Their adventures might be fun for us to watch, but being a superhero is tough. It involves a lot of long, lonely nights, thankless hours, and wear and tear on the body as they propel themselves across rooftops and take countless punches to the jaw. As if that wasn’t enough, many superheroes also try to maintain a secret identity, which makes their love life into a total mess. Just ask Peter Parker, better known as the friendly neighborhood Spider-Man, about how much it sucks to have to constantly ditch dates every time a fire truck goes by.

Really, it’s no big surprise that many superheroes have romanced fellow superheroes. That approach has worked out pretty well for two of the Defenders, Luke Cage and Jessica Jones. Over on the DC side of things, Wonder Woman and Superman were also lovers for a while there.

But sometimes, even the nicest and most moral superheroes can’t help but be tempted by the allure of the dark side, and this has led to a surprising number of romantic encounters between superheroes and the very enemies that they usually trade punches with. Predictably, these romances don’t tend to end well — when your lover is robbing banks, and you’re trying to stop bank robbers, it gets complicated — but here are 15 superheroes who gave it a go anyway.

15. Batman and Catwoman

Well c’mon, of course we have to start with the obvious one. Batman and Catwoman wrote the blueprint on superhero/supervillain relationships, and how to make them work. They’ve been going at it for decades, and in addition to their crackling chemistry, they also understand one another like no one else ever could: both are vigilantes that prowl Gotham’s rooftops at night, torn between their two halves. Not to mention, they both seem to enjoy engaging in kinky rooftop sex while still in costume.

But seriously, there’s a reason these two click so well. Catwoman is more of an antihero than a proper villain, which helps, and she’s often one of Batman’s closest allies. This relationship might easily be the most successful on this list, considering that the cinematic Bruce and Selina ran away together at the end of The Dark Knight Rises, and in the comics, Bruce legitimately just proposed to her.

14. Rogue and Magneto

Rogue of the X-Men has had a painful romantic history, due to the fact that her powers can cause any person she kisses to slip into a coma (or die) within moments, which makes dating rather complicated. Everyone knows about her strained love affair with the X-Men’s cajun rebel, Gambit, but Remy’s not the only man in her life: she also has a history with the X-Men’s greatest enemy, Magneto.

The surprising May-December pairing between this X-Woman and the self-proclaimed Master of Magnetism first occurred in an alternate reality storyline called Age of Apocalypse, but it later drifted over into the mainstream Marvel Universe as well. It got so far that Rogue at one point became torn between her feelings for Remy and for Magneto –and chose Erik. Later, she actually entered into a serious relationship with the villainous mutant, though it didn’t last.

13. Hulk and Umar

Umar is an unbelievably powerful sorceress, a Faltine, and the sister of Dormammu — yes, that enormous energy being that was the big bad behind last year’s Doctor Strange. This makes her an insanely deadly supervillain, one whom very few heroes could hope to stand up against for more than three seconds. Naturally, this means that it would make sense to send a being of similarly unstoppable power — such as the incredible Hulk — to stop her. But when Umar encounters the green-skinned behemoth, rather than trade blows, she lets her libido do the talking.

Hulk resists for a minute, throwing out one of his customary “Hulk smash!” proclamations, before giving in. Umar, for her part, finds the whole experience somewhat unsatisfactory, and makes an annoyed statement about wishing the Hulk had lasted longer.

12. Spider-Man and the Black Cat

Mary Jane might be the woman who Spider-Man finally got married to, and Gwen Stacy might have been his first love, but he had plenty of other tangled up, messy, and confusing romances along the way. One of the most notable, and most exciting, was with a woman named Felicia Hardy, a cat burglar who likes hopping on rooftops as her alter ego, the Black Cat.

Sparks flew as soon as she and Spidey entered each other’s sight. Felicia soon turned her career around and became a hero; her heart wasn’t really in the villain business. Spider-Man and the Black Cat became vigilante partners, and soon, romantic partners as well — but rather unfortunately, their relationship floundered when Felicia found herself less attracted to the nerdy, average Peter Parker than she was to the edgy, quipping Spider-Man. The two eventually parted ways. Black Cat, for her part, will possibly be making her cinematic debut next year sans Spidey, in a movie titled Silver and Black.

11. She-Hulk and Juggernaut

We should stipulate that at the time this story occurred, Juggernaut was actually a reformed villain: he’d hung up his villain hat, changed his ways, and joined up with the X-Men. It wasn’t until much later that he became a villain again. Furthermore, later retcons have clarified that the She-Hulk in this story was actually her counterpart from an alternate universe, and the real Jennifer Walters was in disbelief about the whole thing, since she had no memory of any such event occurring for some years.

