The eternal battle between superheroes and supervillains defines the entire superhero genre and has been the source of countless stories. In both DC and Marvel Comics, heroes constantly fight to protect the innocent and uphold the law against immoral villains. However, not every confrontation between a costumed crimefighter and criminal ends in violence. In fact, there are a significant number of times when superheroes have dated the villains that they’re supposed to be fighting. Naturally, the quality of these relationships varies drastically from toxic to surprisingly healthy, although heavily tending toward toxicity. While it doesn’t always end well, these superheroes decided to let love blossom with their villainous rivals.
Superhero comics oftentimes have plenty of romantic drama, and what’s more dramatic than two people having an attraction for each other but being on opposite sides of the law?
With the ability to drain the life of anyone who touches her, Rogue has arguably the most difficult love life of any X-Man. Even with her longtime mutual attraction with Gambit, Rogue’s insecurity over her powers’ effect on people had proved a straining part of their relationship. Rogue eventually discovered that one mutant had an ability that allowed her to experience genuine physical contact: Magneto. Despite being the X-Men’s archnemesis and being several decades older, Magneto caught Rogue’s attention when they had to work together to survive in the Savage Land. The two would become an official couple many years later, and Magneto even proposed to Rogue. However, Rogue rejected the proposal and broke up with Magneto because she didn’t feel ready for marriage yet. Outside of the main continuity, Rogue and Magneto got married in the Age of Apocalypse timeline and dated in the hit X-Men ’97 animated series. This was a strange and controversial couple, but at least they parted on good terms and are now both X-Men.
There are few characters in comics with a more complicated and tragic love life than Wolverine. Many of Wolverine’s love interests end up dead, but one relationship saw him with someone with just as complicated a love life as himself. In 1921, Wolverine met iconic X-Men villain Mystique, and the pair had what could be best described as a Boonie and Clyde-style relationship as they stole and scammed. The two would work together on several jobs and date, but like most of Wolverine’s relationships, it ended poorly. In a demonstration of the shallowness of their relationship, Mystique pushed Wolverine off a train and abandoned him to keep all their stolen earnings. Since then, while Wolverine and Mystique may have the occasional one-night stand, it never becomes anything serious. Instead, the pair for the most part have become hateful exes who have fought each other countless times on behalf of the X-Men and Brotherhood of Evil Mutants, respectively. Underlining their estrangement, Mystique would even go on to have a relationship and a child with Wolverine’s archnemesis, Sabretooth.
The Golden Age Green Lantern Alan Scott has been in a relationship with not one, but two villains that reflect the character’s evolution. Originally, Alan married a woman named Rose Canton, who possessed an evil split personality called the Thorn with the power to manipulate plant life. Although Rose soon ran away from Alan to protect him from her evil personality, she still ended up giving birth to twins who would grow up to become the superheroes Jade and Obsidian. Infinite Frontier added a new aspect of Alan’s character by revealing that he was a closeted gay man. A prequel comic showed that before meeting Rose, Alan had a secret relationship with a man named Johnny Ladd until he seemingly was killed. However, not only was “Johnny” alive, but he was actually a Russian spy named Vladimir Sokov and a supervillain known as the Red Lantern. While Vladimir did have feelings for Alan, his loyalty to his country and internalized homophobia meant that the two could never be together. In both cases, Alan’s relationships ended in heartbreak and betrayal.
Given the sheer number of women that billionaire playboy Tony Stark has been with, it was practically inevitable that he’d end up dating a supervillain. Whitney Frost, aka Madame Masque, is the daughter of the supervillain Count Nefaria and she inherited his criminal empire. After suffering extreme facial scarring, Masque believed herself to be unlovable and began wearing a mask to hide her appearance. Yet, when Tony showed her kindness even after seeing her true face, Masque became infatuated with him, and they began a loving relationship. Even when they discovered each other’s secret identities, they still kept dating. Madame Masque became an important ally of Iron Man and helped him with both his crimefighting and business operations. Unfortunately, Masque’s loyalty to her father and connection to the criminal underworld ultimately led to her to betray her boyfriend and attack him. Since then, Madame Masque has dedicated her life to being Iron Man’s sworn enemy.
When Green Arrow’s protégé, Roy Harper, aka Arsenal, quit being the Emerald Archer’s sidekick, he went to work for the government and eventually found love. As a member of the anti-terrorist group CBI, Arsenal was sent undercover to gain the trust of the notorious mercenary and assassin Cheshire. Although Arsenal’s mission was to get Cheshire arrested, he soon fell in love with her, and the two had an affair. After his deceit was uncovered, Arsenal let her go without realizing that she was pregnant with his child. When Cheshire gave birth to Lian, she left her with Arsenal knowing that he’d be a much better parent. Their paths would cross several times as enemies, but Arsenal would always let Cheshire go free. The pair would become closer when Lian was thought dead, and when she was revealed to be still alive several years later. While most of the time they’re separate, Arsenal and Cheshire do love each other, but their loyalties to their respective sides of the law keep them apart.
