • Prior to the 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.
    • It is revealed in Watchmen that Night Owl II had a fling with Twilight Lady. It's not clear how far this went, though Dan keeps a framed picture years after retiring and seems deeply embarrassed when pressed for details. Before Watchmen: Night Owl reveals that the two did have a very, VERY sexual relationship, however brief and ultimately doomed.
    • This trope’s prevalence in the DCU is darkly deconstructed in James Robinson’s Starman run; the Mist, Starman’s Archenemy, is an obsessive Yandere who’s so convinced that Starman secretly loves her that eventually she rapes him. Double Standard: Rape, Female on Male is completely averted.
  • Marvel Universe:
    • 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.
    • Spider-Man and the Black Cat who become Spider-Man's girlfriend for a couple of years before he married Mary Jane Watson and on-and-off lover after the "divorce". And things between them soured badly during the Superior Spider-Man's run-in with the Cat (who, like everyone, didn't know that Doctor Octopus had taken over Spidey's body): he beat her up and left her to the police without so much as a "hello". Not only was she arrested, but everything she's pilfered over the years was confiscated. This caused her to snap and perform a full-on Face–Heel Turn. Her "queenpin" lifestyle led to nothing but stints in hospital and general humiliation from more experienced mobsters, and she eventually turned good again. She realized the reason she couldn't think straight was because she no longer knew Spider-Man's identity. Peter ultimately decided to share his secret with her, triggering a much needed reconciliation.
    • 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 Reigning" storyline saw the two wed, and have a son named Magni. But these events were eventually wiped from reality.
    • 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.
    • Daredevil has many. Elektra, Typhoid Mary, etc. 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 Fantastic Four's Human Torch briefly dated a villainess from the future known as Psionics. Johnny Storm also dated (and eventually married) a Skrull named Lyja who impersonated Alicia Masters (Ben Grimm's longtime girlfriend). Arguably, as this was all part of a plot and the Torch didn't know who she really was, this may not count. But the two later revealed that they had indeed developed strong feelings for each other.
    • Storm of the X-Men is a notable case in that it's practically become a running gag (and yes, it's been lampshaded) that villains want her (and sometimes Storm herself is interested back). No less than Doom himself decided at one point that Storm would make for a perfect consort.
    • Ant-Man ended up having this kind of relationship with Beetle. He didn't take this development well because when he first became a superhero Captain America expressly warned him to avoid this trope.
      Ant Man: (while lying in bed naked with Beetle) I'm so sorry, Captain America.
    • Karolina Dean of the Runaways first encountered her sometime 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.
      • In Rainbow Rowell's Runaways, Gert and Victor become a couple, despite both of them knowing full well that in at least one alternate timeline, they were mortal enemies.
    • In a miniseries from the 90s, Greer Grant-Nelson aka Tigra of The Avengers infiltrated a police academy to find answers about the murder of her husband Billy. While there she met and fell in love with Sergeant Matt McMullin who was an instructor at the academy. Unfortunately for Greer, Matt was involved with the Brethren of the Blue Fist, a group of vigilante cops operating out of the academy. Worse, Matt was revealed to have been the one who killed Billy to keep him from exposing the Brethren's crimes.
    • All-New Ultimates: Miles Morales received a "Take That!" Kiss from Diamondback. It was not mutual nor consensual, but got worried that he may not be loyal to Kate Bishop because of it.
  • Dynamo5 : Deconstruction. Captain Dynamo had an affair with one of his enemies, a supervillain named Chrysalis, and had a daughter with her, who he help raise. While Chrysalis herself said that they were in love, that did not stop her and her daughter from taking advantage of his death to impersonate him to increase their power base. Ultimately, Chrysalis, a amoral and ruthless criminal who is willing to murder anyone in her way, who only escapes justice because of her affair with Captain Dynamo.
  • Disney Ducks Comic Universe:
    • Subverted with the Ireyon in the Danish Paperinik stories - she comes on to our masked hero because she thinks he is Fantomius, her old flame, whose style and equipment is the base of the one 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 700 Years Old.)
    • Played straight instead with Lola Duck, another female thief who often uses her beauty to take advantage during her work. Paperinik is not immune to her charm. Indeed, he just stops her attempted theft, but never arrest her. Despite they share a strong attraction, their relationship end because of the respective roles.
    • Played with by Colonel Neopard and Commander Alyonesse: as mercenaries they're competitors, but at the end of the day they'll date without an issue (Neopard even named his ship after her real name). Also, it's not clear who's the Catwoman, as they're both mercenaries, and while Neopard found himself fighting on Paperinik's side in both of his appearance that was just by coincidence the first time (Neopard's targets had a base on Earth and were allied with Paperinik's enemies the Evronians) and outright trickery the second (he was losing and needed reinforcements, and tricked Paperinik into coming to his rescue hoping he'd bring some powerful war machine), and in he's been known to fight for people who'd rather fight a war rather than pay for something they bought (his client before the job that brought him to Earth didn't pay their bills to a merchant coalition-or the mercenaries they used to defend themselves, hence why Neopard ditched them-, and in his second appearance he's working for a minerary company that wants to keep the industrial planetoid Grullop because the builders went over budget), while Alyonesse, in spite of being the enemy when she appeared, was fighting for Grullop's builders to recover the planet after the buyers refused to pay.
  • 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.
  • Played with regarding the titular Fox from The Fox Hunt and Dream Demon. They used to date each other back when they were both innocent kids, but have only just met again recently, well into their adult lives, with The Fox being married with children by this point, the youngest being in his teens.
  • The Fixer and Natalie Stack in Holy Terror.
  • In Jem and the Holograms Kimber is dating the Token Good Teammate of The Misfits, Stormer. Stormer isn't bad or anything, but her band is constantly butting heads with Kimber's band.
  • 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.
  • In ReBoot it's suggested that Mouse and Bob had this relationship before he arrived in Mainframe. He arresting her when she tried to hack into the Supercomputer and Mouse flirts with him constantly.
    • The virus Hexadecimal also has a "thing" for Bob. He is polite with her, even going to far as to be a Friendly Enemy, but he still has to stop her from causing chaos through Mainframe.
  • In Sherwood, Texas, outlaw biker Rob Hood is romantically involved with Maria, the daughter of the Sheriff of Nottingham County.
  • The Spirit has at least three - Silk Satin, Sand Saref, and P'Gell.
  • 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.
  • In W.I.T.C.H., Orube fell in love with Cedric, and they dated until his Redemption Equals Death.
  • Witchblade bearer and cop Sara Pezzini and The Darkness bearer and Mafioso Jackie Estacado are rivals in their professional and supernatural lives, but as of First Born they have a daughter, Hope, together.
  • Zorro and Lady Rawhide in Topps Zorro series.

