Dating Catwoman

aka: Romance Between Enemies

One man's fight is another man's date.^note Top from Batman/Fortnite: Zero Point, bottom from Batman: Hush

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

— Catwoman, Whatever Happened to The Caped Crusader?

When the hero of the show and one of the antagonists have a romantic tone 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 and Cop/Criminal Family (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 Criminally Attractive when a criminal enters a romantic relationship with a law/government official, or their victim. 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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Example subpages:

• Comic Books
  • The DCU
    • Batman
  • Marvel Universe
• Literature
• Live-Action TV

Other examples:

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.
• 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.
• In 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.
• One of the oldest anime examples is GoShogun, where the closest to an Implied Love Interest for the Action Girl Remy Shimada is none other than the villainous Leonardo Medici Bundle.
• Gundam:
  • Gundam ZZ has an unusual situation wherein the Lady of War Big Bad, Haman Karn, grows attracted to the much younger hero Judau Ashta. Judau displays some degree of concern for Haman, although how much of it was a romantic interest is open to debate. Judging by how the ladies get interested in him...
  • Team Chef Sai Saici and Plucky Girl Cécile (the sister of Gundam Fighter Hans Holgar) in G Gundam. Causes fewer problems than most examples, since Hans is no mortal enemy, but a decent, friendly Worthy Opponent in a sports tournament.
• 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 has Foe Romance Subtext between Phantom Thief Meimi/Saint Tail and Sympathetic Inspector Antagonist Asuka Jr., to the point Meimi actually starts falling in love with Asuka Jr. and starts thinking that she kind of wants him to catch her. It's subverted when he has a Love Epiphany specifically because he suspects Meimi may actually be his "rival" and has recently been sympathizing with her actions to the point of not even really wanting her to be arrested as a criminal anymore; he goes ahead and confesses his love to her on the spot, and the part about her potentially being a phantom thief is less of an issue to him than the fact he just really wants her to open up to him about her feelings.
• Kichikujima: Kaoru and Ami as well as later Takahisa and Mari.
• 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.
• 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).
• Since Phantom Thief Jeanne is heavily inspired by Kaitou Saint Tail, Maron has a romance with Chiaki, who turns out to be Sinbad, the rival of her alter ego Jeanne. Chiaki had actually been attempting to invoke this by seducing her and convincing her to quit being a phantom thief, only for things to go pear-shaped when he actually fell in love with her for real. This is more pronounced in the anime adaptation, where Jeanne is completely unaware of Sinbad's Secret Identity while Maron and Chiaki form a bond, but in the manga, Maron learns Chiaki's identity early and forms a deep relationship with him anyway, with the potential Dating Catwoman problem only being one of the reasons she's afraid to fully make it a Relationship Upgrade. It's subverted when it turns out Sinbad was Good All Along, and in fact his role as a rival to Jeanne was actually to prevent her from being an Unwitting Pawn.
• 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).
• 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:
  • Before becoming a Magical Girl in Codename: Sailor V, Minako had a crush on a sempai, who suggested she wear a ribbon in her hair. The sempai was a youma, and Sailor V's first kill. She still wears the ribbon (because she DID like how it looked on her).
  • Again in Codename: Sailor V, the Big Bad (and subordinate of Beryl's Dragon Kunzite) Danburite is revealed to be her actual first great love Kaitou Ace who was in love with her since their previous lives and apparently joined the villains just to get killed by her so she would become strong enough to keep going on.
  • Happens to her again in the anime, but in a FAR more Played for Laughs manner. One episode of Super S has her getting crushes on two guys and trying to date the two... Who are then revealed to be members of the Quirky Miniboss Squad of the season, and rather pissed at her for being two-timed. These two survive, however (not for her lack of trying, they just manage to dodge her wrath long enough to teleport away). For a while anyway.
• 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.
• Space Pirate Mito: Agent Mutsuki Nenga falls in love with Aoi while investigating him for his mother's crimes.
• 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 by combining "superhero romancing a supervillain" with Puppy Love in Tokyo Mew Mew. The half-monkey, hyper energetic Magical Girl Bu-ling and her bratty alien enemy Tart are each the "annoying kid" of their team and end up having a crush on each other after Tart saves Bu-ling from being killed by one of his own monsters.
• 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.
