Most people have a stereotypical view of relationships in comic books. Traditionally, a superhero has a girlfriend who gets into trouble (either by getting kidnapped or wandering into it herself) and the hero has to come save her. Obviously, comic book storylines get way more complex than that, but that's considered the classic story. How many times has Superman saved Lois Lane over the decades? All of Sam Raimi's Spider-Man films ended with Mary Jane getting kidnapped and Spider-Man having to save her. That's just typically how most people picture relationships in comics. The superhero has to have a constant significant other so that they always have someone to save.
Of course, that's often not the case. Many superheroes date other superheroes. Others may date regular people, but people who can handle themselves when they get in trouble. Also, comic book writers have grown more mature, and have started to depict more realistic relationships. That means that the "damsel in distress" doesn't always stick around. This being comics, break-ups often don't go well. In fact, they often result in some sort of major tragedy occurring. Real relationships go bad, and these superhero relationships went super bad when things went sour. Here are the messiest superhero break-ups ever!
15 CYCLOPS AND MADELYNE PRYOR
When a break-up ends up causing a demonic invasion in New York City, things have really gone off the rails. After the supposed death of Jean Grey, Cyclops meets Madelyne Pryor in Uncanny X-Men #168 (1983) by Chris Claremont and Paul Smith. The two quickly fell in love, got married and had a son. Then Scott found out that Jean was still alive and abandoned his family.
Understandably, Pryor was upset. With her life falling apart, she ends up making a deal with the demons N'astirh and S'ym. This eventually led to the creation of a bridge between New York City and Limbo, temporarily combining the two realities in Inferno (1989). Fortunately, the X-Men were able to save the city, although Cyclops' reputation would be forever ruined.
14 GREEN LANTERN AND HAWKGIRL
It's never a good idea to keep secrets from a significant other, especially if those secrets involve an alien invasion. The first two seasons of Justice League (2001) depict Green Lantern John Stewart and Shayera Hol, aka Hawkgirl, falling in love. In the second season finale "Starcrossed," Shayera reveals that she's a scout for the Thanagarians, an advanced alien species.
Then it turns out the aliens want to destroy Earth, making Hawkgirl look like a traitor, ending her relationship with Stewart. The League fights off the Thanagarians, and Hawkgirl briefly leaves the team. She eventually returns, which causes problems for Stewart, who still had feelings for her but was dating Vixen. This is why it's never a good idea to date a coworker, or the advanced scout for a hostile alien species.
13 JOKER AND HARLEY QUINN
To be honest, these two never really had what anyone would call a "healthy" relationship. So, it's not shocking that the break-up didn't go well. Harley Quinn first appeared as a character in Batman: The Animated Series (1992). Due to her popularity, she eventually debuted in the comics as the Joker's girlfriend. Of course, being the Joker, their relationship was abusive and awful and incredibly one-sided.
Harley slowly came to realize that she didn't need the Joker. Considering how he treated her, it's also not surprising that she didn't let him off the hook easy. The relationship finally came to its conclusion in Harley Quinn #25 (2016) by Amanda Conner and Jimmy Palmiotti. While breaking someone else out of Arkham, Harley entered the Joker's cell and beat him to a pulp. She then left him in his cell, bleeding and alone.
12 COLOSSUS AND KITTY PRYDE
During Secret Wars (1984) by Jim Shooter and Mike Zeck, Colossus fell in love with an alien girl named Zsaji. He, along with a number of other heroes, had been transported to Battleword to take part in a contest by the Beyonder. The problem, however, was that Colossus was dating Kitty Pryde, who had been left back on Earth. While Zsaji sacrificed her life to save the heroes, Colossus returned to Earth heartbroken and ended things with Kitty.
Wolverine, who was very protective of Kitty, didn't appreciate this. So, he took Colossus to a bar in Uncanny X-Men #183 (1984) by Chris Claremont and John Romita Jr. There, Logan lets the Juggernaut pummel his Russian teammate, who ultimately gets the building dropped on top of him. Wolverine just lets this happen, and then lectures his injured teammate about honor.