    Fan Works 
  • Lampshaded in Amazing Fantasy. After Izuku talks to a girl for the first time, Peter advises him not to date anyone on the other side of the law, not even morally ambiguous cat burglars. He's also turned off by Toga's Blood Lust for him.
    Peter: Here's a bit of free advice before you hit the dating scene. [jabs a finger at Izuku] Do. Not. Date. Supervillains. Not even morally ambiguous cat burglars.
    Izuku: I-I wouldn't!
    Peter: Yeah, that's what I said too. But every member of the opposite sex that's on the other side of the law seems to enjoy wearing as little as possible or too much leather, and… [shakes his head] Ah, forget it. Just keep that in mind before you head to school.
  • Batman Beyond Revisited: Jake’s relationship with Inque became this for a short while, before she joined the team.
  • Cat Tales: Almost the entire reason for the existence of this now almost 20 year old series (still going). Starts with Catwoman protesting her portrayal in the local tabloid the Gotham Post in an off-Broadway show. Which Prompts Batman to negotiate a Relationship Upgrade. Selina is living in Wane manor by volume 3.
  • In the Doctor Who fanfic The Courtship and Marriage Rituals of Time Lords, the author created an alternate universe scenario where all of the Master's schemes weren't actually schemes, but dates, and Last of the Time Lords was his marriage proposal. And no one bothered to tell the humans.
  • In Deserted Distractions, Yami Bakura and Tea begin to have this relationship, to both parties' disgust and arousal.
  • Detective Conan Yaoi Genre 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.
  • Entrancing Wendy is a Peter Pan fic where a married Wendy finds herself falling for Captain Hook after she reunites with him in England.
  • Lilgrimmapple's Gone Batty II: Eclipsed is setting Melody and Goth up for this after their Foe Romance Subtext in the first story.
  • Infinity Verse: It's revealed in Chapter 6, the Manny Rivera/El Tigre has resumed dating his former rival Zoe Aves/Black Cuervo.
  • In The Institute Saga, Superman ends up dating Mystique.
  • Le Papillon Rising: Adrien and Marinette are adorably in love with each other, while Papillon works to steal Ladybug's earrings. After the breakup, Ladybug and Papillon themselves put aside the battle to make out on a rooftop, while pretending the other person is the one the just broke up with, ending in moaning each other's civilian names and somehow still not putting the pieces together. Um.
  • Less Than Zero has Supergirl and Null, the alien being intrigued by the surprisingly affable thief. There's a bit of friction between them as Null is unrepentant about being a criminal, but it works as he's not really destructive. Oh, and he also was mentored by Catwoman, she of the Trope Namer.
  • The Many Dates of Danny Fenton (Danny Phantom Western Animation, TV Series, and Comic Books.): Danny unknowingly goes on a date with the Black Cat, who flirts with him in and out of costume.
  • In Mega Man Recut, 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.
  • In My Pain, My Thrill, Princess Peach is in a Secret Relationship with her political enemy King Bowser. The two even have a son together, Bowser Jr.
  • Deconstructed in one day at a time with the Trope Namer. As explained by Jason Todd to his adoptive daughter Helena Wayne, her parents did love each other, but were plagued with doubts about their relationship because they didn't know where'd they stand without being Batman and Catwoman, and the dynamic that entailed. It led to a cycle of self-sabotage that left them both unhappy in the end. He repeats this explanation to Bruce, and straight out tells him that if he still wants a relationship with Selina, they need to figure out where they stand as Bruce Wayne and Selina Kyle first.
  • Eventually happens between Harry and Voldemort/Tom in A Snake Named Voldemort, but only after Voldemort pulls a bit of a Heel–Face Turn.
  • Son of the Sannin has Ino and Sai during the Root Arc. While the two of them are a couple (just don't say that within earshot of Ino), both of them are under orders to spy on the other and are fully aware of the other's intention.
  • A literal example in A Spark of Genius were Xander Harris end up in a relationship with Selina Kyle, a relationship she finds more enjoyable and straight forward than her one with Batman, since Xander isn't bothered about he criminal activities and has a sense of humour.
  • Spider-Man Symbiotic: This ultimate Spider-man spin-off has a symbiote infused Peter having a long-term temporary fling with Black Cat a Marvel Comics Expy of Catwoman because she reminds him of White Tiger, whom is in a relationship with Luke Cage though it's a bit rocky with their beliefs of Peter being dead and all.
  • In The Techno Queen, Armsmaster and "Evil" Dragon. Clockblocker and TTQ. Flechette and Parian/Velvet Villain.
  • Deconstructed in The Touch of Green Fire and its sequels. Kim falls for Shego and the two begin having an intimate relationship, but Shego cuts it off a few weeks later by pretending that it was a meaningless fling. The maturity differences due to their age gap is trouble enough, but the fact Kim is a hero and Shego is a criminal means that their relationship could lead to more problems.
  • In Unstable Equilibrium, Korra is the Avatar and she's unknowingly dating an Equalist, her girlfriend Asami.
  • In Voldemort Goes Back To School, 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 "heated stares" and comes to the conclusion that he has a crush on him. Hilarity Ensues.
    Voldemort: This was not how wizards dueled!
  • The Vow: While Lord Shen's Face–Heel Turn drives a wedge between him and his fiancée Lady Lianne for three decades, neither can let go of their love for each other. As Lianne struggles both to stop Shen's evil plans and reach out to him, Shen intends to make Lianne his queen both as retribution (until he forgives her) and out of love. When Shen releases Lianne in the midst of their wedding to free her from his dark road, she gives her marriage vows before leaving. Eventually Shen is forced to settle to living anonymously with Lianne and their son.
  • Double Subversion in With This Ring. Renegade!OL invoked the trope to cover up that Cheshire was his informant and mole for the League of Shadows. He later admits that he does desire her romantically after he keeps seeing her despite her no longer being useful as a spy. Cheshire and Renegade!OL become engaged.
    • Both played straight (metaphorically) and averted (literally) with Batman, who is currently in a relationship with Talia al Guhl, daughter of Ra's. Both Selina Kyle (Catwoman) and OL think that Catwoman would be better for him.
  • There's even a good amount of Crash Bandicoot fanfiction where the titular hero gets paired with Nina Cortex, of all girls.
  • Fanfiction about Danny Phantom will usually pair the title character with fan favorite villain Ember McLain. The two don't show any interest in each other in canon, only being a Fan-Preferred Couple.
  • Death Note fanworks:
  • 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.
  • An overwhelming number of Good Omens fanfics ship the angel Aziraphale with the demon Crowley, many of them touching on how deep in trouble they could get in if their superiors in Heaven and Hell ever found out about their relationship and/or how their fear of exactly that makes them reluctant to admit/act on their feelings for each other for a long time.
  • A good fifty percent of all Kim Possible fics seem to be focused on KiGo... that is Kimmie and Shego becoming an item... and as likely as not having kids and getting married... sometimes in that order. However, many KiGo fics veer away from this trope by having one of them permanently switch sides, either by Shego going legit or Kim being seduced into criminality.
  • 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.
  • The Bridge has two villains fall into this on opposing sides. Monster X and the Sirens are forced into an Enemy Mine for an arc against a common foe, and overtime X and Aria Blaze develop honest feelings for one another. It was strong enough to give both a power boost based on love magic by the end. This is despite X having originally been sent by his master to acquire the Siren's powers. It helps that while they are members of villainous factions, neither is especially evil or amoral: Aria wants to protect her family, while X was willing to use non-lethal means of taking the Sirens' gems. Eventually X and Aria not only bury the hatchet, but become full on lovers, and X and his crew become allies of the Sirens.
  • A Rabbit Among Wolves: In this story, Jaune ends up in charge of the Vale branch of the White Fang. Coco flirts with him and genuinely enjoys his company. Justified in that Jaune is only a terrorist in the loosest definition of the word, has slowly turned the White Fang into more of a freedom-fighting organization, and isn't at all antagonistic to Beacon. Coco herself is genuinely moved by his good deeds and impressed with his uncanny ability to manipulate public opinion in his favor.