Either way, this wasn’t anything particularly romantic: She-Hulk and Juggernaut’s onetime tryst was entirely about two invulnerable beings with super strength taking advantage of an opportunity to not hold back, and judging by the image above, the whole thing was a casual encounter that was definitely enjoyed by both parties.

10. Batman and Talia al Ghul

So yeah, when it comes to superheroes getting romantically entangled with their villains, Batman is definitely the biggest repeat offender out there, and we’ll be seeing him again on this list. While Catwoman is probably Bruce Wayne’s most famous love interest, second place goes to a woman whose relationship with him is even more complicated.

See, the problem is that Talia is the daughter of one of Batman’s greatest enemies, the eco-terrorist known as Ra’s al Ghul. Furthermore, Talia is highly loyal to her father’s cause. Seeing as Batman can’t possibly support horrific acts like genocide or mass murder, a successful relationship with Talia is probably out of the question. Nonetheless, the two did actually have a child together: Damian Wayne, who has since become Robin. However, the situations regarding Damian’s birth and upbringing are pretty murky, to say the least.

9. Wolverine and Mystique

Who doesn’t remember that scene in X2: X-Men United where the shape changer known as Mystique slips into Logan’s tent, then attempts to seduce him? In that instance, Wolverine rejected her advances, but in the comics, they’ve been together a few times.

The two actually met all the way back in 1921, when the two joined up with the same gang. They quickly became lovers, but the relationship ended badly, with Raven pushing Logan out of a train. Since then, their relationship has mostly been contentious, with both of them tending to be on opposite teams in the mutant conflict, and Mystique often sharing a bed with Logan’s hated enemy, Victor Creed. However, there is at least one possible future where they have a son together, named Raze Darkholme, who possesses the same powers as both of his parents, including shape-shifting blue skin and claws.

8. Green Lantern and Star Sapphire

As the Vice President of Ferris Aircraft, Carol Ferris actually hired cocky test pilot Hal Jordan as an employee, but soon became attracted to him. The two began a relationship soon afterward, though it got complicated by two factors. First, when Jordan himself was given an emerald power ring by the dying alien Abin Sur, and then inducted into the Green Lantern Corps, and second, when Carol Ferris found herself chosen by an immortal race of warriors known as the Zamarons to be their queen, the Star Sapphire. The Zamarons weren’t too happy to find out that Ferris was in love with a Green Lantern, so they pitted the two against each other in combat. The two lovers have battled many times after that.

Later on, Star Sapphire and the Zamarons formed the Violet Lantern Corps, or the “Star Sapphires,” who wield rings fueled by the power of love. In recent years, Star Sapphire has usually been depicted in a more heroic light.

7. Cyclops and Dark Phoenix

Cyclops has become a controversial figure in recent years, with many arguing that he’s actually more of a villain now than he is a hero. However, back during the original Dark Phoenix storyline, he was one of the central protagonists of the X-Men. In all fairness, when he fell in love with Jean Grey, she was a fellow X-Men teammate. The whole thing where she became a nearly omnipotent evil figure capable of destroying galaxies, well… that happened later, and he stayed loyal throughout it.

However, Dark Phoenix wasn’t the only supervillain whom Cyclops has gotten involved with. He also had a romance with Madelyne Pryor, a clone of Jean Grey designed by Sinister. When Scott left Madelyne, she went on to become the villainous Goblin Queen. So that’s at least two women who became villains only after being with Cyclops…

On the other hand, his relationship with Emma Frost went a lot better than either of those two, so that’s something.

6. Supergirl and Lex Luthor

So, yeah, this happened. It’s a complicated story that gets all tied up in universe reboots, retcons, and so on, but we’ll try to streamline it. Basically, the Post-Crisis version of Supergirl was a synthetic being named “Matrix” that came from another dimension, a so-called “pocket universe,” where she was actually created by a not-so-evil Lex Luthor.

When she came to the regular DC Universe, she fell in love with the young, red-haired “Lex Luthor Jr.,” who was supposedly Lex’s son. This Lex was later revealed to be the real Lex, who had transferred his consciousness into this younger body after his original body got cancer from kryptonite poisoning. Supergirl and Lex were together for some time, until she discovered that Lex was making clones of her, at which point she ended the relationship and wrecked his lab.