• In the Marvel Cinematic Universe fanfic The Artist's Garden at Madripoor, Steve and Natasha go to Madripoor in order to acquire the component they need for the Quantum Tunnel from the Power Broker, who Steve is shocked to discover is Sharon. While he's shocked and saddened by her fall from grace and blaming himself for it due to basically just leaving her behind after she threw away her career in the CIA to steal back his shield in Captain America: Civil War, he finds himself attracted to the new edge she displays and promises to do anything in his power to make amends to her, particularly getting her a long overdue pardon. Sharon likewise still has feelings for him despite everything that happened between them and the two are implied to have sex.
• Batman Beyond Revisited: Jake’s relationship with Inque became this for a short while before she joined the team.
• 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.
• 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.
• Danny Phantom fanworks:
  • Aside from the Danny/Valerie pairing, some fanfics have Danny paired up with Ember McLain.
  • 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 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.
• Death Note fanworks:
  • This is very common, as it has pairings such as Light (Kira, a Knight Templar Serial-Killer Killer) and L (the detective trying to catch him), Mello and Near (a mafia lord and a detective who are rivals), L and B (a detective and a Serial Killer), Naomi and B (again, a detective and a Serial Killer), even Light and Misa (which has the dynamic "I'll kill you if you are no longer useful" / "I'll kill you if you cheat on me"). In fact, Mello x Matt is the only popular ship in the Death Note fandom where both parties are completely on the same side and aren't trying to kill each other.
  • Light/Kira and L is the most popular ship. Here's a few examples of this trope in fanworks with Kira and L: A Cure for Love, Constant Temptation, I Won't Say, Office Politics, The Prince Of Death
  • All You Need Is Love ships Light and Naomi. They have "Victory Sex" once and Naomi ends up having Light's child, which she conceals from everyone. And that's the most normal thing that happens in that wonderfully bizarre and light fic.
  • Lampshaded in Fever Dreams when L gets him and Light some matching tracking devices which he uses when he keeps Light under house arrest and nicknames them "the wedding bands."
• In 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.
• Fates Collide: Shirou Emiya and Cinder Fall eventually fall in love and start dating, even though he knows she is a villain, but she eventually pulls a sort of Heel–Face Turn even if she doesn't change sides. This continues in the sequel Lost to Dust.
• 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.
• Lilgrimmapple's Gone Batty II: Eclipsed is setting Melody and Goth up for this after their Foe Romance Subtext in the first story.
• 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.
• Guys Being Dudes: The main couple consists of one of the leaders of Pokémon GO's player teams and an admin from the main antagonistic team.
• “Hijink” features Andy Sachs (The Devil Wears Prada) joining CONTROL after she is mistaken for Agent 99 (Get Smart), setting off a chain of events that reveals that Miranda Priestly’s daughter Cassandra is dating Heather, the daughter of former CONTROL Agent 23. The epilogue features the adult Cassidy and Heather, now working for CONTROL and KAOS respectively, officially acting in opposition but privately enjoying any opportunity to have even quick sexual encounters with each other.
• House Divided: Optimus Prime, an Autobot renowned as a hero for defeating the tyrannical Decepticon leader Megatron, falls in love with Megatron and has no small amount of serious moral struggles over their romance. In the end, though, they're able to be together after working as a team, along with Sari, to save Cybertron from the Quintessons and turning it into a safe haven for both Autobots and Decepticons to live in peace.
• Hours 'Verse: Conversed in My Kingdom for My Heart when the group watches Featherman during some downtime; Tatsuya wonders aloud about humanity's fascination with the hero and villain falling in love, and Maya rebuts that his own romance with Jun counts as this trope.
  Maya: This coming from the man who’s married to Black Condor, one half of the most famous hero/villain ship in all of Featherman!
  Tatsuya: That is not the same thing. Black Condor started out as a hero, and was manipulated and brainwashed into working for Lord Zero! He’s a victim, not a villain!
• 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.
• 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.
• 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 (Kenchi618) 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.
• 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 (Nyame) 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.
• 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.
• Played With in Run At The Cup. At the start of the story, Vi and Caitlyn are in what amounts to a "rivals with benefits" relationship. They are genuine rivals on the ice, but they have also been hooking up pretty much the entire time. Their rivalry fades once they're on the same team, and they eventually begin a genuine romantic relationship.
• 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.
  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.
• With This Ring:
  • Double Subversion. 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.
  • Played straight 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.
• Fans of Wander over Yonder have latched onto the relatively popular "Death Star" pairing involving the eponymous Wander and Lord Dominator, even though Dominator deeply resents Wander in canon and is one of the only villains he was unable to successfully redeem.