    Films — Animated 

    Films — Live-Action 
  • Fritz Lang:
  • Out of Sight involved a romance between gentleman bank-robber Jack Foley, and US Marshal 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.
    Amy: If you'll excuse me, I have a date with the devil.
  • 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.
  • In The Sting, the grifter Johnny Hooker (Robert Redford) plays a very dangerous cat and mouse game with the Mafia. They want to kill him and for that purpose hire various hired killers, he plans a "big con" to cheat their boss of a lot of money. In one scene, a hit man nearly catches Hooker in a restaurant. A waitress named Loretta (Dimitra Arliss) saves his life and he ends up spending the night with her. However, on the following morning it turns out that she was herself a hired killer, the feared Loretta Salino, and that she intended to kill Hooker herself - his life being saved at the last moment by a hit man on the side of the Good Guys who kills her in the nick of time. What is understood of her motivation is that she saved Hooker from the rival killer in order to claim the reward herself, and she killed the rival in punishment for intruding on her turf; that she regarded killing Hooker as a professional obligation, with no personal animosity involved; and that the plan to kill Hooker in no way precluded enjoying sex with him first.
  • The Dark Knight Rises 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 and they ultimately end up creating new identities and leaving Gotham together.
  • Batman Returns, which makes Catwoman a good bit more sympathetic, if somewhat more insane (she's more in the crime business to get revenge on her murdering boss and knows she can't live with herself when it's over). You can see at the quotes section that when Selina and Bruce are dancing and they realize her other identities, they are very afraid.
  • Batman & Robin: Robin believes he is doing this with Poison Ivy. He falls in love with her and believes she loves him too, and even after finding out she is a villain he believes that she loves him enough to change sides so they can be together. Averted however, as Ivy is only pretending to love Robin to drive him and Batman apart and kill them with her Kiss of Death. The two do “break up” though. Robin wises up and protects himself from the effects of Ivy’s kiss, and Ivy, angered that Robin tricked her into revealing her plan and stole a kiss from her, shoves him into her pond to drown him, officially ending whatever “relationship” they had.
  • Catwoman (2004) 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 told "I'm already seeing someone").
  • Sherlock Holmes and Irene Adler in Sherlock Holmes (2009) 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 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 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.
  • In Sky High (2005), Warren Peace, an Anti-Hero type character and protagonist Will's rival, is a product of such a pairing. Warren is the son of a superheroine and a villain, the latter put in jail by Will's father.
  • Lifeforce. The astronaut protagonist is obsessed with the beautiful space vampire he is hunting, even though to touch her means death. They nevertheless make out several times. There's even a Ho Yay moment when he's driven to kiss her while she's 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.
  • Played straight in Indiana Jones and the Last Crusade. Indiana and Elsa Schneider first meet in Venice and begin a sexual relationship as they look for clues to the Holy Grail’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.
  • It happens to an extent in Revenge of the Sith, as Anakin and Padme, secretly married at this point, are at odds over Chancellor Palpatine and the new direction of the Republic. Anakin sides with Chancellor Palpatine while Padme leads the political opposition against him. Hints of this were shown earlier in Attack of the Clones, when he talks about how much he hates politicians and that a system with a benevolent dictator would be superior.
  • In Joyeux Noël, the German lieutenant reveals that his excellent French is due to his French wife while their countries are at war.
  • The Penalty: Rose the police agent falls in love with Blizzard the criminal mastermind, despite how evil he is. Meanwhile, Blizzard develops feelings for Rose that stop him from killing her even after he finds out that she is an agent for the police and she is conducting The Infiltration of his organization.
  • In Petticoat Planet, the mayor and the sheriff of Puckerbush are bitter rivals who are at constant odds over the best way to run the town. They are also in a lesbian relationship.
  • Advance to the Rear: Captain Heath and confederate spy Martha have some flirtation despite remaining firm in their respect, conflicting, loyalties and both being aware of it.

