History Main / DatingCatwoman

* In the ''Franchise/MarvelCinematicUniverse'' fanfic ''[[https://archiveofourown.org/works/31456490 The Artist's Garden at Madripoor]]'', Steve and Natasha go to [[Series/TheFalconAndTheWinterSoldier Madripoor]] in order to acquire the component they need for the [[Film/AvengersEndgame Quantum Tunnel]] from the [[JudgeJuryAndExecutioner Power Broker]], [[SamusIsAGirl who Steve is shocked to discover]] is [[FallenHero Sharon]]. While he's shocked and saddened by [[FallenHero her fall from grace]] and [[ItsAllMyFault blaming himself for it due to basically just leaving her behind]] [[DeconstructionFic after she threw away her career in the CIA to steal back his shield in]] ''Film/CaptainAmericaCivilWar'', 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.

* ''Film/{{Lifeforce}}''. The astronaut protagonist is obsessed with the beautiful space vampire he is hunting, even though to [[KissOfDeath touch her means death]]. They nevertheless make out several times. There's even a HoYay moment when he's driven to kiss her while she's [[BodySurf 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.

* In an episode of ''WesternAnimation/BatmanBeyond'', 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 ''FanFic/VoldemortGoesBackToSchool'', 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 [[DeathGlare "heated stares"]] and comes to the conclusion that he has a crush on him. HilarityEnsues.

* In ''Fanfic/TheInstituteSaga'', Characters/{{Superman|TheCharacter}} ends up dating Characters/{{Mystique}}.

[[caption-width-right:350:One man's fight is another man's date.]]

* In the ''Franchise/MarvelCinematicUniverse'' fanfic ''[[https://archiveofourown.org/works/31456490 The Artist's Garden at Madripoor]]'', Steve and Natasha go to [[Series/TheFalconAndTheWinterSoldier Madripoor]] in order to acquire the component they need for the [[Film/AvengersEndgame Quantum Tunnel]] from the [[JudgeJuryAndExecutioner Power Broker]], [[SamusIsAGirl who Steve is shocked to discover]] is [[FallenHero Sharon]]. While he's shocked and saddened by [[FallenHero her fall from grace]] and [[ItsAllMyFault blaming himself for it due to basically just leaving her behind]] [[DeconstructionFic after she threw away her career in the CIA to steal back his shield in]] ''Film/CaptainAmericaCivilWar'', he does find 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.

* Double Subversion in ''Fanfic/WithThisRing''. Renegade!OL invoked the trope to cover up that Cheshire was his informant and [[TheMole 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. [[spoiler: Cheshire and Renegade!OL become engaged.]]
** Both played straight (metaphorically) and averted (literally) with Batman, who is currently in a relationship with Talia al Guhl, daughter of Ra's. Both Selina Kyle (Catwoman) and OL think that Catwoman would be better for him.

* ''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. Averted, 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.]]

** This relationship is all but outright averted as of the remakes of ''[[VideoGame/ResidentEvil2Remake 2]]'' and ''[[VideoGame/ResidentEvil4Remake 4]]'', which recontextualize the portrayal of Ada and Leon's relationship into being predominantly between a manipulator and a reluctant pawn; filled with bitterness and distrust on Leon's side. He makes it gravely clear at the end of ''4'' remake that, given the choice, he would rather avoid having anything more to do with Ada unless necessary.

* Averted in the Batman series, ''WesternAnimation/BewareTheBatman'', with the title character's relationship with Magpie. He decided to visit her in prison to show her some sympathy she never received prior. Unfortunately, due to her already unstable mind, [[WrongGenreSavvy she mistakes his kindness with this trope]], becoming a {{Yandere}} StalkerWithACrush.

[[caption-width-right:300:One man's fight is another man's date.]]

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[[quoteright:300:[[VideoGame/BatmanArkhamCity https://static.tvtropes.org/pmwiki/pub/images/datingcatwoman.png]]]]
[[caption-width-right:300:One man's fight is another man's date.]]

* ''VideoGame/MaxPayne'' 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 CrookedCop who has no problem working with honorable criminals, not to mention that he spends more time in the series as a VigilanteMan 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 [[spoiler: execute a fellow police officer (who appears perfectly upstanding at that point) to save Mona]]. Likewise, Mona's an [[HitmanWithAHeart honorable hitwoman]] who refuses to kill good people, and she'd rather [[spoiler: 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.