Films — Animated

• The Hercules version of Megara is a minion of Hades who sold her soul to him to save the man she loved (who subsequently dumped her for somebody else). She reluctantly helps him try to kill Hercules, but begrudgingly finds herself falling for his simple goodness.
• The Incredibles: One of the DVD extras is an explicit reference to this trope: In the background info on the Supers, there's an audio clip where The Casanova Gamma Jack describes how difficult it is to fight attractive female supervillains. Downplayed in that Gamma Jack is also implied to be a superhuman supremacist and thus not a nice person at all.
• Strange Magic: Both literal and figurative sparks start flying between Marianne and the Bog King when they start dueling each other. The fight ends with them panting and out of breath, staring at each other. Despite being the heir and ruling sovereign of their respective warring countries and that he kidnapped her sister, the two end up falling for each other.

Films — Live-Action

• 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.
• Buffaloed: Graham and Peg have chemistry, but he refuses to date her because he's trying to take down the city's seedy debt collectors and he's not sure if her business is clean or not.
• 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.
• 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.
• Lifeforce (1985). 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.
• 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 Joyeux Noël, the German lieutenant reveals that his excellent French is due to his French wife while their countries are at war.
• 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.
• 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.
• 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.
• 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.
• Played with in Sherlock Holmes (2009) and the sequel with Holmes and Irene Adler. There are hints dropped of a previous relationship and they definitely have an air of Unresolved Sexual Tension, but it's as if they're too busy one-upping and outwitting each other to act upon it.
• 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.
• In Spies, the good guy spy falls in love with the beautiful agent of the Nebulous Evil Organisation. They also turn out OK.
• 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.

Music

• 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.
• Blondie's "X Offender" is about a prostitute who falls in love with the police officer who busts her.
• 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.
• 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.
• PEGGY's song "Falling for the Villain" is largely this trope, as it's the internal thoughts of a hero as they slowly start to fall for the antagonist.
• 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

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

Professional Wrestling

• Faby Apache, usually a tecnica, periodically faced off against Billy Boy while he was a rudo. Neither their differing alignments nor status as opponents.
• Chyna and Mark Henry started their Belligerent Sexual Tension during the feud of their respective stables, D-Generation X and The Nation. Although the latter group was gone by the point they acted on it, reduced to the tag team of Henry and D'Lo Brown, those were still an enemy tag team.

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

• 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.
• 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).
• In Baldur's Gate III, it is possible to romance Shadowheart while being a Cleric of Selûne, the good goddess of light who contrasts Shadowheart's primordial goddess of darkness Shar. The backdrop of this unexpected love is very much an Enemy Mine — even though the two goddesses are mortal enemies, removing the Mind-Flayer tadpoles is more of a priority. However Shadowheart can eventually perform a Heel–Faith Turn when it is revealed that she was a brainwashed Selûnite, and eventually abandon Shar to embrace the true goddess who has been guiding her life. In fact, this is the only way to stay romanced to Shadowheart; if she pursues the path of evil then she cuts off the romance, considering you a distraction.
  Shadowheart: What's your game, exactly? A Selûnite bearing gifts sounds like a trick if I ever heard one.
  Tav: Just accept the gift and kiss me like you hate me.
  Shadowheart: (Said with a firm tone, but as "Shadowheart Approves" appears in the corner) Easily done! (Under her breath) How am I ever going to explain this in my prayers?
• 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.
• Dragon Age: Origins: 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.
• 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.
• 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).
• 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.
• 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.
• Max Payne and Mona Sax are downplayed examples. Though he's a cop and she's an assassin, they have never really been on opposite sides of each other. Max's a heroic Crooked Cop who has no problem working with honorable criminals, not to mention that he spends more time in the series as a Vigilante Man than a legit cop (the only game where he's a cop from start to finish is 2). When push comes to shove, he won't hesitate to execute a fellow police officer (who appears perfectly upstanding at that point) to save Mona. Likewise, Mona's an honorable hitwoman who refuses to kill good people, and she'd rather die betraying her employer (twice!) than let any harm befall Max. In a series where everyone is looking to betray everyone, Max and Mona stand out as the only two people unequivocally on each other's side.
• 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.
• 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.
• 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.
• 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.
• 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.
• Knuckles and Rouge from Sonic the Hedgehog fit this trope very nicely, especially in Sonic X.
• 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.
• Story of Seasons:
  • In Harvest Moon: Magical Melody you can marry your rival, Jamie, who is always the opposite gender from you. You and your rival are implied to be the canon pairing. Sadly, however, your game ends if you marry them, and you can't even find all the magical notes.
• 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.

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.
• Danganronpa V3: Killing Harmony: Kokichi seems to like this trope, given his Card-Carrying Villain status and heavily implied crush on Shuichi. His Love Hotel event involves him as a phantom thief and Shuichi as the detective who caught him.
• The Updated Re-release of Dengeki Stryker adds a route where the protagonist can start a romance with Hilko from the Balbora empire.
• 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.
• 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.
• 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.
• 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.
• 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.
• Shall We Date? franchise:
  • In Shall We Date?: Destiny Ninja 2, the heroine's Evil Counterpart Mitsuru is a romance option. During his route, he winds up choosing his love for her over his ambitions.
  • 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 Tsukihime, Kohaku is both the villainess and love interest during her route.
• Umineko: When They Cry has Battler and his witch Arch-Enemy 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. Subverted to an extent, 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). By the end of Episode 6, Battler and Beatrice are married and both stay in the side of good against Bernkastel for the rest of the story.