  • Played straight in the Alterien series; despite the fact Helena is a ruthless and morally ambiguous business woman with criminal connections, Oberon eventually falls for her charms.
  • Alcatraz Series: Attica is the heir of the Smedry clan, a family of once-royalty with magical talents who lead the fight again the evil Librarians who now rule more than half of the world. Attica falls in love with and ends up marrying a Librarian named Shasta. They're a rather more deconstructed version than usual, and by the time of the books, they've been separated for almost 13 years—although they're not actually divorced. It's clear why they don't work as a couple, but it's also clear that they still have some love for each other. When they finally do share a scene together, there's the kind of banter you'd expect from this trope.
  • In Everlost and its sequels, Nick and Miss Mary Hightower.
  • X-Wing Series:
    • Corran Horn and Mirax Terrik in the Rogue Squadron books. 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, 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 Becoming the Mask and falling in love with him. She's forced to fake her death, but Mercy Kill reveals they eventually found each other and are Happily Married with children.
  • 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 (whose final assignment was to assassinate Luke). 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.
  • 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.
  • There is a short sci-fi story about a female investment banker in the future, whose job is to spend the day looking for emerging niche markets to invest in. To motivate her, she is in competition with a figure called "The Antagonist", which is strongly implied to be an AI. At the end of the story it's revealed that The Antagonist is not only a human being, but also her husband, and it is apparently SOP at the company they work for to pit married couples against each other. They remain Happily Married throughout.
  • 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 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 close 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. This is nothing to Athos, however, as he is still legally married to Milady by the time the book takes place.
  • 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....
  • Inheritance Cycle: 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.
  • Ayn Rand:
    • In The Fountainhead 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 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.
  • Occurs in the first two books of the Elemental Assassin 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 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 People's Republic of Haven in the Honor Harrington series of novels assigned Political Officers 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 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, 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.
  • C. L. Moore's Jirel of Joiry 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 Kiss of Death, 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 Please Don't Tell My Parents I'm a Supervillain, the villain Lucyfar (who claims to be the Archangel Lucifer) insists that she is dating the hero Gabriel (who she claims is the Archangel Gabriel). It's hard to tell if that's actually true or not. Gabriel says it isn't, but he doesn't try too hard to get rid of her when she 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 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".
  • In Widdershins Adventures, the titular thief Widdershins falls in love with the captain of the guard, Julian Bouniard.
  • Parodied in The Rules of Supervillainy where Gary Karkofsky is unwittingly the ex-lover of Ultragoddess (an Expy for Supergirl). His wife becoming a superhero also puts him as the Catwoman in their relationship.
  • Conan the Barbarian had several such relationships in the course of his long career. Conspicuous in the original Conan stories by Robert E. Howard is the relationship with the woman pirate Balit. She and Conan first fall in love with each other during a battle in which they face each other, sword in hand. Andrew Offut added The Sword Of Skelos where Conan has a prolonged love/hate relationship with the Zamboulan thief, spy and swordswoman Isparana. In a climatic scene Conan and Isparana are rolling on the desert floor, locked in what seems a mortal combat and try to kill each other - when suddenly the swords and daggers are thrown aside and they engage in intense love-making.
  • Bran Mak Morn, the Pict King, one of Robert E. Howard's lesser known characters, seeks revenge on Titus Sulla, the arrogant Roman commander who wantonly crucified a Pict. To get at the closely-guarded Roman, Mak Morn needs the help of the reptile-like "Worms of the Earth" who live in deep tunnels. And in order to make contact with them, he needs the help of Atla, a witch who is half-reptilian herself. Bran is rather repelled by her reptile side, and Atla herself is in no way fond of him - and makes it very clear. Nevertheless, her price for helping him is "to have one night of love with a King". He is willing to pay that price, along with many other things he is willing to do in order to get his revenge.
  • In Kushiel's Legacy, Phedre's brief liaison with Magnificent Bastard Melisande Shahrizai causes her no end of angst after Melisande betrays the nation; although they never rekindle their relationship, even when Melisande proposes it as part of An Offer You Can't Refuse, Phedre acknowledges that she has a weakness where Melisande is concerned. For her part, Melisande rues that she's picked up a bit of Phedre's conscience.
  • In The Perils of Enhancegirl, the titular character is drawn into a seductive game by the thief Ocelot. This trope is ultimately subverted. They briefly pursue a relationship, but Ocelot doesn't treat Sophie very well, manipulating her Aggressive Submissive tendencies, and eventually attempting to arrange the death of a romantic rival. She loses Sophie to that rival in the end.
  • The main premise of The Unexplored Summon://Blood-Sign is that Kyousuke used to be in a relationship with the White Queen, and the latter wants to rekindle this relationship at any cost. Though there are hints that, even in the present, it's not entirely one-sided. For example, Kyousuke still goes by the nickname "Alice with Rabbit", which was given to him by the White Queen to represent them always being together.
  • My Vampire Older Sister and Zombie Little Sister has a relationship between a member of the Bright Cross, a Creature-Hunter Organization, and Lilith, one of the monsters they aim to fight. They eventually got married, and are the father and stepmother of the main characters.
  • Carpe Jugulum: The antagonistic vampire Vlad de Magpyr is attracted to the witch Agnes Nitt, one of the heroes, because he can't read her mind due to her Split Personality. She, and particularly her other personality, can't entirely deny that he's attractive, particularly in the context of men not usually being too interested in Agnes. Still, she's too sensible to forget he's definitely a villain.
  • In Captain Freedom, the titular superhero dated future villainess Kaeko Katana while they were both at the Vineyard, and they've had an on-again-off-again relationship ever since. At one point, he tries to marry her, but it does not work out. At all.
  • Villains Don't Date Heroes!: This is most of the point of the series, especially the first book. Night Terror is the Anti-Villain who has conquered her entire city, then in comes the absolutely invincible Fialux, who blasts through all of Night Terror's defenses while Night Terror is still gobsmacked by how beautiful she is. By the end of the first book, they are officially dating, even if Fialux still dislikes Night Terror's methods.
  • Harry Potter: There are a few cases in Hogwarts of Quidditch players dating members of the rival House teams. In Harry Potter and the Prisoner of Azkaban, Harry (Gryffindor's Seeker) has a crush on Cho Chang (Ravenclaw's Seeker), and almost asks her out as his Yule Ball date in Goblet of Fire, but is beaten to it by Cedric Diggory (Hufflepuff's Seeker and Captain, and the legit Hogwarts champion for the Triwizard Tournament). Cedric and Cho keep their relationship going afterwards until Cedric's death at the hands of Voldemort. Harry does briefly date Cho in Order of the Phoenix and has his first kiss with her, but it ends after Cho's friend Marietta Edgecombe betrays the DA to Umbridge.

