History Main / DatingCatwoman

* In ''Webcomic/EverydayHeroes'', Jane and Mr. Mighty [[https://web.archive.org/web/20201227193200/https://www.smackjeeves.com/discover/detail?titleNo=141697&articleNo=99 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.

* ''Manga/KaitouSaintTail'' has FoeRomanceSubtext between PhantomThief Meimi/Saint Tail and SympatheticInspectorAntagonist Asuka Jr., to the point Meimi actually starts falling in love with Asuka Jr. and starts thinking that [[PlayingHardToGet she kind of wants him to catch her]]. [[spoiler:It's subverted when he has a LoveEpiphany 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 [[LoveConfession 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]].

* ''Manga/KaitouSaintTail'' has FoeRomanceSubtext between PhantomThief Meimi/Saint Tail and SympatheticInspectorAntagonist Asuka Jr., to the point Meimi actually starts falling in love with Asuka Jr. and starts thinking that [[PlayingHardToGet she kind of wants him to catch her]]. [[spoiler:It's subverted when he has a LoveEpiphany 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 [[LoveConfession 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 compared to the fact he just really wants her to open up to him]].

* ''Manga/KaitouSaintTail'' has FoeRomanceSubtext between PhantomThief Meimi/Saint Tail and SympatheticInspectorAntagonist Asuka Jr., to the point Meimi actually starts falling in love with Asuka Jr. and starts thinking that [[PlayingHardToGet she kind of wants him to catch her]]. [[spoiler:It's subverted when he has a LoveEpiphany 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 [[LoveConfession confesses his love]] to her on the spot, and the part about her actually being a phantom thief is less concerning to him than the fact she won't open up to him to talk about it]].

* ''Manga/KaitouSaintTail'' has FoeRomanceSubtext between Meimi/Saint Tail and SympatheticInspectorAntagonist Asuka Jr., [[spoiler:although it's subverted when he has a LoveEpiphany specifically ''because'' he's started to suspect 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; in fact, it's implied that he'd been hoping that starting a relationship with her would get her to open up to him naturally so they could work things out in a less hostile context]].

* ''Manga/KaitouSaintTail'' has FoeRomanceSubtext between Meimi/Saint Tail and SympatheticInspectorAntagonist Asuka Jr., [[spoiler:although it's subverted when he has a LoveEpiphany specifically ''because'' he's started to suspect Meimi may actually be his "rival" and has recently been sympathizing with her actions to the point of not even really wanting to arrest her anymore; in fact, it's implied that he'd been hoping that starting a relationship with her would get her to open up to him naturally so they could work things out in a less hostile context]].

* Since ''Manga/PhantomThiefJeanne'' is heavily inspired by ''Manga/KaitouSaintTail'', 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 [[BecomingTheMask 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 SecretIdentity while Maron and Chiaki form a bond, but in the manga, Maron learns Chiaki's identity early and forms a deep relationship with him, with the potential DatingCatwoman problem only being one of the reasons she's afraid to fully make it a RelationshipUpgrade. [[spoiler:It's subverted when it turns out Sinbad was GoodAllAlong, and in fact his role as a rival to Jeanne was actually to prevent her from being an UnwittingPawn.]]

* Since ''Manga/PhantomThiefJeanne'' is heavily inspired by ''Manga/KaitouSaintTail'', Maron has a romance with Chiaki, who turns out to be Sinbad, the rival of her alter ego Jeanne. This is more pronounced in the anime adaptation, where Jeanne is completely unaware of Sinbad's SecretIdentity while Maron and Chiaki form a bond, but in the manga, Maron learns Chiaki's identity early and forms a deep relationship with him, with the potential DatingCatwoman problem only being one of the reasons she's afraid to fully make it a RelationshipUpgrade. [[spoiler:It's subverted when it turns out Sinbad was GoodAllAlong, and in fact his role as a rival to Jeanne was actually to prevent her from being an UnwittingPawn.]]

