Though DC Comics has attempted to romantically link their two most popular characters, there have been at least 10 toxic moments in the relationship between Batman and Catwoman. Making her first appearance in Batman #1, Selina Kyle, Buce Wayne's love interest and the notorious Gotham City burglar, was referred to as simply, "The Cat." As Catwoman burglarized the homes of the rich, Selina dressed herself up in a one-piece costume and carried around a nasty whip. Because the two found themselves on opposite sides of the law, Batman and Catwoman couldn't resist their seductive attraction and wanted more out of each together.
There were times when even the dark knight couldn't trust the elusive cat burglar, because Selina did not want to be turned down and domesticated by a personal relationship. Though they were adversaries many times, Selina realized she wanted to be less of an opponent and more of an intimate companion. Unfortunately, Bruce Wayne has a difficulty time letting go of the past and moving on from his parent's murders. Ever since the deaths of Thomas and Martha Wayne, Bruce swore he would never give up on the pursuit for vengeance and justice.
During writer Jeph Loeb and artist Jim Lee's Batman: Hush, Tommy Elliot revealed he had convinced Dr. Jonathan Crane, aka Scarecrow, into fixing up his fear serum. Because he inhaled the toxin, Batman thinks he is truly in love with Catwoman, but his romantic feelings have been manipulated. While Catwoman was trying to plant her lips on his, Batman physically pushed her away. Catwoman is absolutely angry that Batman would rather trust the twisted lies of a maniacal enemy than believe in her real feelings for him. Batman would rather risk denying himself true love than letting Hush win in the end.
9 The Wedding
The scheduled wedding between Batman and Catwoman was supposed to take place in writer Tom King and artist Mikel Janin's Batman #50. Before their wedding day, Selina Kyle had earned the trust of Superman and made a new friend with Clark Kent's wife, Lois Lane.
But there was something nagging within Selina's mind that forced her to leave Bruce standing alone at the altar. Selina believes that if she were to marry Bruce, that would actually be the end of Batman. Selina proved she didn't love Bruce as she left a letter for him to read.
8 Miss Kitka
Based on the hit TV Show, Lee Meriwether's portrayal of Catwoman in Batman demonstrates how the antagonist can play with the hero's heart. Smitten with Soviet Reporter Miss Kitka, Bruce (Adam West) found himself quoting poetry during their romantic date. Completely entranced by his feelings for Kitka, Bruce doesn't realize he was being played by Catwoman and gets kidnapped by the United Underworld. While Catwoman pretends to be tied up, Bruce's heroic fight with the kidnappers is faked and staged by her. When Catwoman is finally unmasked, Robin (Burt Ward) apologizes after witnessing the quiet heartbreak on Batman's face.
7 They're Always Fighting
In Batman Returns, the caped crusader and the cat burglar ended in physical fights that left each other bleeding. During their steamy encounter, Catwoman (Michelle Pfeiffer) teased touching his chest, while really searching for a weak spot in the kevlar suit. After Catwoman stabbed him with her claws, Batman (Michael Keaton) punched her face and threw her off the roof. During their dance at Max Shreck's costumed ball, Selina and Bruce were in utter shock as they finished each other's sentences. Now knowing each other's secret identity, Selina immediately thought the worst and assumed they would have to start fighting again.
6 New 52
During the New 52 era, writer Judd Winick and artist Guillem March's Catwoman #1 twisted the love-and-hate relationship into a sexual affair. Though Batman knew the master thief was in danger, he allowed the angry gangsters to destroy Selina's home after they uncovered her secret identity. During their verbal sparring, Batman argues that all her dangerous risks lead to an unavoidable end. Because she is an adrenaline junkie, Batman worries she wants to come close to death. Selina sees herself as emotionally unstable and volatile because she is possibly suicidal and determined to die.
5 Trail of the Gun
In writer Ann Nocenti and artist Ethan Van Sciver's Batman/Catwoman: Trail of the Gun followed the two as they searched nonstop for a smart gun that fired heat-seeking bullets. The story looked at different viewpoints in the debate about gun control and gun violence. As a young boy, Bruce Wayne witnessed a mugger brutally killing his parents with a gun. A murderer at heart, Selina was haunted by the memories of an abusive stepfather. If she had a gun at that young age, Selina would have definitely put a bullet into his head and killed him.
4 Switching Sides
In The Dark Knight Rises, Selina Kyle (Anne Hathway) was unpredictable to whoever her loyalty sided with. Secretly working for Bane (Tom Hardy), Selina directly led the Batman (Christian Bale) into a deadly trap. Refusing to help, Selina watched from the sidelines as Bane beat the Batman to a pulp before finally breaking his back. Refusing to show any more allegiance to Bane, Selina sided with the dark knight to stop the nuclear bomb from exploding. Because she only works for those who benefit her, the Cat argued with Batman over his self-sacrifice, something she would never do.
3 Cheating Hearts
In writer Tom King and artist Joelle Jones' "Superfriends" arc, Bruce Wayne's faithfulness to Selina was tested after they were engaged as a couple.
Though Bruce Wayne was in love with Selina, Batman has always had a stronger admiration for Wonder Woman. While Selina was anxiously waiting for Bruce's return to Gotham, Batman and Wonder Woman were living together in The Realm for more than 37 years. With Selina far away, the two bonded together over time and were mutually attracted to each other. Deep down inside, Selina knew Bruce cheated on her.
In writer Chuck Dixon and artist Greg Land's, Nightwing #52, Dick Grayson has a secret about Selina that he wouldn't want his adoptive father, Bruce, to know about. Nightwing and Catwoman found themselves crossing paths when she decided to steal the Klopmann Diamond. During a shootout, Nighwting was unable to keep his hands off of Catwoman and he planted his lips against hers. In reality, Catwoman started their sexual affair because she wanted to make Batman jealous. Willing to ruin Bruce's relationships with others, Catwoman desperately wants Batman all to herself.
In writer Tom King and artist Mitch Gerard's "Rooftops" two-parter, Batman has to bring in Catwoman to the police for the mass murder of 237 innocent lives. Rather than tell Batman the truth, Selina would rather have everyone believe she committed those crimes than squeal on her companion, Holly Robinson. After her orphanage was brunt down, with everyone inside dead, Holly sought revenge and killed those responsible for the terrorist act. Because Selina didn't tell the truth, Batman wound up with a knife in his throat after Holly thought he came looking for her.