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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..."
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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.

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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.

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


Example Subpages:

Other Examples:

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    Anime & Manga 
  • 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.
  • Fairy Tail: It's eventually revealed that Fairy Tail founder Mavis Vermillion was not just an old friend of Zeref the Black Wizard, but was once his lover with whom he had a child. While they're enemies in the present, it's made clear that they still love each other when they come face-to-face in the Grand Finale.
  • Gundam:
  • Happy Kanako’s Killer Life: Detective Kazuo Takehara falls in Love at First Sight when investigating Kanako, who is the legendary assassin K that he’s trying to uncover. That fact doesn’t stop her from accepting when he asks her out on a date.
  • Kaitou Saint Tail and Asuka Jr.; in this case, the lead, a Phantom Thief that steals back stolen items, is the Catwoman-ish one.
  • This is the core premise of Love After World Domination. Fudō Aikawa, Red Ranger of the "Gelato Five", confesses his love to Desumi Magahara, one of the top generals of the evil organization Gekko, also known as "Reaper Princess". The two of them enter a Secret Relationship, which often involves them sneaking out for alone time while their respective teams fight each other.
  • 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 a 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 people's 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. Reconstructed with Luluco and Nova. He's an Empty Shell and The Mole, and as the Big Bad notes, her love is thus completely superficial. It's still strong enough to redeem him with a Care-Bear Stare.
  • 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 bare skin 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.

    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.
  • Bruce Has a Problem begins with Harley Quinn finding out Bruce's secret identity and falling in love with him. It says something about Gotham in general and the Batfamily in particular that this is an improvement for both Bruce and Harley.
  • Case Closed 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.
  • 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.
  • 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 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 straightforward than her one with Batman since Xander isn't bothered about her 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. To a lesser extent, shipping Nina with Coco is popular as well.
  • 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 over time 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.
  • In A Rabbit Among Wolves, 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 hitman 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 hitman 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 in the quotes section that when Selina and Bruce are dancing and they realize their 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").
  • In the cancelled Spider-Man 4, Peter was going to end up leaving Mary Jane for Felicia Hardy, who in this continuity was also the daughter of the Vulture. However Peter says in Spider-Man: No Way Home that he made things work with Mary Jane, meaning either the events of the cancelled films never came to pass and his bigger adventures stopped with Spider-Man 3 or it did happen and they moved past it.
  • 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 to save her from falling into 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.
  • Avengers: Infinity War: In the two years since Captain America: Civil War, Vision and Wanda Maximoff have secretly been meeting up for romantic holidays, even though Wanda is a fugitive and a member of the Secret Avengers, while Vision is a member of the New Avengers and part of his duties are trying to apprehend rogue superheroes.

    Music 
  • Blondie's "X Offender" is about a prostitute who falls in love with the police officer who busts her.
  • In the rock/metal opera project Aina: Days of Riding Doom, Syrius and Orianna fall deeply in love, despite being commanders of opposing sides in the war. And half-brother and half-sister. Not that they know it, to be fair.
  • Kirby Krackle's song "Then Again, Maybe Not" is sung from the point of view of a superhero who is a little tired of fighting his arch-nemesis, and suggesting that grabbing some Mexican food and flirty conversation would be a better idea.
  • 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.
  • Vices & Virtues by Reinaeiry is all about this trope, made for most enemies to lovers dynamics, sung from the view of the villain.

    Newspaper Comics 

    Professional Wrestling 

    Radio 
  • 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 operations. 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 Shop Fodder item that can be read in World of Warcraft that details a romance between Marcus, an Alliance paladin, and a Forsaken, 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. In fact, a scene of the Resident Evil: Damnation animated movie (which is part of the games' canon timeline) implies the two had something going on in the interlude:
    Ada: By the way... when are we going to carry on from where we left off that night?
    Leon: (half-smirking) Anytime but now.
  • Depending on how some players perceive exchanges between Karl Heisenberg and Ethan Winters in Resident Evil Village, their dynamic can be seen as this, particularly on Heisenberg's end. He writes about Ethan in his private journal and even describes him as having an "interesting body" rather than an "interesting medical condition", and his desire to defeat the Big Bad with him and help raise Ethan's daughter to achieve her full potential (albeit as a powerful weapon) is like a same-sex couple raising a child together. Ethan's refusal to team up with him and Heisenberg's shocked and disappointed outburst at it plays out like a person being rejected by their crush.
  • 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.
  • Potentially in Baldur's Gate II, depending on the character class:
    • Viconia, being a drow, nevertheless an evil drow that constantly comments with harshness and bitterness (not counting when she openly despises the weak or doing heroic deeds to assist them), would make a strange and rather unusual mate for a paladin... although you can try to make her alignment change to neutral during Throne of Bhaal;
    • And so Anomen, as a rigid Holier Than Thou lawful servant of Helm, would be a bit out-of-place for a chaotic evil charname;
    • After the Enhanced Edition, Hexxat and Dorn with a paladin charname would make Viconia look quite regular after all. Particularly buzzing if charname is of the specific kits of the undead hunter (Hexxat is a vampire) or the cavalier (specialized in fighting demons, and Dorn is a blackguard, that is, someone who made a pact with a demon in exchange for evil powers).
  • 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).
  • Shantae: Played for Laughs in that 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 start 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 pursue 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. This is deconstructed, as each ex was a toxic influence in Joy's life who she should have avoided like the plague. Even Girard, the most sympathetic ex, ruined the relationship as his evil acts in an attempt to impress her drove her away. Girard himself acknowledges that their differing morality was the reason things went south and he needs someone who is equally evil to make a new relationship work, which shows that this kind of relationship can suck for the evil party as well.

    Webcomics 
  • Cucumber Quest: Almond (a hero) and Peridot (a villain) have a rivalry with romantic tension. After being bested by Almond in their first encounter, Peridot becomes fixated on beating her and develops a crush, which takes the form of Tsundere behavior and concern with looking cool in front of her. Almond, meanwhile, enjoys teasing her. They enjoy facing off against each other and become friendlier over time, while still maintaining their rivalry. Peridot's romantic interest is very blatant; she'll go beet-red and turn into a flustered mess. Almond's is usually a lot more subtle, but is also apparent, such as the two blushing at each other with hearts around them when bonding over a common interest.
  • 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 superherodom.
  • 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 nor 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 Romance Subtext is 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 called Melanie... who turned out to be Ten of the Royal Flush Gang, and was struggling with loyalty to her family and her desire to have her own life, before settling on family loyalty. As the gang is arrested, Terry asks Bruce, "this kinda thing ever happen to you?" Bruce's crotchety facade breaks for once, he smiles and puts an arm around his shoulder, and says kindly, "Let me tell you about a woman named Selina Kyle..." Eventually the girl leaves her family's gang after finally being pushed too far by their manipulations to tet her loyalty, 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 an 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.
  • In She-Ra and the Princesses of Power, Catra and Adora have this type of relationship before Catra's Heel–Face Turn. A literal example, given that Catra is a Cat Girl.
  • 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 Spider-Man 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 (2003): 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 Romance Subtext 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 (2009) 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 than a friend. Wanda herself does love Kurt and it's admitted as such, but it's 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 (2010) 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 hero and the villain 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. 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.

 
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Alternative Title(s): Foemance, Romance Between Enemies

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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?

4.67 (18 votes)

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Main / DatingCatwoman

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