Webcomics

• 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.
• 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.
• 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.
• Ciem Webcomic Series: 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.
• 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.
• Demon King GF: The main plot of the comic is about a human hero summoned to protect humanity from demons being in love with the female king of all demons, who wishes to kill the hero and conquer humanity, and proposes to her. She accepts, if only to use their courtship to catch the hero alone and strike him down. However, she genuinely falls in love with him as the relationship evolves and soon settles down with him.
• 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.
• Erfworld: Wanda and Jillian arguably had such a relationship at one point. It must be said the Wanda was simply using magic to manipulate Jillian into being her unwitting servant. Their relationship was...complex.
• 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.
• 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.
• 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!
• Glitter and Guilt: The primary focus of the webcomic is the relationship between Sweetheart, a Magical Girl Warrior and defender of the city of Decking, and Bitterbat, an enforcer to the Big Bad who regularly invades Decking with his Quirky Miniboss Squad.
• 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.
• 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.
• 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.
• 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.
• 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.
• Questionable Content has Marigold and Dale, who play on opposing sides in World of Warcraft.
• 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.
• Super Stupor demonstrates this one played pretty straight...except that it's the morning after.
• The Young Protectors features a gay version of this with superhero Red Hot and supervillain the Annihilator.
• What's New? with Phil and Dixie once explored this in Magic: The Gathering-based soap opera comic.

Web Originals

• 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.
• In The Guild, Codex finds herself getting intimately involved with the leader of her guild's villainous rivals.
• 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.
• Eric had sex with Sister in Mall Fight 3, and remains on good terms with her. As much as one can be with Sister.
• 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.
• One of Shadow of the Templar's main plots is the developing relationship between FBI agent Simon Drake and Gentleman Thief Jeremy Archer.
• 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.
  • The gray-hat 'character assassin' Setup was on a job in Italy when she seduced the superhero Pugno Silenzio ('Silent Fist'), escaping before he realized who she was and how he had been duped. Years later, their children ended up rooming together at Poe Cottage, but when Pugno told his daughter (Striatura Blu, 'Blue Streak') who the mother of her roommate (Knockoff) was, Blu proceeded to harass Knockoff to the point that the school changed their room assignments. Later, during Parent's Day, Knockoff overheard her mother speaking to Pugno, telling him that he was Knockoff's real father.
• Catalyst: An angel and a demon went from loudly screeching at each other during a war to messy hate-sex to on-off couple. They broke up messily some time after Gray got promoted to archangel and Miss Eez became a demon overlord.

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 C.O.P.S. (1988), 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 in 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 has the hero falling for 'evil businesswoman' Morgana, though she easily Heel Face Turns for both of the schemes she's in on because she feels the same way. She even knows his secret identity by season three, and come the comic book continuation, they're regularly dating.
• Dave and Princess Irmaplotz in Dave the Barbarian.
• DuckTales (2017):
  • The interactions with Scrooge and Goldie O'Gilt are pretty much this, according to Word of God.
  • Fenton Crackshell-Cabrera (the heroic Gizmoduck) and Gandra Dee (agent of F.O.W.L.). She's set on defecting when the time is right and is also leaking info on their nefarious plans to him in the meantime.
• 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 features the titular character and Black Cuervo. The two go on two dates, though they do so for their own personal reasons. Whereas Manny Rivera/El Tigre becomes disenchanted with her when he discovers that she's just using him, Black Cuervo in turn develops 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.
• G.I. Joe: A Real American Hero has an episode with Joe computer specialist Mainframe falling in love with Dreadnok Zarana while the latter is undercover infiltrating GI Joe headquarters. In a rare example of continuity, this relationship becomes 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.
• In The Grim Adventures of Billy & Mandy, paranormal exterminator Hoss Delgado winds up dating Eris, goddess of chaos.
• Kaeloo: Kaeloo, the protagonist, and Mr. Cat, the main antagonist of the show, are in love with each other.
• 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 in 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!"
• In Sofia the First, Cedric's parents are a good wizard and Wicked Witch, who advise him to do good and evil respectively, even doing a Good Angel, Bad Angel scene in their first appearance. Despite this they appear to love each other and him.
• Spy Groove: Spy #1 finds himself falling for Sierra Nevada, who's brilliant, gorgeous, and evil.
• Transformers:
  • Until she eventually converts to his side, Blackarachnia and Silverbolt have this kind of relationship in 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 have this relationship in the sequel series as well, but in reverse; Silverbolt's spark is in one of their foes, and Blackarachnia is 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.:
  • 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.

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. They broke up for good in December 2017.
• 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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