Oh, Deadpool. It's as if someone gave sentient form to the very concept of bad choices. As much as we might find entertainment in good old Wade Wilson, even the most diehard Deadpool stan has to admit that the guy's kind of a mess even in the best of times.
It probably shouldn't surprise anyone, but Deadpool's relationship history is a bit rocky. Although he appears to have good intentions, he sure does have a whole lot of ex-wives, and an inordinate amount of former partners that either want him dead or are dead themselves. In one very special case, they're back from the dead; in another, his lover is actual, literal Death.
I'm just saying: maybe don't date Deadpool.
Copycat (Vanessa Carlyle)
This entry is pretty depressing, so buckle up, it's going to be a bumpy night. Out of all of Deadpool's exes, Vanessa Carlyle was probably the one that was the most into him, although that manifested in an incredibly unhealthy obsession and ended in, well... her death.
Vanessa and Wade were in love up until he became physically deformed via the Weapon X program's experiments on him, at which time he left her rather than force her to deal with his appearance. Vanessa became a mercenary in her own right, and when she found out Deadpool was still alive they began their relationship anew, only for her to be crushed when she discovered he was falling for someone else. Taking his form and attacking his then-current love interest Siryn, Copycat set out to inflict as much harm on Wade as he had to her. In the end, she was killed by Sabretooth, slowly dying in Wade's arms. Despite the fact that no one stays dead in comics and she eventually came back, Vanessa has always been unstable, demonstrating an obsession with Wade that brought her nothing but suffering. Also, one time, she dated a guy that could shoot metal hands from his wrists. That's not really related to this, I just needed a pick-me-up after this incredibly bleak entry. Metal hand guy. He was pretty cool.
The film version of Deadpool treats Vanessa a little better. Although the story begins much the same, with him leaving her upon his transformation into Deadpool, he does eventually save her life, and the two of them reconcile. Slated to appear in Deadpool 2, only time will tell what the cinematic universe's overall take on Copycat will be, but we hope it's a little kinder to her than the comics have been.
Poor Satana, Daughter of Satan. First of all, her brother is Damien Hellstrom and he is kind of a chump. Damien's claim to fame was being briefly married to Patsy Walker aka Hellcat, but he basically drove her to madness before she finally left him. You might think that might not have much to do with Satana, but pay attention — bad relationship choices run in their family.
Secondly, her dad isn't even Satan, which is a huge rip-off. Can you imagine going to school and telling all the kids your dad is actual Satan, only to discover there's like 30+ Satans in the Marvel Universe and literally none of them are your dad? Her dad is just some random demon who showed up, and nobody even asked to see his ID so everyone just believed him and named her after him only to discover, years later, nope. Nary a Satan to be found in this tale, I'm afraid.
So, we're off to a bad start, but don't worry: it gets worse. After losing a bet with some nerds, she found herself betrothed to one and hired Deadpool to murder him. This would normally be a pretty standard open-and-murder case, but it turned out the nerds in question were actually demons, therefore somewhat more difficult to kill than your ordinary dweeb. Deadpool, being the genius he is, offered to simply marry her so she wouldn't be obligated to marry anyone. She took him up on it, and the two lived happily ever after.
Just kidding! Satana not only divorced him but jacked half of his soul. How one even divides a soul into halves is only one of many questions that have yet to be answered, but rest assured, Satana lived to marry randos, hire hitmen, and steal souls another day.
Mercedes was once the wife of Wade Wilson. Or she wasn't. Who knows? Who goes around in life remembering all the people they've married? Definitely not Mercedes, who actually didn't recall most of her life.
Widely known as one of the more confusing stories to be told in a comic universe full of confusing stories, the backstory of Mercedes was given to us via T-Ray, who was Deadpool's arch nemesis for a hot minute before we all got kind of sick of him and he bowed out of the spotlight after 30 issues or so. T-Ray spun a ridiculously over-the-top complicated tale in which he himself was the real Wade Wilson and Deadpool was just some guy that stole his identity after accidentally murdering his wife, Mercedes. Okay, sure. Anyway, the real Deadpool beat up T-Ray, but Mercedes had already begun telling Deadpool to stay away from her (because she is the smartest person to ever appear in a comic book).