11 THE ATOM AND JEAN LORING
The DC universe can't stop having crises. One of the least destructive, but still most memorable of these was Identity Crisis (2004) by Brad Meltzer and Rags Morales. The story kicks off with the murder of Sue Dibny, wife of the Elongated Man. This launches a series of events that reveals dark secrets from the Justice League's past, fractures friendships and results in several more dead bodies.
During the story, the Atom's ex-wife, Jean Loring, is seemingly attacked, although she survives. It turns out, all of the murders were a plan by Loring to win her husband back. Also, all of the deaths were apparently accidents, making this one of the most disastrous plans ever concocted. This story led directly to the events of Infinite Crisis (2005) by Geoff Johns.
10 BRUCE WAYNE AND SELINA KYLE
Batman can never have a simple relationship. In Batman Returns (1992), Bruce Wayne meets and falls for Selina Kyle. At the same time, Batman begins an adversarial relationship with Catwoman. Neither person is aware of the other's dual identity, making it the perfect recipe for disaster. It all falls apart when Bruce and Selina attend a party together, where they both repeat a phrase that they had said to each other in costume.
After some initial discomfort, there's a moment where it seems like they might be willing to overlook their vigilante differences. Unfortunately, the Penguin attacks the party, resulting in a huge showdown at his sewer lair. There, Catwoman chooses murder/suicide over Bruce Wayne, which is probably the most painful way to "let somebody down." At least the two eventually got together in the comics (although it remains to be seen if their marriage will actually happen, let alone whether they will live happily-ever-after).
9 ULTIMATE HANK PYM AND THE WASP
While the mainstream Hank Pym has done some horrible things, it's nothing compared to his Ultimate counterpart. In this alternate universe, Hank Pym was married to Janet Van Dyne, and together they joined S.H.I.E.L.D.'s superhero team in The Ultimates (2002) by Mark Millar and Bryan Hitch. At first, the two seemed to have a healthy relationship. Then, during the Hulk's attack on New York City, Hank is injured.
Embarrassed by his performance, along with Jan's growing friendship with Captain America, Hank flies into a rage. This results in him severely beating Jan, sending her to the hospital. He even used his Ant-Man powers to send a swarm of insects after her. The news shocks the rest of the team, and Captain America responds by tracking Hank down and starting a fight. Cap beats the man, and forces Hank into traction and off the team.
8 DICK GRAYSON AND STARFIRE
He might be most well known as Batman's sidekick, but Dick Grayson has also had just as substantial career as the leader of the Teen Titans. During his time with the team, he began a relationship with fellow Titan, Starfire. An alien from the planet Tamaran, she and Grayson had a rocky, yet relatively steady relationship that almost resulted in them getting married. In fact, the whole wedding was all set to happen until tragedy struck.
Raven, who was evil at the time, crashed the event. This resulted in Starfire getting implanted with a demon seed. This forced her to leave Earth, and Nightwing, behind. Though he still loved her, the distance killed the relationship. Also, it's usually considered bad luck when an evil entity crashes a wedding and starts murdering people. It's a worse omen than the groom seeing the bride before the ceremony.
7 PETER PARKER AND MARY JANE
Nerdy Peter Parker grew up to marry a supermodel. When he tied the knot with Mary Jane Watson in Amazing Spider-Man Annual #21 (1987) by David Michelinie, Jim Shooter and Paul Ryan, the character was fundamentally ruined. At least, that's what some fans (and creators like Joe Quesada) believed. That's not to say that everyone hated the marriage; it's just that the people who hated it truly despised it.
Decades later, the marriage was finally undone in One More Day (2007) by J. Michael Straczynski and Joe Quesada. After Aunt May is mortally wounded, Peter can't find anyone who can cure her. Then, Mephisto shows up and offers Peter a deal to save May in exchange for wiping the marriage out of existence. Mary Jane accepts for Peter, and history is rewritten. If Mary Jane wanted out, getting divorced is always easier than making a deal with the devil.
6 KATE KANE AND RENEE MONTOYA
Kathy Kane originally appeared as Batwoman all the way back in Detective Comics #233 (1956) by Edmond Hamilton and Sheldon Moldoff. In her original appearances, she was meant to serve as a love interest for Batman. While popular, the character disappeared from DC's comics for several decades, and a new version of the character (now named Kate) debuted in 52 #7 (2006).