Spider-Man has had his fair share of iconic relationships, from Gwen Stacy to Mary Jane Watson. However, he’s also had a consistent will-they-won’t-they style relationship with the notorious cat burglar Black Cat. Almost immediately from their first meeting, Black Cat began flirting with the Wall-Crawler. While at first the dalliance was more to distract Spider-Man so that she could get away with all the valuables she had stolen, over time she developed real feelings. These feelings, along with her willingness to play both sides, led Black Cat to become a more heroic figure and team up with Spider-Man numerous times. However, Black Cat was always more attracted to Spider-Man, and not Peter Parker. Still, after Peter’s marriage to MJ was retconned, he began having an on-again, off-again relationship with Black Cat. No matter what, it seems that Peter and Black Cat are doomed never to be a fully committed couple because Black Cat strangely has an aversion to being in a healthy relationship.
Daredevil has had several complicated relationships, and most of them end in disaster. His most iconic love interest clearly is Elektra. Before Daredevil became a hero and Elektra became an assassin, they were college lovers. Unfortunately, after the death of her father, Elektra dedicated her life to becoming a ruthless killer. When Daredevil and Elektra reunited, they were enemies—contract killing apparently does not form a good basis for a healthy relationship. However, after discovering Daredevil’s secret identity, Elektra became a more heroic individual. Still, the couple is nearly constantly at odds because Daredevil vehemently hates killing while Elektra lives for it. Elektra wasn’t the only villain Daredevil dated, as he also unknowingly had a relationship with the psychotic telepath Typhoid Mary. By using her innocent split personality, Mary Walker, to seduce and date Daredevil, Typhoid Mary was able to ambush the hero. Needless to say, while they oftentimes fight over the morality of killing, Daredevil’s heart will always belong to Elektra.
Shockingly, it was Carol Ferris’s love for Hal Jordan that turned her into a villain in the first place. Hal had a close relationship with Carol even before becoming Green Lantern. He worked for Carol’s aircraft company and the two eventually started dating. Unfortunately, everything changed, as it must, when the alien race known as the Zamarons chose Carol to be their queen and gave her the Star Sapphire gem because her love for Hal was so strong. The gem corrupted and twisted Carol’s feelings, brainwashing her into becoming the supervillain Star Sapphire who constantly sought to destroy her boyfriend. It would take several decades for the Zamarons, and by extension Carol, to reform and use the violet energy of love to make the universe a better place. Once they got back together, Hal even popped Carol the question. And while Carol initially said no, it was only a temporary refusal to allow them time to reunite from an intergalactic mission. After which, they planned to make the engagement official. So far, Hal and Carol are the closest any hero and villain have gotten to a happily ever after.
The X-Men are well-known for the sheer amount of romantic drama that happens in their comics, and Cyclops is the primary source of these plotlines. Cyclops’ main love will always be Jean Grey. Even when she became the multiversal genocidal maniac known as the Dark Phoenix, he did everything he could to save her. Notably, Cyclops would also have a relationship with Jean’s clone, Madelyne Pryor, who was created by the villain Mr. Sinister. Although Cyclops and Madelyne were happily married and even had a son together, when the real Jean returned and Cyclops rekindled his relationship with her, Madelyne’s mind snapped, and she became the nefarious Goblin Queen. Last and certainly not least, Cyclops had an affair with former member of the Hellfire Club Emma Frost and the two eventually had an official relationship. Obviously, Cyclops has a thing for telepathic women who will sometimes use their powers for evil.
No superhero in all of comic book history is more famous for their relationships with supervillains than Batman. Since the 1940s, Batman and Catwoman have been one of the most iconic couples in all of DC Comics. Their undeniable chemistry constantly conflicts with the fact that they’re on either side of the law. Batman’s heroism inspired Catwoman to become an anti-hero, and the two even nearly got married until she left him at the altar. Of course, Batman has another well-known villain love interest: Talia al Ghul. Despite being the daughter of notorious terrorist Ra’s al Ghul, Talia has always cared for Batman in her own twisted way. She’s also the mother of Batman’s son, Damian Wayne, the fourth Robin. While Batman cares for both women, Talia’s numerous atrocities and loyalty to her father have fizzled out any chance of him ending up with her. In contrast, Batman and Catwoman will always be DC Comics’ greatest will-they-won’t-they couple.
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