    Live-Action TV 
  • Jack and Nina from 24. Though all tension is gone from Jack's end and replaced with genuine hatred once Nina kills his wife..
  • 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 Sydney. Her attraction to Jack is clear... unfortunately, neither her love for Jack nor her daughter either of them, for that matter could overcome her addiction to Rambaldi's work.
  • Alphas: Gary and Anna, though neither of them have any real contempt for each other, and are more close friends than anything else.
  • On 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.
  • Downplayed in Babylon 5, where Vir Cotto helps Narns escape the Centauri occupation while his ditzy fiancee Lyndisty fondly remembers killing entire villages. Vir was less than thrilled with the setup; and Lyndisty is never heard from again after the single episode in which she appears.
  • While they are not the lead characters in Battlestar Galactica, the relationship of Captain Karl "Helo" Agathon and a Cylon copy of Lt. Sharon Valerii is suitably star-crossed. note  And despite the attempted gang-rape, demotions in rank, distrust, and Presidential baby-stealing, they are, as of the midpoint of season four, fairly happily married.
    • Until Boomer shows up and impersonates Athena.... Despite his near death in the finale, they get a happily ever after.
  • Batwoman (2019). Averted with Kate Kane; it's not unusual for costumed female villains encountering Batwoman to suggest they team up, but she's never interested and the dramatic tension of this trope is already being played out with her own sibling, the mad supervillain Alice. It's actually Crow Security agent Sophie Moore who finds herself in this position, making this a case of Dating Batwoman. This has a Surprisingly Realistic Outcome when Sophie gets suspended for helping Batwoman, and engages in a brief team-up and romantic fling only for Batwoman to break things off because she realises the relationship just won't work.
  • Birds of Prey (2002). 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.
  • Servalan and Avon from Blake's 7. 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.
  • In the setting of Buffy the Vampire Slayer, dating the enemy seems commonplace not only for Slayers, but their enemies too:
    • 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), though it is lampshaded when Buffy talks of how difficult it is to stake vampires when you're having fuzzy feelings for one.
    • The trope is deconstructed when Spike and Buffy get together in Season 6 — the result is a Destructive Romance, due to Buffy's self-loathing over the relationship and Spike's failure to understand Buffy's moral qualms, showing just how potentially harmful one of these relationships really could be. It's worth noting that Buffy doesn't have sex with Spike (at her initiation) until after she realizes that Spike's inhibitor chip no longer works and he could kill her.
    • Downplayed in Season 7, when Unresolved Sexual Tension and Undying Loyalty mostly replace the Destructive Romance and Belligerent Sexual Tension.
    • 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 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.
    • 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.
    • And there was "Wild at Heart", where Oz was into that other werewolf.
    • Buffy was actually wooed by Count Dracula himself in "Buffy vs. Dracula". In "The Girl in Question", 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 - or went along with it solely to screw with Angel and Spike.
  • Charmed:
    • Phoebe Halliwell and Cole Turner, although initially he was just trying to seduce her so he could kill her. He eventually turned good for a while.
    • One episode reveals that the girls' grandmother loved and was loved by a necromancer she fought. The real extent of their relationship wasn't exactly clear, but the entry she wrote on him in the Book of Shadows included his favorite wine and movie, and he was able to exercise some measure of control over her spirit because of their love, so they must have had some sort of relationship.
  • Gil Grissom and Lady Heather in CSI.
  • Cobra Kai: When Daniel LaRusso's daughter Samantha first dates Cobra Kai student Miguel Diaz in season 1, they have to keep their relationship a secret because Daniel would disapprove of his daughter dating a student from Johnny Lawrence's dojo. They break up after Miguel wrongly suspects Samantha of cheating on him with Johnny's son Robby, leading to Miguel accidentally punching Samantha during an altercation with Robby. Their second attempt at a relationship in season 3, the aftermath of the school rumble in the season 2 finale, goes over much more smoothly, helped by the fact that Miguel and Johnny have cut ties with Cobra Kai to start a new dojo called Eagle Fang. She and Miguel end up convincing the city council to let the All Valley Karate Tournament go on where her father and Johnny were unsuccessful at swaying the council, and convince their respective dojos to merge together to take down Cobra Kai. And after fighting off a Cobra Kai assault on the LaRusso residence, they end up being the ones to talk Daniel out of killing Kreese.
  • 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.
  • 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 take a bullet for her.
  • 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.
  • By series 6 of Doctor Who, the Doctor became romantically involved with a convicted murderer and psychopath raised to assassinate him. She succeeds more than once, but he keeps coming back for more. (Averted, though, in that very early on in their relationship (from her perspective) she changes allegiances completely, and her loyalty is absolutely and without question with the Doctor from there on out.) By that time, the show had already taken the existing Foe Romance Subtext between the Doctor and the Master up to full-blown text, with the strong implication that part of the reason why the Doctor fell for River so hard was because she reminded him of the Master while being actually redeemable.
  • 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, 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.
  • Mountie Fraser's doomed love affair with bank robber Victoria in Due South is a deconstruction. Turns out, it's really hard to have a healthy relationship with a bankrobber and murderer, especially if she has any hard feelings over you putting her in prison after falling in love.
  • Sherlock and Irene Adler, who is actually Moriarty, on Elementary. 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.
  • 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. Only if you don't count her flagrant bigamy — who hasn't she married?
  • In Season 2 of Gotham, 12-year-old Bruce Wayne has this going on with two girls: Selina Kyle, who works for the Gotham Mob, and Silver St. Cloud, who is trying to seduce Bruce on her uncle Theo's behalf; Theo wants to murder Bruce.
  • In Grimm Nick (a Grimm) and Adalind (a Hexenbiest) start a relationship which is kind of taboo for their respective kinds. Adalind does makes a Heel–Face Turn eventually.
  • Hannibal has Hannibal Lecter's intense feelings for protagonist Will Graham, feelings that start with lighthearted curiosity that evolve into an all-consuming love so powerful he'd rather get arrested and go to prison for three years rather than live a free life without Will. Will, on the other hand, feels that same intense feeling for Hannibal but is convinced it's feelings of friendship from their pure understanding of each other until he's flat out told otherwise. He eventually comes around, breaking Hannibal out of prison, joining him in the pack killing of Francis Dolerhyde, and accepting Hannibal's romantic affections... before throwing them both off a cliff. It's a complicated foemance, to say the least.
  • Kono's mystery boyfriend on Hawaii Five-0 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.
  • 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.
  • 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.
  • Xev and Prince, Lexx.
    Prince: Do you still feel anything for me?
    Xev: A little.
    Prince: You shouldn't.
  • Luke Cage (2016): A retroactive example in season 2. In high school, Mariah Dillard briefly dated Thomas Ridenhour. As adults, he went on to become a cop while she became a corrupt politician and eventually a crime boss.
  • Jack and Juliet from Lost. They started to develop feelings for each other before Juliet's Heel–Face Turn. Then later, in the 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 Heel–Face Revolving Door.
  • In The Man from U.N.C.L.E., Napoleon Solo apparently has an ongoing flirtation with Angelique, an agent of THRUSH.
  • In NCIS Ziva had a relationship with a crooked, alcoholic Mossad agent. It failed, spectacularly.
  • 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, Michael's switched sides, so this trope no longer applies and they revert to being a Battle Couple.
  • 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 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.
  • In Power, Angela Valdes is a federal prosecutor assigned to a taskforce to bring down a major cartel boss by catching and flipping his mysterious and anonymous New York distributor. Meanwhile, she's having an affair with her highschool sweetheart, James St. Patrick, who, unbeknownst to her, is the very distributor she's chasing.
  • Power Rangers:
    • 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 Luke, I Am Your Sister reveal, Andros the Red Ranger invokes My Sister Is Off-Limits! 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 his car. 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.
  • Helen Magnus and John Druitt of Sanctuary. They were engaged until Druitt acquired an Enemy Within and became Jack the Ripper. Now he alternates between helping and tormenting Magnus, but admits he still loves her. One episode implied she feels the same way.
  • Scandal: The beginning of Quinn's romantic relationship with Gideon, a cub reporter who seems on the verge of breaking the Amanda Tanner story. An especially tragic end, as Gideon dies and Quinn is effectively framed for the murder.
  • Sherlock: Irene and Sherlock.
  • Smallville, in the first of the three episodes Alicia appears in, the Clark/Alicia relationship is this trope. Afterwards, she's Reformed, but Rejected by all but Clark. And in Season 7, Oliver/Tess, though they only dated before they became hero/villain, and besides one booty-call, nothing else happens.
  • 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.
  • In Stargirl, Brainwave's wife was Merri, who was Starman's sister and a superhero in her own right (known as the Girl of 1000 Gimmicks). Unfortunately, after the destruction of the JSA and Starman's death, Merri had an argument with her husband, which resulted in him killing her.
  • 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). There's also Odo and the Female Changeling from Deep Space Nine.
  • Weird example. In the Star Trek: Deep Space Nine episode "Our Man Bashir", Bashir's character in a holodeck scenario, a James Bond expy, is in a relationship with a female KGB agent.
  • Supernatural: Most times where a villain takes an interest in one of the heroes it's just unidirectional Foe Yay. 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 Hemo Erotic territory when she lets him drink her blood, to which he is addicted. When he admits it to Dean, his brother is more than squicked out.
    • 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.
  • Teen Wolf: 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 Alpha Twin Ethan in a homosexual and supporting character version of this.
  • John Connor and Cameron in Terminator: 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.
  • 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...
  • Damon and Elena from The Vampire Diaries. Both in the series, and the books.
  • In Vegas 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 Christmas Episode 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.
  • 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. These two get a rare happy ending, as CJ quits politics despite an offer from President-elect Santos to go run a much-less-controversial charity initiative, and mentions that Danny is waiting for her at LAX "with a tub of sunscreen". A flash-forward at the beginning of season 7 shows them happily married with a baby on the way.
  • Wizards of Waverly Place: Justin and Juliet.
  • Xena: Warrior Princess: Xena and Ares.
  • Young Blades: Stuart and Jacqueline in "04 - The Exile".

  • 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.
  • Miike Snow's video for "Genghis Khan" is about a Bond villain-esque supervillain who falls in (eventually requited) love with his Tuxedo and Martini-style secret agent nemesis.

    Newspaper Comics 

    Professional Wrestling 

  • Played for Laughs in the radio comedy Revolting People which is set in Baltimore, Maryland in the years immediately before The American Revolution. One of the main subplots is a romance between the leader of the local revolutionary cell Mary, and Captain Brimshaw, the commander of the British soldiers stationed in town. However, since Baltimore is far removed from the actual revolution, Mary's revolutionary activities are basically just public annoyances, and Brimshaw is a slightly dim REMF who acts more like a barely-competent police chief than an occupier.