* ''Manga/KaitouSaintTail'' has FoeRomanceSubtext between Meimi/Saint Tail and SympatheticInspectorAntagonist Asuka Jr., [[spoiler:although it's subverted when he has a LoveEpiphany specifically ''because'' he's started to suspect Meimi may actually be his "rival" and has recently been sympathizing with her actions to the point of not even really wanting to arrest her anymore; in fact, it's implied that he'd specificially been hoping that starting a relationship with her would get her to open up to him so they could work things out together]].

* ''Manga/KaitouSaintTail'' has FoeRomanceSubtext between Meimi/Saint Tail and SympatheticInspectorAntagonist Asuka Jr., [[spoiler:although ironically he has a LoveEpiphany specifically ''because'' he's started to suspect Meimi may actually be his "rival" and has recently started to sympathize with her actions to the point of not even wanting to arrest her anymore; in fact, it's implied that he'd specificially been hoping that starting a relationship with her would get her to open up to him so they could work things out together]].

* Manga/KaitouSaintTail and Asuka Jr.; in this case, the ''lead'', a PhantomThief that steals back stolen items, is the Catwoman-ish one.

* Since ''Manga/PhantomThiefJeanne'' is heavily inspired by ''Manga/KaitouSaintTail'', Jeanne also has a romance with her main rival, [[spoiler: Chiaki aka Sinbad]]. Justified in the manga: [[spoiler: It turns out that the two are, in fact, [[Literature/TheBible Adam and Eve]]]].

* ''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 made out with a supervillain.

** In ''Videogame/AssassinsCreed'', the Assassin Altair and the Templar Maria end up falling in love, despite being enemies. This is shown in ''VideoGame/AssassinsCreedII'', 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 [[HeelFaceTurn switched allegiances]] in ''Assassin's Creed: Bloodlines'', and canonically the romance came afterwards.

* ''Fanfic/LessThanZero'' 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.

[[quoteright:300:[[Webcomic/GlitterAndGuilt https://static.tvtropes.org/pmwiki/pub/images/glitterandguilt_datingcatwoman.png]]]]
[[caption-width-right:300:Why bother trying to TakeOverTheWorld when you can just [[https://www.deviantart.com/rockybloo/art/Glitter-and-Guilt-Holding-the-World-944169240 hold it in your arms]] instead, eh?]]

[[quoteright:300:[[VideoGame/BatmanArkhamCity https://static.tvtropes.org/pmwiki/pub/images/glitterandguilt_datingcatwoman.png]]]]

[[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.]]

A SubTrope of OppositesAttract. Compare GoKartingWithBowser (when the relationship is platonic rather than romantic or sexual), LovesMyAlterEgo (for similar relationships between heroes and bystanders), and DefectingForLove (which happens when the Catwoman decides to go straight after all). Easily overlaps with VillainessesWantHeroes, TricksterGirlfriend, and AllGirlsWantBadBoys. May lead to TheMasqueradeWillKillYourDatingLife if the pairing is ultimately incompatible or too unstable. The one-sided version of this may be a VillainousCrush. See FoeRomanceSubtext for the less explicit version of this, and CriminallyAttractive when a criminal enters a romantic relationship with a law/government official, or their victim. See also LikesClarkKentHatesSuperman or related tropes, when they have different relationships inside and outside of a SecretIdentity. Compare {{Friendly Enem|y}}ies.

* ''Manga/FairyTail'': It's eventually revealed that [[spoiler:Fairy Tail founder [[BigGood Mavis Vermillion]] was not just an old friend of [[BigBad 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 GrandFinale]].

* In ''Webcomic/DubiousCompany'', [[DarkChick Mary]] thinks she is this with [[TheChick Elly]]. Elly highly [[AllergicToLove disagrees]].

* ''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 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.

* ''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 and government conspiracies, 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 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.

* ''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 and government conspiracies, 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 (whom he has no way of knowing is corrupted) to save Mona]]. Likewise, Mona's an 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.

* ''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 and government conspiracies, 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 to save Mona]]. Likewise, Mona's an 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.

* ''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 to save Mona]]. Likewise, Mona's an 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.