5. Iron Man and Madame Masque

The Whitney Frost that appeared on Agent Carter is a loose adaptation of the comic book character Madame Masque, an antagonist and love interest for Iron Man. The comic book Whitney is a famous celebrity, but secretly the daughter of the evil Count Nefaria, who wants her to become the leader of the Maggia, the Marvel Comics version of the Mafia. After her face is badly disfigured in a plane crash, she begins wearing a metal face mask and referring to herself as Madame Masque.

She meets Tony Stark after this point, and is blown away by the billionaire’s ability to care for her despite her heavily scarred appearance. When they learn one another’s true identities, Stark and Frost begin dating, though the relationship fails due to the conflict between Whitney’s criminal enterprises and Stark’s superheroic career as Iron Man.

4. Ant-Man and the Beetle

Yep, that’s right. Two bugs in the bed, or “bedbugs,” and it just so happens that the two of them work on opposite sides of the law. This is exactly the sort of event that would happen to Scott Lang.

Janice Lincoln is the Beetle, a tech-powered supervillain who uses flight armor and wings to pull off her crimes. The event above occurs during one lonely and painful night, where Ant-Man figures he’ll work out his sadness with alcohol, and heads to the nearest bar. While there, he spots an un-costumed Beetle in the distance, and decides he’s going to bring her in for her attempted murder of Tony Stark. This doesn’t go as planned, when Janice suggests that they do something else instead.

The next morning, they wake up in the same bed, in Janice’s apartment. Somehow, Scott’s still wearing his helmet.

3. Sue Storm and Doctor Doom

Victor Von Doom is a fantastically complex character. Charismatic, noble, and loyal, yet also scheming, jealous, and petty, Doom is easily one of the most fascinating characters in comics. His biggest weakness has always been his pride, which feeds right into his resentment of Reed Richards, the only man on the planet who is (infuriatingly) smarter than Doom is. Perhaps, then, it’s no surprise that Doom covets the one thing that Richards holds the most dear: his wife, Sue Storm, the Invisible Woman.

In the storyline Secret Wars, Doom takes on all of the reality-molding powers of the Beyonders, and reshapes the multiverse according to what he desires. This results in a new universe, Battleworld, wherein he is God — God Emperor Doom, to be precise. But notably, he also crafts the universe such that Sue Storm is now his wife, and she and Reed’s children are now his children. Despite all of Doom’s grandeur, acts like this show the vain jealousy that lurks behind that fearsome metal mask.

2. Daredevil and Elektra

Arguably the most interesting relationship in all of superhero comics is the one shared by the Catholic lawyer vigilante Daredevil and the Greek homicidal assassin Elektra Natchios, a tragedy of classic proportions that has now, finally, been properly adapted in the Netflix series.

What makes this romance so fascinating are the many layers that it has. Matt Murdock is a man torn by the dark conflict within him, and while Karen Page (at least, in her earlier, pre-Born Again appearances) may be the sort of person he thinks he should be with, Elektra is the one he actually wants: edgy, dark, violent, and with a true understanding of the darkness that lies within Matt as well. Unlike Batman and Catwoman’s romance, which is made somewhat easier by the fact that Catwoman tends to be more of an antihero, Matt and Elektra’s saga has no easy outs attached: Matt despises killing, and Elektra loves it.

1. Batman and the Joker

We’re not talking about the regular Batman and Joker; yeah, that Joker’s madly in love with Batman, but Bruce doesn’t seem to share his affection. No, what we’re discussing here is the version of these characters depicted in the Flashpoint universe — an alternate reality wherein a little kid named Bruce Wayne gets gunned down by Joe Chill, instead of his parents.

Watching their son die before their eyes irreparably damages Martha and Thomas Wayne. It results in Thomas becoming a dark figure of the night, the Batman… while Martha snaps, slices her cheeks open in a Glasgow smile, and becomes the Joker. Just as in the DC Universe, the two are archenemies, but the added twist makes things even more tragic.

Anyway, when the Thomas Wayne version of Batman discovers the Barry Allen of the regular universe, the two heroes attempt to rewrite history, to make it go back to what it was before. Thomas tells Martha about this, and the two reconcile… until Martha learns that in the new universe, her beloved son becomes Batman, the figure she hates the most. In response, Martha jumps off a cliff. Heartwarming happy endings all around.

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What other superhero/supervillain pairings did we miss? Let us know in the comments!