    Tabletop Games 
  • Nobilis: Nobles have shacked up with Excrucians on grounds ranging from "screw Lord Entropy, Love Redeems" to "someone told me not to". One Running Gag in third edition is that Jenna Moran (author) and Miranda Harrell (one of the artists) have...ambiguous relationships with the Excrucians Genseric Dace and Coriander Hasp, respectively.

    Video Games 
  • The Trope Namers Batman & Catwoman are at it again in Batman: Arkham City, providing the trope image. There wasn't quite as much flirting in their first meeting in Batman: Arkham Origins Blackgate, but you can tell where it got its start. By Batman: Arkham Knight, Batman decides it wouldn't work out, due to his decision to give up being Batman. He does sound genuinely heartbroken over it.
  • Something similar happens in Injustice 2. In Catwoman's arcade mode ending, she enters a committed relationship with Batman, but being plain old Bruce and Selina doesn't excite her as much; their relationship only thrilled her when it was Forbidden Fruit. Also, being a billionaire's girlfriend meant she'd never have to steal again. Getting everything she wanted bored her senseless. She ultimately leaves him to return to her old life.
  • In Batman: The Telltale Series you can romance Catwoman as Batman and even have sex with her at one point in Season 1. The Golden Ending of Season 2 has Batman tell her he loves her and secure her freedom from Amanda Waller and the Suicide Squad, but with the bankruptcy of Telltale Games it's unlikely we'll see the relationship progress further anytime soon.
  • 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. Then in the next game, it's back to business. Sort of.
  • Turns out that your love interest in Quest for Glory IV is a powerful vampire known as The Dark Master who wants to resurrect the local Eldritch Abomination.
  • 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-Gray 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.
  • Story of Seasons:
  • MegaMan Volnutt and Tron Bonne in Mega Man Legends, at least in terms of Ship Tease. While Tron clearly has a crush on Megaman, nothing ever comes of it by the end of the second installment, not partially because it ends with Megaman stranded on the moon.
  • A Steamy Romance Novel: Forbidden Love is a Vendor Trash item that can be read in World of Warcraft that details a romance between Marcus, an Alliance paladin, and a blood elf, the book clearly indicating that she's a loyal member of the Horde.
  • 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.
  • Assassin's Creed:
    • 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.
    • In Assassin's Creed: Unity, Arno Dorian's main love interest is his childhood friend Elise, a Templar who is the daughter of the recently-assassinated Grandmaster. He ultimately ends up choosing her over the Assassins, which leads to his mentor Bellec attempting to kill them both and him being expelled from the Brotherhood.
  • Otacon and Sniper Wolf in Metal Gear Solid. One-sided from him to her.
  • Dragon Age: Origins:
    • The Warden and Morrigan border on this: while on the same side, she's one of your more ruthless teammates and has her own agenda for following you.
    • Wynne mentions in party banter that she had a son. The Asunder novel reveals that the father was a Templar. World of Thedas: Vol II heavily implies that the Templar was Knight-Commander Greagoir.
  • 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.
    • Rival Romance in general can be considered this trope, since Rival Hawke is everything opposite of their love interest.
  • If neither are romanced, Dorian, a Tevinter Mage, and The Iron Bull, a Qunari from Dragon Age: Inquisition will be this.
  • Garen and Katarina in League of Legends, who quite literally got matched via a dating service, yet are champions of opposing countries. One's a noble and duty-bound knight, the other is a ruthless and bloodthirsty assassin, but they do have their similarities, most notably signature moves that involve lots of spinning. This carries over to the CCG spin-off Legends of Runeterra where their card interactions are... telling, to say the least.
    Katarina: I will slay you where you stand! (softly) Dinner, tonight?
    Garen: You shall fall on your folly! (whispers) Meet me at the south docks after dark!
  • Mass Effect:
    • Commander Shepard (Alliance) and Miranda Lawson (Cerberus) in Mass Effect 2.
    • 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 Wretched Hive, 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.
  • And yet another BioWare case: In Star Wars: The Old Republic, Lana Beniko (a Sith sorceress) and Theron Shan (a Republic spy) can be romanced, regardless of faction or gender of the Player Character. A Jedi dating Lana or an Imperial Agent flirting with Theron would fall into this category.
  • In The Elder Scrolls V: Skyrim, the Dawnguard DLC has a subtle Ship Tease between Serana of the Volkihar Vampire Clan and the Dragonborn, even if the latter chooses to remain aligned with the Dawnguard. However, Serana cannot be married unlike other follower characters, meaning the relationship never really progresses beyond platonic friendship.
  • Farta the Troll loves her masochistic counterpart, Eryi the Fairy, in Eryi's Action.
  • In Infernal, the banter between Lennox (the protagonist) and one of EtherLight's people, Major Elena Zubrov, implies this kind of relationship, but in reality, that's just because Lennox is being impertinent and Elena is playing along. It certainly doesn't turn into anything (given that Lennox eventually kills her and eats her soul).
  • Played for Laughs in Shantae, where Shantae and her Archenemy, Risky Boots, oscillate wildly between trying to kill each other and blatantly wanting to tumble in bed together.

    Visual Novels 
  • In Astoria: Fate's Kiss, you have Astraeus. During the Hades season 1 and 2 storyline, Astraeus is the villain. He's a Titan who is working to overthrow Olympus and the Top Tier Gods, and actually tries to kidnap your character on several occasions. In season 3, he is a romantic option himself.
  • In Destiny Ninja 2, from the Shall We Date? franchise, the heroine’s Evil Counterpart Mitsuru is a romance option. During his route, he winds up choosing his love for her over his ambitions.
  • Kohaku 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 Kohaku actually gets to have a happy ending. In the rest, she either continues bottling up her emotions (canon personality) dies or loses her memory, perhaps intentionally.
  • Umineko: When They Cry has Battler and Beatrice, whose romantic undertones are there, but not quite strong or obvious. However, in the end, it turns out that 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 not actually the real antagonist, but a faux one (although Battler believed she was the real antagonist for most of the series).
  • The Updated Re-release of Dengeki Stryker adds a route where the protagonist can starts a romance with Hilko from the Balbora empire.
  • In Shall We Date?: Ninja Shadow, this can potentially happen if Saori, a Sweet Polly Oliver member of a Vigilante Man group, dates either: Ritsu (a mix of Intrepid Reporter and Sympathetic Inspector Antagonist), Toru Nakagawa (the local Anti-Villain and Well-Intentioned Extremist) or Tsubaki Kusunoki (said Anti-Villain/Well-Intentioned Extremist's ally).
  • In Princess Evangile, this applies to Masaya should he choose to purse the members of the Red Rose Society, due to them opposing his entering into the all-girls Vincennes Academy.
  • In Ikemen Sengoku, this happens if the female main character chooses to romance one of the men opposing Nobunaga Oda, her landlord and employer — though in some of these routes, she doesn't know at first that the man she's becoming interested in is one of Nobunaga's sworn enemies.
  • In Heaven Will Be Mine, Saturn, Pluto, and Luna-Terra are technically enemies because of their allegiances to factions that are in opposition to each other, and they spend most of the game in conflict with each other, but that doesn't stop them from flirting — or even making out — with each other.
  • My Vow To My Liege lets the protagonist Fuchai romance Goujian, the king of the rival kingdom of Yue, her father's killer, currently her prisoner, and historically the one who conquers her kingdom and drives her to suicide. Whether she manages a happier fate than her historical counterpart depends on your choices.
  • Joy from Monster Prom apparently sleeps with Dmitri here and there, and Liam, who used to be the Big Bad of the Coven's show, is a former flame of hers. The sequel, Monster Camp, also reveals she's dated nearly all her former enemies.