-->'''Ada''': By the way... when are we going to carry on from where we left off that night?\\
'''Leon''': ''(half-smirking)'' Anytime but now.
** This relationship is all but outright averted as of the remakes of ''2'' and ''4'', which recontextualize the portrayal of Ada and Leon's relationship into being predominantly between a manipulator and a reluctant pawn; filled with bitterness and distrust on Leon's side. He makes it gravely clear at the end of ''4'' remake that, given the choice, he would rather avoid having anything more to do with Ada unless necessary.

* VideoGame/SlyCooper and Carmelita Fox. He's a heroic GentlemanThief, she's [[SympatheticInspectorAntagonist 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 [[VideoGame/Sly3HonorAmongThieves 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. [[spoiler: Then in [[VideoGame/SlyCooperThievesInTime the next game]], it's back to business. Sort of.]]

* Deconstructed in ''Fanfic/OneDayAtATimeFanfic'' with the {{Trope Namer|s}}. 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 ''Webcomic/DubiousCompany'', [[DarkChick Mary]] thinks she is this with Elly. Elly highly [[AllergicToLove disagrees]].
* In ''Webcomic/{{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 [[MoreThanMindControl relationship]] was...[[{{Fetish}} complex]].
* In ''Webcomic/EverydayHeroes'', Jane and Mr. Mighty [[https://eheroes.thecomicseries.com/comics/98 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, [[AgonyOfTheFeet 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.

* In an episode of ''WesternAnimation/BatmanBeyond'', 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 tet her loyalty, and gets a regular job and lifestyle; unfortunately she had betrayed Terry ''and'' Batman's trust once again before going straight, and Terry wasn't interested in leaving his steady girlfriend for her. As a conciliatory note, the end of the episode reveals that her actions convinced her brother to leave the gang as well so she's not entirely alone. However, in the follow-up comics, they did date, on and off, and remained good friends - Melanie even became a hero.

* Believe me, the ''WesternAnimation/DannyPhantom'' Fandom LOVES to ship Danny and Ember, who is an evil rocker ghost wanting to control the world via her hypnotic tunes. Though to be fair, Ember is smoking so...

* The ''WesternAnimation/TotallySpies'' fandom. A gender flipped example but for some odd reason, a popular paring is Sam and Tom Scam. I mean...EWWW! ONE'S A TEEN AND THE OTHER IS IN HIS 30s! What is the freaking appeal?!

* Sherlock Holmes and Irene Adler in ''Film/SherlockHolmes2009'' definitely have an air of [[UnresolvedSexualTension UST]] and there are [[NoodleIncident hints dropped]] of a previous relationship between them. Most Holmes adaptations follow this portrayal, although the original Irene Adler of "A Scandal In Bohemia" was technically not a criminal. In the [[Film/SherlockHolmesAGameOfShadows second film]], they kiss again and arrange a dinner date. Holmes is later shown to be [[spoiler:quite despondent over [[CollateralAngst her death at the hands of Moriarty]], and adds revenge to his motives for going after him]].

Kichikujima: Kaoru and Ami as well as later Takahisa and Mari.

* Rival UsefulNotes/{{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.

* ''WesternAnimation/TheIncredibles'': 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 TheCasanova Gamma Jack describes how difficult it is to fight attractive female supervillains. Downplayed in that Gamma Jack is also implied to be a [[FantasticRacism superhuman supremacist]] and thus [[SociopathicHero not a nice person]] at all.

* Sherlock Holmes and Irene Adler in ''Film/SherlockHolmes2009'' definitely have an air of [[UnresolvedSexualTension UST]] and Irene kissed him at one point (though he was drugged). Most Holmes adaptations follow this portrayal, although the original Irene Adler of "A Scandal In Bohemia" was technically not a criminal. In the [[Film/SherlockHolmesAGameOfShadows second film]], they kiss again and arrange a dinner date. Holmes is later shown to be [[spoiler:quite despondent over [[CollateralAngst her death at the hands of Moriarty]], and adds revenge to his motives for going after him]].