For a guy who is supposedly notoriously hard to look at, Wade Wilson seems to have quite a way with the ladies.
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The most recent example of this was in Uncanny Avengers, where even after Deadpool did his best to warn her away, Rogue still made out with the mercenary turned Avenger, a moment long in the making as the two have grown closer and closer together during the time on the Avengers Unity Squad.
Even the Deadpool movie was in large part a love story, telling of how Wade and Vanessa’s great love fell apart only for them to finally be reunited in the end.
But Deadpool has had plenty of other romantic leading ladies in his life. With the latest moment in Uncanny Avengers and casting for Deadpool 2 picking up, ComicBook.com felt now was as good of a time as any to look back at Deadpool’s five best love interests.
Keep reading to see our pick’s for Deadpool five greatest loves.
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5. Siryn
Deadpool’s relationship with Theresa Cassidy, the mutant daughter of Banshee, was never a particularly happy one. They met on a mission to defeat Black Tom Cassidy and the Juggernaut. Deadpool’s mask came off and Theresa reflexively gasped. Deadpool closed up after that, but Siryn coaxed him back into being himself with a touch.
Deadpool became a bit obsessed with Siryn after that, even watching her while she slept. Siryn later admitted she knew Deadpool was there and said it made her feel safe, but that doesn’t really make it any less creepy.
Siryn and Deadpool’s relationship hit a major obstacle when Typhoid Mary disguised herself as Siryn and had sex with Deadpool. Later, Siryn tried to reconcile with Deadpool, but his shapeshifting ex-girlfriend Copycat took Deadpool’s form and assaulted Siryn.
Later, after going through a dark period following the death of Banshee and the death of her child, Siryn had a final one night stand with Deadpool and then proclaimed their relationship through.
4. Outlaw
Outlaw, Inez Temple, is a mutant with extremely enhanced who also works as a mercenary. Deadpool met Outlaw at the gym during a time when he was the top of the mercenary game, but the two didn’t do much other than flirt.
Deadpool went missing for a while and Outlaw fell in love with a Deadpool lookalike named Alex Hayden, a.k.a. Agent X.
When Deadpool returned, he started teaming up with Outlaw and Agent X, who had formed Agency X. Deadpool flirted a lot, even shared a couple of games of strip poker, but the two did actually get together until after Deadpool spent a small fortune replacing Outlaw’s home, which was destroyed during a mission.
Outlaw and Deadpool eventually got married, but even Deadpool’s healing factor wasn’t enough for him to be able to handle a honeymoon activities with a bride with super strength. The marriage was annulled soon after.
3. Copycat
Copycat is the shapeshifting mutant Vanessa Carlyle, who inspired the Vanessa played by Morena Baccarin in the Deadpool movie. She and Deadpool’s relationship begins very much like it did in the film, but ends much more tragically.
Wade Wilson lived with Copycat before he was Deadpool when they were both mercenaries. When Wade got cancer, he left Copycat and went into Weapon X, where they turned him into Deadpool.
Since Deadpool continued to work as a mercenary, it was only a matter of time until he crossed paths with Copycat. That reunion occurred during a time in Deadpool’s life when he was completely amoral, and so he treated Copycat with near total disregard and tried to kill her.
Copycat then entered a relationship with Garrison Kane, another Weapon X alum. However, when Copycat was mortally wounded, Deadpool allowed her to use her power-copying ability to borrow his healing factor and save herself.
Deadpool and Copycat had an on-again, off again relationship from then on, sometimes trying to love each other and sometimes trying to kill each other. Copycat died after Sabretooth gutted her with his claws, telling Deadpool that she always loved him as she died in his arms.
2. Shiklah
Deadpool was hired by Dracula to retrieve a coffin contained the demon succubus known as Shiklah. Dracula and Shiklah were to have an arranged marriage that would unite the monster kingdoms.
However, things went differently when Shiklah broke out. Deadpool agreed to help her and got married along the way just to mess with Dracula.
Later, Deadpool and Shiklah had a real marriage with Deadpool’s friends in attendance. They’ve been married ever since, but the relationship has been stressed ever since Deadpool joined the Avengers and started trying to be a hero. All of that tension in the marriage came to a head in the recent “Till Death Do Us” crossover story, in which Shiklah leads the denizens of the Monster Metropolis to war with the humans of New York City.
1. Death
As if stealing the bride of Dracula wasn’t bold enough, Deadpool has also literally courted Death, who in the Marvel Universe is the object of the affections, wanted or otherwise, of Thanos, the Mad Titan.
Deadpool spent so much time being tortured to near-death in Weapon X that was actually able to see and get to know Death herself. The two grew to love each other, but the relationship couldn’t last.
In a fit of revenge, Deadpool broke out of Weapon X. Since then, he was only able to see Death during extremely rare occasions when Deadpool was beaten near to dying. But even that came to an end when a jealous Thanos cursed Deadpool with eternal life.
A more recent story involving Deadpool and Thanos saw Thanos lift Deadpool’s curse, but also have a falling out with Death, ending what relationship they still had.