The closest thing to a happy ending Mercedes could get is a life without Deadpool mucking around in it. He might have meant well, but from beginning to end he caused her nothing but problems. Since she was characterized primarily within Wade's arc, we're unlikely to see her again anytime in the immediate future. This is one of those characters that was more or less created just to be tormented and then written out of the book.
Theresa Rourke is a rare specimen in that she has about as many problems as Deadpool does. With a backstory that combines pretty much every Irish stereotype known to humanity into one single character, this poor girl was doomed from the start to a difficult life among the X-Men. Her father is the X-Men's Banshee, but she was raised by his brother, the villain Black Tom Cassidy. Sometimes he had her pull crimes for him — it was a mess. She had a short stint on Muir Isle with a few other fairly nondescript mutant guest-stars, eventually joining Cable's X-Force.
At the time of her relationship with Deadpool, Siryn was simultaneously dealing with standard “nice guy” behavior from James Proudstar, otherwise known as Warpath. Their love was not to succeed, as Teresa repeatedly blew James off and he stood around looking sad about it and taking it way too personally (no shade, we've all been there). Meanwhile, Deadpool was upping his ante when it came to flirting, and she made kind of a messed-up move by leading him on and saying he might have a shot if he got his sh*t together. Reader, he did not have a shot, and it caused him a lot of pain when he realized that to be the case. Let that be a lesson: conditional love is no love at all.
The villain Typhoid Mary seduced Wade while masquerading as Siryn, causing him to fly into a downward spiral when he realized she'd done so. Apparently, Mary did the whole thing on a whim; women are usually inexplicably evil in Deadpool stories, because you've got to stretch pretty far to make him seem like he's the one being victimized. Siryn and Deadpool went their separate ways, although she did eventually sleep with him after the loss of her child if only to reduce the pain she felt. These two... are not a great match.
Okay, hear me out. Deadpool has been hinted as being pansexual for some time by many, even by his creator, Fabian Nicieza, who claims to be practically hounded by questions on the subject. Deadpool's “equal opportunity” flirting could be interpreted as part of his bit, but it shouldn't be so hard to believe that he's pansexual when so many people that have worked on his films and comics have agreed with the assessment—and when he's been consistent in flirting with everyone from Thor to, you know, the living embodiment of death (we're almost there).
In Cable & Deadpool #20, a kidnapped Deadpool is held and tortured by a group of female villains led by Diamondback. Via a dream sequence, said to be one of his darkest fantasies, we see Wade on a beach with Cable, giving him a backrub. This leads to Deadpool trying (in vain) to prove his masculinity to women, but the damage has been done, and everyone knows about his secret crush on Cable. It's not exactly a full-fledged ship, but the seeds have been planted, and, honestly, a polyamorous love affair between Cable, Domino, and Deadpool could be a beautiful thing. It makes as much sense as anything else on this list!
While Deadpool has flirted with other heroes such as Thor and Spider-Man, neither of them gave him the time of day. Meanwhile, Cable admits to having strange dreams about Deadpool too, leaving me to wonder what could have been and what might yet be.
In the Marvel Universe, Death is the kind of lady that likes to keep her options open. Despite being pursued by renowned dork Thanos ad nauseum for about a billion years or so, she also dated Deadpool for a while—if “dated” means “showed up when he was on his deathbed suffering from delirium tremors and made out with him a bunch." I don't know what kind of life you're leading, but I consider that to be quite the successful Tinder date.
Of course Thanos was very angry, because he loves getting mad about every little thing, so he cursed Deadpool to endless life just so he wouldn't be able to die, thereby preventing him from making out with Death. Thanos is SO. CONTROLLING. Anyway, Thanos and Wade had to team up for the Thanos vs. Deadpool miniseries in which Deadpool torments Thanos about their shared love for Death, flirts with Thanos a bit, and ends up ditching them both when he discovers that he is chaotic like life, not goth like Death. The power was inside him all along. Thanos and Death go on to have a really weird chaos demon baby thing together, while Deadpool goes on to do more Deadpool stuff. Long story short? Deadpool actually broke up with Death.