  • Evil, Inc.:
    • Captain Heroic and Miss Match. There was also an affair between Commander Heroic and Flame long ago, and lately Lightning Lady and Elastic Man have developed a relationship.
    • Evil Atom's wife used to be a superheroine known as Star Force, she retired after the wedding, while he decided to found Evil, Inc instead of pulling off conventional supervillainy.
  • 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 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 webcomic) years between their scenes together. Damn you, Foglios!
  • Magick Chicks: Faith and her boyfriend, Ash, are the respective alphas at Artemis Academy and Apollo Academy, which are in competition with each other. Despite this, it's well known to both schools that they're dating, as they've even made out in plain sight of Faith's fellow students.
  • In Casey and Andy, 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. 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.
  • Sluggy Freelance:
    • Early on, Torg has this situation when he develops a crush on Val, who is revealed to be a vampire. Torg has to choose between joining her and remaining a good guy.
    • Torg also has a long-time ongoing alleged relationship with Oasis, a Brainwashed and Ax-Crazy Yandere. While he's initially attracted to her looks, the relationship mostly consists of his trying not to get himself or anyone else killed when she keeps showing up.
    • In "Girls' Night Out", the gang accidentally stumbles on the operations of a young crime lord called Tadius Greasenherr or Noah Zark. To get her friends out of his captivity, Zoë cooks up an Indy Ploy to pretend to be a criminal mastermind like himself. She also can't help noticing he's incredibly cute, even though she still mostly remembers he's a crazy villain, and by the end, he's also totally smitten with her (even if he thinks her name is "Kaka" due to some unfortunate stuttering). In a later story, they exploit this connection by having Zoë visit him again, keeping up the Diabolical Mastermind charade, and he's left even more impressed and smitten with her due to her seeming ingenuity.
  • 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.
  • In Everyday Heroes, Jane and Mr. Mighty 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, this didn't work well. Their relationship and subsequent marriage is implied to be the reason Mr. Mighty has been relegated to the lower tiers of super herodom.
  • The Order of the Stick:
    • 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
    • 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 the author had originally intended them to be love interests, but quickly realized that it wasn't happening.
  • 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. 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 King Radical, but there's still some romantic tension between the two.
  • The Young Protectors features a gay version of this with superhero Red Hot and supervillain the Annihilator.
  • 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 webcomic by Linkara, gives us the issue Masks, where Lightbringer's girlfriend Sandy is revealed to be the Scarlet Baroness, who's Breaking Speech on Secret Identity Identity throws Lightbringer off guard and forces his sidekick into pulling a Get A Hold Of Yourself Man.
  • In Dubious Company, Mary thinks she is this with Elly. Elly highly disagrees.
  • Questionable Content has Marigold and Dale, who play on opposing sides in World of Warcraft.
  • 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.
  • What's New? with Phil and Dixie once explored this in Magic: The Gathering-based soap opera comic.
  • Heroes of Inkopolis: Arnick, the straight-laced Inkling admirer of the Squidbeak Splatoon, and Tetrox, the devious Octoling. The fact that they live together in the same apartment along with being on the same team doesn't help either.
  • The superhero Falchion in Does Not Play Well With Others is dating his arch-enemy, except that neither he or anyone else except for her and the readers know this, because while doing villainy she disguises her gender by dressing in Powered Armor and using a voice changer to make her sound like a man. Out of the suit, she has Falchion and everyone else tricked into thinking she's the Mad Scientist's Beautiful Daughter.

    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.
  • In Chaos Fighters II-Cyberion Strike, 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 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 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.
  • In Tales of Wyre, Eadric becomes involved with Soneillon.
  • Whateley Universe: As could be expected from a series that deconstructs superheroism, there are several examples of this.
    • Vamp managed to wrap Skyhawk around her little finger with the same tricks she uses to make her johns think she's a 21-year-old prostitute who is great in bed (despite never actually having sex with any of them). This proved invaluable in getting her out from under the Necromancer's thumb, as he was able to get the evidence needed to clear her of a murder rap to the DA.
    • Black Diamond specializes in this, getting different superheroes in different cities to think they have this going on with her while she sets them up to do most of her dirty work for her - always making it look as if the hero 'won' in the end while still walking away with her real prize.
    • One of the reasons Imp accepts Lady Astarte's 'offer' of a teaching position at Whateley was because she didn't want to face falling in love with Superhawk (who admittedly isn't quite as dumb as Skyhawk... not quite.)
    • Paparazzi pulled this on Red Wing, but only as a ploy to blackmail him (as he didn't realize she was underage). Then, once he paid her off, she killed him.
    • Dragonblade isn't clear on the details of the relationship between his parents, the hero Shadowmage and the villainess Witch Queen, and he's happier not knowing.
    • Jadis Diabolik suspects something like this might have happened with her father and her unknown mother, whom she suspects was the superheroine The White Witch. While she used to imagine some romantic scenarios that might have led to them getting together, she has since taken less appealing, but far more likely, expectations of the circumstances. By 2016, she is using the last name "Frost", which may or may not indicate that she found out what really happened and is using her mother's surname.
  • Juno and Peter of The Penumbra Podcast. Of course, by season 3 Juno is officially a criminal himself, making this trope no longer in effect.