Kate Kane was a lesbian, and it was revealed that she had been in a relationship with Renee Montoya. The two briefly rekindle their romance later on, but things didn't work out. This was complicated when Renee became The Question, and they're forced to take on a religious cult together. Again, this is why people who work together shouldn't date (even if that work is vigilantism).
5 STORM AND BLACK PANTHER
In Marvel Team-Up #100 (1980) by Chris Claremont and John Byrne, it's revealed that Storm and Black Panther have known each other since childhood. In 2006, Marvel announced that the two would marry, and they quickly became one of Marvel's most prominent and powerful couples. They even went on to briefly lead the Fantastic Four. Of course, this being comics, tragedy soon struck.
In Avengers Vs X-Men #8 (2012) by Brian Bendis and Adam Kubert, a Phoenix-possessed Namor (a member of the X-Men) attacks and destroys Wakanda. As Storm had sided with the X-Men, and Black Panther with the Avengers, this permanently destroyed their relationship. Black Panther announced the marriage annulled as he stood in the ruins of his once beautiful kingdom. Since then, it appears that the two former lovers have completely moved on from each other.
4 CYCLOPS AND JEAN GREY
Making his second appearance on this list, Cyclops proves he's a terrible husband. Granted, he's had a pretty messed up life. For example, he was once merged with Apocalypse and forced to live a hellish existence. Thankfully, Jean Grey and Cable tracked him down and exorcised En Sabah Nur's spirit from his body. The experience traumatized Scott, however, and his relationship with Jean was strained.
During Grant Morrison's run on New X-Men, Scott begins having telepathic therapy sessions with Emma Frost. The sessions quickly turn into a psychic affair, which Jean telepathically walks in on. While Scott insists that nothing physical ever happened, it's not a great excuse. Jean is soon killed by Xorn/Magneto (it's a complicated story that's been retconned several times) before the two can reconcile their relationship.
3 DAREDEVIL AND KAREN PAGE
Some break-ups aren't immediately messy. For example, while it might have broken Matt Murdock's heart when Karen Page left him, it didn't immediately cause any major problems. Those would come later on down the road. Page broke up with Matt after learning his secret identity and realizing that she couldn't handle the stress of his life. She moves to California where she has a briefly successful acting career.
Unfortunately, things didn't work out and Page ended up performing in rather more salacious movies and addicted to illicit street substances. While in this state, she sold Matt Murdock's secret to pay for another hit. The Kingpin eventually got his hands on it, and used it to slowly and systematically destroy Murdock's life. Matt is eventually left broke and homeless, although he eventually rebuilds his life. The events played out in the 1986 Born Again storyline by Frank Miller and David Mazzucchelli.
2 BLACK BOLT AND MEDUSA
As the heads of the Inhuman royal family, Black Bolt and Medusa seemed inseparable. Things fell apart, however, when Black Bolt made a drastic decision to save the Earth from Thanos. During the 2013 Infinity storyline by Jonathan Hickman, Black Bolt changed the world by detonating a bomb and releasing the terrigen mists across Earth. This caused new Inhumans to manifest powers across the globe. Black Bolt then went into hiding, leaving his fate a secret.
During this time period, the Inhumans were forced to deal with a rising population and growing tensions with the mutants. Medusa eventually had Black Bolt tracked down and returned home, but only so that she could officially banish him from the throne. The two would eventually reunite, but only after spending years (and several bloody conflicts) apart.
1 SPIDER-MAN AND THE SYMBIOTE
This might not seem like a typical break-up, but whatever passes for a symbiote's heart was broken when Peter rejected it. Spider-Man first encountered the alien in Secret Wars #8 (1984) by Jim Shooter and Mike Zeck. At the time, he didn't realize that it was a living thing, and thought that he was just wearing a fancy costume.
In short order, Peter found out that it was a living thing, and that it had become very attached to him. With the help of the Fantastic Four, Peter freed himself and thought he was done with it. He has never been more wrong. The symbiote eventually escaped from Reed Richards' lab, and bonded with Eddie Brock. This created Venom, who's fueled by his hatred for Spider-Man (although, the symbiote has shown that it would take Peter back if he would let it).