History Main / DatingCatwoman

* ''WesternAnimation/BatmanAndHarleyQuinn''. Faced with Batman's DisapprovingLook for sleeping with Harley Quinn, Nightwing mutters that he's not the only one of them who's slept with a supervillain.

* ''Film/AvengersInfinityWar'': In the two years since ''Film/CaptainAmericaCivilWar'', 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.
* ''Film/BatmanReturns'', which makes Catwoman a good bit more sympathetic, if somewhat more insane (she's [[spoiler:more in the crime business to get revenge on her murdering boss and knows she can't live with herself when it's over]]). You can see in the quotes section that when Selina and Bruce are dancing and they realize their other identities, they are very afraid.
* ''Film/BatmanAndRobin'': Robin believes he is doing this with [[Characters/BatmanPoisonIvy 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 [[LoveRedeems change sides]] so they can be together. Subverted, however, as Ivy is only pretending to love Robin to drive him and Batman apart and kill them with her KissOfDeath. [[spoiler: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.]]

* ''Film/Catwoman2004'' 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 "[[LovesMyAlterEgo I'm already seeing someone]]").
* ''Film/TheDarkKnightRises'' has this dynamic from early in the movie as Bruce shows a far more playful tone with Selina than his other enemies. Over the course of the movie, their mutual attraction slowly develops [[spoiler:and they ultimately end up creating new identities and leaving Gotham together]].

* In the [[WhatCouldHaveBeen/SpiderMan cancelled]] ''[[Film/SpiderManTrilogy Spider-Man 4]]'', Peter was going to end up leaving Mary Jane for [[Characters/BlackCatMarvelComics Felicia Hardy]], who in this continuity was also [[MadScientistsBeautifulDaughter the daughter of the Vulture]]. [[spoiler: However Peter says in ''Film/SpiderManNoWayHome'' 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 ''Film/SpiderMan3'' or it ''did'' happen and they moved past it]].

[[folder:Scripts]]
* In ''Script/JusticeLeagueMortal'', the romance between Batman and Talia al Ghul is a big aspect of the plot. In the backstory, Talia previously teamed up with Batman to take her out her father, Ra's al Ghul, out of her love for him. Bruce broke up with her later on, which drove her to team up with Maxwell Lord to gain her revenge against the Caped Crusader.
[[/folder]]

* The Trope Namers Batman & Catwoman are at it again in ''VideoGame/BatmanArkhamCity'', providing the trope image. There wasn't quite as much flirting in their first meeting in ''VideoGame/BatmanArkhamOriginsBlackgate'', but you can tell where it got its start. By ''VideoGame/BatmanArkhamKnight'', [[spoiler:Batman decides it wouldn't work out, due to his decision to give up being Batman. He does sound genuinely heartbroken over it]].
* In ''VideoGame/BatmanTheTelltaleSeries'' you can romance Catwoman as Batman and even have sex with her at one point in Season 1. The GoldenEnding of Season 2 [[spoiler:has Batman tell her he loves her and secure her freedom from [[Characters/SuicideSquadSupportStaff Amanda Waller]] and the ComicBook/SuicideSquad,]] but with the bankruptcy of Creator/TelltaleGames it's [[CutShort unlikely we'll see the relationship progress further anytime soon]].

* Something similar happens in ''VideoGame/Injustice2''. 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 ForbiddenFruit. Also, being a billionaire's girlfriend meant she'd never have to steal again. [[VictoryIsBoring Getting everything she wanted bored her senseless]]. She ultimately leaves him to return to her old life.

* In an episode of ''WesternAnimation/BatmanBeyond'', [[Characters/DCAUTerryMcGinnis 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, "[[ContinuityNod 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 test 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 do date, on and off, and remain good friends -- Melanie even becomes a hero.
* ''WesternAnimation/BatmanTheBraveAndTheBold''
** 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, [[spoiler:it was all just a book written by Alfred]].
** Talia al-Ghul is depicted as a teenager in this version. Robin flirts with her in her first appearance, but she shoots him down. In her next, she frees Batman from a DeathTrap, and when he asks why, [[PrecociousCrush she kisses him]].
--->''"[[TheComicallySerious I see]]."''
** One episode also has ComicBook/JonahHex 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.

* ''WesternAnimation/JusticeLeague'':
** In "[[Recap/JusticeLeagueS1E8And9InjusticeForAll Injustice for All]]", while he's being held prisoner by the Injustice League, one of Batman's [[PoisonousCaptive 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 "[[Recap/JusticeLeagueUnlimitedS3E13Destroyer Destroyer]]" when Giganta turns to kiss Flash before [[MercyLead running away like the rest of the surviving villains]]. This plot thread was carried over to the official tie-in comic, in which she fakes a HeelFaceTurn in order to woo the Flash, who simply thinks she's legitimately reformed. After finding out that Flash has a date with reporter Linda Park, Giganta gives up the charade and tries to kill them both.