    Western Animation 
  • Ghost Princess and Clarence from Adventure Time. In life, GP was a warrior and Clarence was the leader of an invading army who referred to each other as "my love" even as they charged each other. Clarence accidentally killed her and spent the rest of his life as a depressed bum before dying himself. They met up as ghosts and (having forgotten their past), fell back in love. Finn deduced the circumstances of their deaths, but she forgave him and they passed on together.
  • Æon Flux and Trevor Goodchild, of course. They have been known to come face-to-face and suddenly start making out in the middle of a pitched battle, and there are some hints that the whole conflict between them is just an elaborate BDSM thing. Although one episode does reveal that Aeon would rather die than become nothing but Trevor's girlfriend. Thanks to Blue-and-Orange Morality, which of them counts as the villain in the relationship is debatable.
  • 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.
  • 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 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 me tell 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. However, in the follow-up comics, they did date, on and off, and remained good friends - Melanie even became a hero.
  • Batman: The Brave and the Bold
    • Naturally shown between Batman and Catwoman in several episodes. One even has them become a crimefighting team, having a child, retiring and finally dying together. However, 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 Death Trap, and when he asks why, she kisses him.
      "I see."
    • One episode also has Jonah Hex hooking up with Lashina, depicted here as a henchwoman of Mongul and Mongal.
    • Inverted with the show's version of Killer Frost, who became Firestorm's archenemy after Ronnie dumped her. By text.
  • Averted in the Batman series, Beware the Batman, with the title character's relationship with Magpie. He decided to visit her in prison to show her some sympathy she never received prior. Unfortunately, due to her already unstable mind, she mistakes his kindness with this trope, becoming a Yandere Stalker with a Crush.
  • In C.O.P.S., COP Sgt. Mace and Classy Cat-Burglar Nightshade had a romantic relationship despite being on opposite sides of the law.
  • Danny Fenton and Valerie Gray on Danny Phantom. In an interesting variation on this trope, only he became aware of this. She eventually ends their relationship on a It's Not You, It's My Enemies note, with Danny's superhero persona ironically being the enemy in question. For her part, Valerie doesn't learn that fact until the Grand Finale alongside everyone else.
  • Darkwing Duck 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, and come the comic book continuation, they're regularly dating.
  • Dave and Princess Irmaplotz in Dave the Barbarian.
  • The interactions with Scrooge and Goldie O'Gilt are pretty much that in DuckTales (2017), according to Word of God.
  • In one Justice Friends segment of Dexter's Laboratory, the heroes battle Comrade Red and his latest subsidiaries. One of them is a female brute named She-Thing, a Distaff Counterpart of Justice Friends member the Infraggable Krunk. She-Thing and Krunk fall in love quickly, and even the other members of both teams can't help but comment on how sweet it is, even though they're all in the middle of a heated battle!
  • El Tigre: The Adventures of Manny Rivera featured the titular character and Black Cuervo. The two went on two dates, 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, becomes rivals with Black Cuervo's civilian persona Zoe Aves... with whom Manny gets along with just fine and Word of God says he'll date again during high school. As a bonus, this is actually a familial trait: Black Cuervo's mother and grandmother (Voltura and Lady Gobbler) both had failed relationships with El Tigre's father and grandfather (White Pantera and Puma Loco) in the past, with the women still somewhat pining after them.
  • While not exactly a "hero", Professor Farnsworth of Futurama has some history with Mom, which resurfaces in a few episodes.
  • 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.
  • 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.
  • On The Grim Adventures of Billy & Mandy, paranormal exterminator Hoss Delgado winds up dating Eris, goddess of chaos.
  • 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.
  • In Krypto the Superdog, the whole Batman/Catwoman thing even extends to their respective pets, Ace the Bathound and Isis the cat.
  • Kung Fu Panda: Legends of Awesomeness
    • In 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. 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 for her. She returns in a later episode where she claims to have gone straight, but is actually planning to steal the artifact Shifu is delivering. It turns out she's being coerced by Junjie, and Shifu attempts to steal the artifact himself to help her. Mei Ling works with Po to stop him, then voluntarily goes to prison to protect Shifu's reputation.
    • 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 Scorpion was only getting close to him since he was catering a festival which she planned to poison the entire valley.
  • The Magician: Ace's love interest, Mona Malone, is also the daughter of his archnemesis, "Black" Jack Malone. Played with, in that she doesn't participate in her father's criminal activities.
  • Variation with Vanessa Doofenshmirtz and Monty Monogram from Phineas and Ferb. It's really their dads that are on opposite sides, but they have to keep it secret anyway.
  • Bob and Mouse's relationship in Reboot starts out as this but it doesn't last very long. Between Mouse's strong moral code making her a Classy Hollywood Hacker at worst, and her needing to team up with the heroes in the face of constant and ever-growing threats like the Web Invasion, Megabyte conquering Mainframe, and the supervirus Daemon, she ends up hanging around the good guys long enough for it to rub off on her and become one of their permanent allies.
  • The last season of Samurai Jack features Jack killing all the daughters of Aku, except for Ashi whom he eventually falls in love with. Sadly, in the last episode she literally fades away at their wedding.
  • 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!"
  • The Spectacular Spiderman has the usual heavy flirting (and one kiss) between Spider-Man and Black Cat. However, they part on less friendly terms after she blames him for her father, who is Uncle Ben's killer, refusing to break out of jail.
  • Spy Groove. Spy #1 finds himself falling for Sierra Nevada, who's brilliant, gorgeous and evil.
  • In Superman: The Animated Series brainwashed Superman and Lashina of the Female Furies.
  • 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.
  • 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...
    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 Transformers Animated, she became Optimus Prime's Catwoman. That is, once she gets over getting left behind.
  • Offered in TRON: Uprising. Impressed with how Beck (in his normal guise) managed to deal with an incident involving a Runaway Train, 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...
  • The Venture Bros. has murder machines extraordinaire Brock Samson and Molotov Cocktease back when they were both secret agents. It ends up being deconstructed as the series progresses: Despite all the flirting, Brock can't overlook Molotov's past misdeeds (including manipulating him into going rogue) and Molotov herself isn't willing to take things further with Brock and ends up dumping him for Monstroso. In the end, whatever relationship they could've had, just wasn't going to work out.
    • 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 thinks 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.
  • 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; 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 an Alternate Universe in the Marvel Multiverse where Kurt and Wanda did get together and they have a girl named Nocturne.)
  • 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 led to a considerable amount of character development for him later.
  • Young Justice has Red Arrow and Cheshire, just like the comics. After some one-sided flirting on Cheshire's part in the first season, they get married during the five-year Time Skip, only to split due to Arrow's obsession with finding the original Roy Harper. When Cheshire reveals they have a daughter, they get back together and have now reached Battle Couple status, complete with Cheshire carrying baby Lian around in a papoose while they kick ass. Both mother and daughter love it. Subverted by Season 3, where it's revealed Cheshire walked out on Roy and Lian due to being unable to give up her criminal lifestyle.

    Real Life 
  • Which one is the protagonist and the antagonist depends on your point of view, but American political strategists Mary Matalin (a Republican, and quite conservative) and James Carville (a Democrat and certainly rather liberal) faced each other across several elections in The '80s, 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. As of May 2016, this odd mismatch ended with Matilin revoking her Republican affiliation and joining the Libertarian Party, although it has nothing to do with Carville.
  • 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.
  • A lot of people, throughout history, were married to citizens of countries with which their own country was at war with. How they were treated varied a great deal from case to case. In some cases, that meant that they were forced to endure privations and difficulties. In other cases, the spouses were given no difficulties.
  • The banded mongoose (Mungos mungo) lives in tight-knit social groups that are extremely aggressive towards rival groups, engaging in ferocious territorial mob brawls that can easily result in deaths. Females in estrus, however, will frequently slip away from such battles in the company of an enemy male in order to copulate, thus averting the genetic risks of inbreeding. Biologists have even documented such females starting the fight specifically to distract their fellow group-members, so they have the chance to pair up with a nominal enemy without their relatives chasing him off.
  • H. P. Lovecraft hated Jews, even though he actually married one Sonia Greene, although their marriage only lasted two years.


Video Example(s):

Alternative Title(s): Foemance, Romance Between Enemies


Sly and Carmelita

Sly is a master thief and Carmelita is the Interpol operative tasked in catching him. They have come to an understanding over the years.

How well does it match the trope?

4.54 (13 votes)

Example of:

Main / DatingCatwoman

Media sources:

Main / DatingCatwoman