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  • The Atom: Reversed in the case of Ray Palmer, the Silver Age Atom. His wife Jean Loring became the villain Eclipso after their marriage and divorce... and after she went nuts and killed Sue Dibny and Jack Drake. His successor as Atom, Ryan Choi was dating Giganta. It was apparently a serious enough relationship that she took vengeance on his murderer.
  • Captain Atom: Captain Atom wound up marrying Plastique, a former Quebecois terrorist with explosive powers. Appropriately, in Justice League Unlimited she died in his arms, or at least she appeared to; she was never seen again but it was never confirmed if she truly died or not, while her comics counterpart is still alive and well.
  • Doom Patrol: In Doom Patrol (2016), Casey Brinke realizes her feelings for Terry None, the daughter of supervillain Mr. Nobody, while they concoct a scheme to destroy reality.
  • Green Arrow: Roy Harper (a.k.a. Speedy/Arsenal/Red Arrow/whatever they're calling him this week) was sent in by the Teen Titans to seduce batshit insane assassin Cheshire to get enough evidence to take her in. However, they fell in love with each other and Roy realized he wouldn't be able to do it and walked out... not knowing Cheshire was pregnant. Cheshire herself didn't find out who Roy was until it was all said and done, and decided to use Lian's existence to torment Roy as payback for leaving her. Roy gained permanent custody of Lian after Cheshire destroyed the country of Qurac for shits and giggles. While the two aren't together anymore and Roy knows how awful Cheshire is, there still seem to be lingering feelings between the two that Roy is having trouble processing, mainly because of how it all affects Lian. This constantly causes drama whenever Cheshire reappears in Roy's and Lian's lives. However, it's implied Cheshire is such a sociopath she's incapable of having real love for Roy and mainly exploits Roy's feelings to use him and screw with him. This is a woman who conceived a replacement baby when her daughter's well-being was used as a bargaining chip against her. It's also implied if Roy knew just how little Cheshire cared about Lian he'd want nothing to do with her, if not outright try to murder her for such disregard of Lian's life.
  • Green Lantern:
    • The Golden Age Green Alan, Alan Scott, not only fell in love with the villainess Thorn, he had children with her. Then again, he did fall in love with her good personality, Rose. His second wife, the Harlequin, also started out as one of his adversaries, although she was long reformed and retired by the time they married.
      • Making this trope happen is actually the entire reason Harlequin turned to crime. She wanted to catch Lantern's eye and decided that donning a sexy costume and alternately stealing things and teaming up with him would be the best way to attract his attention.
    • Likewise, the Silver Age Green Lantern, Hal Jordan, had Carol Ferris (whose Star Sapphire personality made frequent appearances) as a long-time love interest.
  • Justice League of America: In Final Crisis, Snapper Carr hooks up with the Cheetah.
  • Robin: In Red Robin, Red Robin was sort of dating the second Lynx, who was either a gang-leader or a Hong Kong cop undercover as a gang-leader. The irony that he was in a relationship with a possible villain in a cat mask was not lost on him.
  • Starman: This trope’s prevalence in the DCU is darkly deconstructed in James Robinson’s run; the Mist, Starman’s Archenemy, is an obsessive Yandere who’s so convinced that Starman secretly loves her that eventually she rapes him. Double Standard Rape: Female on Male is completely averted.
  • Superboy: Superboy dated New Goddess Knockout, under the impression she was a well-meaning thrillseeker, rather than a murderous sociopath.
  • Supergirl: (not the original, a shape-changing alien called Matrix) had a sexual relationship with Lex Luthor (who had put his mind into a cloned body of his younger self). She didn't know since Lex was posing as his own estranged son at the time.
  • Superman:
    • For a long time, Lois Lane was both Superman's primary love interest and one of his main antagonists. She was constantly trying to expose the fact that he was really Clark Kent, which would of course have wrecked his life. He had to work very hard to keep one step ahead of her, even as he was also drawn to her.
    • In the New 52 Batman/Superman book, after Kal-El loses his memories of ever meeting Batman and those of the Kent's lessons he and Selina begin a relationship before he (Superman) gains back those specific memories.
  • Watchmen: It is revealed that Night Owl II had a fling with Twilight Lady. It's not clear how far this went, though Dan keeps a framed picture years after retiring and seems deeply embarrassed when pressed for details. Before Watchmen: Night Owl reveals that the two did have a very, VERY sexual relationship, however brief and ultimately doomed.
  • Wonder Woman: During DC Rebirth, Bruce Wayne and Lex Luthor compete for the affections of Wonder Woman, to the point they start donating to one of her charities in an effort to get a date with her. Both men end up being outbid by Veronica Cale, who is worse than Bruce Wayne but not quite as evil as Lex Luthor, in this continuity anyway. Wonder Woman doesn't realize Veronica Cale is an enemy until midway through their date, however. Still, finding evidence Cale has been spying on and sabotaging her she vows to keep Cale on a tight lease and ends up shacking up with traditional love interest Steve Trevor after not being with him in the Post Crisis and New 52 continuities.