* ''WesternAnimation/TheSpectacularSpiderMan'' has the usual heavy flirting (and one kiss) between Spider-Man and Characters/{{Black Cat|MarvelComics}}. However, they part on less friendly terms after [[spoiler:she blames him for her father, who is Uncle Ben's killer, refusing to break out of jail]].

* ''WesternAnimation/SupermanTheAnimatedSeries'' has this between a brainwashed Superman and Lashina of the Female Furies.
* ''WesternAnimation/TeenTitans2003'': Cyborg starts dating Jinx when he goes undercover at the HIVE Academy, although it's the flirtatious Kid Flash who starts Jinx down the road to her HeelFaceTurn.

* ''WesternAnimation/WolverineAndTheXMen2009'' does this with [[Characters/MarvelComicsNightcrawler Nightcrawler]] and the Characters/ScarletWitch. However, the relationship between them is difficult to define. Kurt cares about her and tries to steer her on the right path, yet never openly admits he cares about her as anything more 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; [[spoiler: in the end, Nightcrawler's charm finally seeps through and she rejects her father partly because of Kurt's influence, mostly because he was willing to sacrifice other mutants to achieve his ultimate goal]]. (Before anyone thinks this is completely out of the blue, there ''is''' actually an AlternateUniverse in the Marvel Multiverse where Kurt and Wanda did get together and they have a girl named Nocturne.)
* In ''WesternAnimation/XMenEvolution'', [[Characters/MarvelComicsKittyPryde 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.
* ''WesternAnimation/YoungJustice2010'' 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 TimeSkip, only to split due to Arrow's obsession with [[spoiler: finding the original Roy Harper]]. When Cheshire reveals they have a daughter, they get back together and have now reached BattleCouple status, complete with Cheshire carrying baby Lian around in a papoose while they kick ass. Both mother and daughter love it. 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.

[[folder:Web Original]]

* In an episode of ''WesternAnimation/BatmanBeyond'', [[Characters/DCAUTerryMcGinnis 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, "[[ContinuityNod 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 test 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.

* In ''WesternAnimation/COPSAnimatedSeries'', COP Sgt. Mace and ClassyCatBurglar Nightshade had a romantic relationship despite being on opposite sides of the law.
* Danny Fenton and Valerie Gray on ''WesternAnimation/DannyPhantom.'' In an interesting variation on this trope, only he became aware of this. She eventually ends their relationship on an ItsNotYouItsMyEnemies note, with Danny's superhero persona ironically being the enemy in question. For her part, Valerie doesn't learn that fact until the GrandFinale alongside everyone else.
* ''WesternAnimation/DarkwingDuck'' had the hero falling for 'evil businesswoman' Morgana, though she easily Heel Face Turned for both of the schemes she was in on because she felt the same way. She even knew his secret identity by season three, and come the comic book continuation, they're regularly dating.

* The interactions with Scrooge and Goldie O'Gilt are pretty much that in ''WesternAnimation/DuckTales2017'', according to [[WordofGod 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.

* ''WesternAnimation/ElTigreTheAdventuresOfMannyRivera'' featured the titular character and [[DarkActionGirl 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, [[GenkiGirl Frida Suárez]], becomes rivals with Black Cuervo's [[SecretIdentity civilian persona]] Zoe Aves... with whom Manny gets along with just fine and WordOfGod says he'll date again during high school. As a bonus, this is actually a ''[[GenerationXerox 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.

* The old Sunbow ''Franchise/GIJoe'' series had an episode with Joe computer specialist Mainframe falling in love with Dreadnok Zarana while the latter was undercover infiltrating GI Joe headquarters. In a rare example of continuity, this relationship became significant in a later episode.
* Rex and Circe from ''WesternAnimation/GeneratorRex''. And [[DeconstructedTrope both are finding out the hard way just how much heartache it can cause]]. Breach kind of forces her way into this trope with Rex.
* On ''WesternAnimation/TheGrimAdventuresOfBillyAndMandy,'' paranormal exterminator Hoss Delgado winds up dating Eris, goddess of chaos.

** In one episode while he's being held prisoner by the Injustice League, one of Batman's moves to disrupt their unity is to seduce Cheetah... What ''is'' it with Bruce Wayne and cats, anyway?
** A hint is dropped at the end of ''Unlimited'''s series finale when Giganta turns to kiss Flash before [[MercyLead running away like the rest of the surviving villains.]] This plot thread was carried over to the official tie-in comic, where she faked a HeelFaceTurn in order to woo the Flash, who simply thought she had legitimately reformed. After finding out that Flash had a date with reporter Linda Park, Giganta gave up the charade and tried to kill them both.

** 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. [[spoiler: Finally when he does start to feel for her she uses a mystical stone to swap bodies so disguised as Shifu she would trick Po and the Furious Five into robbing a vault for her. In the end, after everything is back to normal, Shifu sends her to prison. Which she escapes before arriving and runs off somewhere.]] The ending implies Shifu still having feelings for her. She returns in a later episode where [[spoiler: 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 [[spoiler: Scorpion was only getting close to him since he was catering a festival which she planned to poison the entire valley]].

* Bob and Mouse's relationship in ''WesternAnimation/{{Reboot}}'' starts out as this but it doesn't last very long. Between Mouse's strong moral code making her a {{Classy|CatBurglar}} {{Hollywood Hack|ing}}er 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 [[OmnicidalManiac 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 ''WesternAnimation/SamuraiJack'' features Jack killing all the daughters of Aku, except for Ashi whom he eventually falls in love with. Sadly, [[spoiler: in the last episode she [[WidowedAtTheWedding literally fades away at their wedding]]]].
* In ''WesternAnimation/SheRaAndThePrincessesOfPower'', Catra and Adora have this type of relationship before Catra's [[spoiler: HeelFaceTurn]]. A literal example, given that Catra is a CatGirl.
* Parodied on ''WesternAnimation/TheSimpsons'', when Bart has a Radioactive Man comic book in which the hero marries "Larva Girl". The issue's title is "To betroth a foe!"

* ''WesternAnimation/SpyGroove''. Spy #1 finds himself falling for Sierra Nevada, who's brilliant, gorgeous, and evil.
* In ''WesternAnimation/SupermanTheAnimatedSeries'' brainwashed Superman and Lashina of the Female Furies.

* [[HeelFaceTurn Until she eventually converted to his side]], Blackarachnia and Silverbolt had this kind of relationship in ''Franchise/{{Transformers}}: WesternAnimation/BeastWars''. True, she was originally a Maximal converted to the enemy's side via {{brainwash|ed}}ing, but still...
-->'''Blackarachnia''': I like being a bad girl. And you know something else? Somewhere deep beneath this squeaky clean armor-plating of yours, I think you like it too, hmm?
::For double points, they had this relationship in the sequel series as well but in reverse; Silverbolt's spark was in one of their foes and Blackarachnia was determined to convert him as he had converted her. To bring Blackarachnia into ''WesternAnimation/TransformersAnimated'', she became Optimus Prime's Catwoman. That is, once she gets over [[NoOneGetsLeftBehind getting left behind]].

* ''WesternAnimation/TheVentureBros'' 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 ([[spoiler:including manipulating him into going rogue]]), and Molotov herself isn't willing to take things further with Brock [[spoiler:and ends up dumping him for Monstroso]]. In the end, whatever relationship they could've had, just wasn't going to work out.

* ''Fanfic/TheManyDatesOfDannyFenton'': Danny unknowingly goes on a date with the Characters/{{Black Cat|MarvelComics}}, who flirts with him in and out of costume.

* Music/{{Blondie}}'s "X Offender" is about a prostitute who falls in love with the police officer who busts her.

* 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 [[RaginCajun James Carville]] (a Democrat and certainly rather liberal) faced each other across several elections in TheEighties, culminating in the 1992 campaign (in which Carville engineered UsefulNotes/BillClinton's winning strategy), still regularly appear across from one another on political debate shows, and call one another [[ArchEnemy arch-enemies]]. They not only dated but are ''married'' (getting hitched in 1993) and the proud parents of two daughters. They understandably do not talk politics at home. This odd mismatch ended with Matilin revoking her Republican affiliation and joining the Libertarian Party, although it has nothing to do with Carville.

* Offered in ''[[WesternAnimation/TronUprising TRON: Uprising]]''. Impressed with how Beck (in his normal guise) managed to deal with an incident involving a RunawayTrain, Paige suggests Beck look her up when they get back to Argon in order to "hang out", which Beck doesn't refuse. And this is on top of the FoeRomanceSubtext the pair already have going on...
* ''WesternAnimation/TheVentureBrothers'' 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 ([[spoiler:including manipulating him into going rogue]]), and Molotov herself isn't willing to take things further with Brock [[spoiler:and ends up dumping him for Monstroso]]. In the end, whatever relationship they could've had, just wasn't going to work out.