     Live-Action TV 

Live-Action TV

  • Batwoman (2019): Averted with Kate Kane; it's not unusual for costumed female villains encountering Batwoman to suggest they team up, but she's never interested and the dramatic tension of this trope is already being played out with her own sibling, the mad supervillain Alice. It's actually Crow Security agent Sophie Moore who finds herself in this position, making this a case of Dating Batwoman. This has consequences when Sophie gets suspended for helping Batwoman, and engages in a brief team-up and romantic fling only for Batwoman to break things off because she realises the relationship just won't work.
  • Birds of Prey (2002).
    • Inverted. Helena operates as an Anti-Hero sometimes verging on Sociopathic Hero and finds herself attracted to the good cop Reese.
    • The romance between Batman and Catwoman is a major aspect of the backstory, given that Huntress is their daughter, and is referenced in the opening credits.
  • Smallville: In the first of the three episodes Alicia appears in, the Clark/Alicia relationship is this trope. Afterwards, she's Reformed, but Rejected by all but Clark. And in Season 7, Oliver/Tess, though they only dated before they became hero/villain, and besides one booty-call, nothing else happens.
  • Stargirl: Brainwave's wife was Merri, who was Starman's sister and a superhero in her own right (known as the Girl of 1000 Gimmicks). Unfortunately, after the destruction of the JSA and Starman's death, Merri had an argument with her husband, which resulted in him killing her.

     Western Animation 

Western Animation

  • Batman Beyond: In "Dead Man's Hand", Terry McGinnis meets and starts to fall for a girl...who turned out to be Ten of the Royal Flush Gang. As the gang is arrested, Terry asks Bruce, "this kinda thing ever happen to you?" Bruce smiles. "Let me tell you about a woman named Selina Kyle..." Eventually the girl leaves her family's gang and gets a regular job and lifestyle; unfortunately she had betrayed Terry and Batman's trust once again before going straight, and Terry wasn't interested in leaving his steady girlfriend for her. As a conciliatory note, the end of the episode reveals that her actions convinced her brother to leave the gang as well so she's not entirely alone. However, in the follow-up comics, they did date, on and off, and remained good friends - Melanie even became a hero.
  • Batman: The Brave and the Bold:
    • Talia al-Ghul is depicted as a teenager in this version. Robin flirts with her in her first appearance, but she shoots him down. In her next, she frees Batman from a Death Trap, and when he asks why, she kisses him.
    • One episode also has Jonah Hex hooking up with Lashina, depicted here as a henchwoman of Mongul and Mongal.
    • Inverted with the show's version of Killer Frost, who became Firestorm's archenemy after Ronnie dumped her. By text.
  • Beware the Batman: Averted with Batman's relationship with Magpie. He decided to visit her in prison to show her some sympathy she never received prior. Unfortunately, due to her already unstable mind, she mistakes his kindness with this trope, becoming a Yandere Stalker with a Crush.
  • Justice League:
    • In one episode while he's being held prisoner by the Injustice League, one of Batman's moves to disrupt their unity is to seduce Cheetah... What is it with Bruce Wayne and cats, anyway?
    • A hint is dropped at the end of Unlimited's series finale when Giganta turns to kiss Flash before running away like the rest of the surviving villains. This plot thread was carried over to the official tie-in comic, where she faked a Heel–Face Turn in order to woo the Flash, who simply thought she had legitimately reformed. After finding out that Flash had a date with reporter Linda Park, Giganta gave up the charade and tried to kill them both.
  • Krypto the Superdog: The whole Batman/Catwoman thing even extends to their respective pets, Ace the Bathound and Isis the cat.
  • Superman: The Animated Series: A brainwashed Superman and Lashina of the Female Furies.
  • Teen Titans (2003): Cyborg starts dating Jinx when he goes undercover at the HIVE Academy, although it's the flirtatious Kid Flash who starts Jinx down the road to her Heel–Face Turn.
  • Young Justice (2010): Red Arrow and Cheshire, just like the comics. After some one-sided flirting on Cheshire's part in the first season, they get married during the five-year Time Skip, only to split due to Arrow's obsession with finding the original Roy Harper. When Cheshire reveals they have a daughter, they get back together and have now reached Battle Couple status, complete with Cheshire carrying baby Lian around in a papoose while they kick ass. Both mother and daughter love it. Subverted by Season 3, where it's revealed Cheshire walked out on Roy and Lian due to being unable to give up her criminal lifestyle.

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