In the first Deadpool movie, one of the jokes in the marketing portrayed it as a love story to tie in with the fact that it came out just before Valentine’s Day. It’s not exactly lying as Wade’s actions are all motivated by love.
Sure, he may look like a sculpture made of dried bubble gum and he has some serious personality problems, but Wade Wilson has a lengthy list of love interests over the years. The sense of humor and abs probably help. He’s been married a handful of times. The guy gets around. Let’s take a look at the ladies of his life who could look past his skin texture.
Don’t let that blue-skinned appearance fool you. That’s the same Vanessa that Morena Baccarin plays in the movies.
Copycat lived with Wade years ago, when he was a simple mercenary. The two would likely have been married and spent the rest of their lives together, but then Wade came down with a bad case of cancer, told Vanessa to hit the road, moved on to Weapon X and things got complicated. Since Vanessa was a mutant shapeshifter, the two ended up working together after Wade became Deadpool. Around this time, Deadpool was complete human garbage and not only treated her badly, but at one point tried to kill her. Copycat left him for Garrison Kane, a character who isn’t allowed to appear outside of the 1990s without first informing his parole officer.
It was under this scenario that Deadpool enacted his first in-comic heroic action when he saved Copycat’s life. Her powers were a mix between Mystique’s shapeshifting and Rogue’s power copying, so when she was mortally wounded, Deadpool tore off the top of his uniform and hugged her so that she’d copy his powers and heal herself.
When Deadpool became more of a good guy, Copycat targeted him and failed. Then she tried to get back with him through disguising herself as various women interested in dating him. Deadpool later admitted that he knew it was her and the two rekindled their relationship.
Copycat became aware of Deadpool’s friendship with Siryn, became jealous and left him. Another reason why she left came from issues with her powers. She started working with a reformed Weapon X and they enhanced her abilities, but there were some serious side-effects. Weapon X brought Deadpool back into the loop and gave him the mission of killing Copycat. Deadpool instead rebelled and tried to save her life. She was sliced to ribbons by Sabretooth and died in Deadpool’s arms, swearing that she always loved him.
Every writer practically forgot about this afterwards, as Deadpool had crossed paths with Sabretooth on occasion and never had the sensible, violent reaction. It wasn’t until AFTER the movie was released when Deadpool even brought that up. Even then, it was a secondary reason for him to consider killing Sabretooth.
Due to a history between Banshee and Deadpool, Siryn ended up working alongside Wade during an adventure where they battled Juggernaut and Black Tom. During a fight with Juggernaut, Deadpool’s mask came off and he begged Siryn not to look. Her gasp at seeing his face broke him down, but then she coaxed him with her touch and apologized. From there, Deadpool became infatuated with her and would regularly watch over her when she was asleep.
She later admitted knowing he was there and feeling safe about it. Still creepy!
Siryn acted as the angel on Deadpool’s shoulder for a while, trying to steer him in the right direction. Unfortunately, Deadpool had a devil in Typhoid Mary, who disguised herself as Siryn and had sex with him, which caused him to have a major emotional breakdown. Once things with her team, X-Factor, settled down, she tried to get back with Deadpool, only for Copycat to take Deadpool’s form and beat her up, causing her to despise him. She forgave him at some point, although the passion was gone.
When dealing with a ton of depression due to the deaths of her father and her baby, Siryn had a one night stand with Deadpool. She seemed to regret it immediately and told him that it was over between them the morning after.
Ah, the classic star-crossed lover story. The man who can’t die and the woman who is literally the embodiment of dying.
When being experimented on in Weapon X, Wade was so close to dying most of the time that he was able to see Death looming over him. Wade found himself in love with the skull-faced entity and she grew to love him too, what with him carrying the stench of murder.
As torturous as his days in Weapon X were, it was his time with Death that made it bearable. He planned to goad super-powered orderly and all-around jerk the Attending into killing him (mainly by calling him his real name of Francis), but Attending took out his frustrations on Worm, a fellow experiment who idolized Wade and even gave him the name Deadpool. Attending removed Deadpool’s heart, which should have killed him, but as much as he wanted to spend his eternity with Death, Deadpool found his body healing for the sake of carrying out revenge in the name of Worm.
Once that business was done with, Deadpool couldn’t hear nor see Death anymore. Occasionally, he’d reach a state of near-death good enough to be able to meet with her until he was actually killed. Before the two could touch, Deadpool was revived on Earth. Turned out a jealous Thanos had used a cosmic artifact to give Deadpool eternal life.
A more recent adventure between Deadpool and Thanos ended with not only the end to Deadpool’s immortality curse, but he had a falling out with Death and moved on.
A major climactic moment happened in Deadpool’s solo series where a cosmic being that spreads pure bliss came to Earth and turned everyone into drooling, happy vegetables. Deadpool chose free will and killed the creature. The whole incident caused some repressed memories to return and he started to see visions of a specific woman wherever he went. He ended up finding this woman, who he began to remember as his wife Mercedes, and the two were equally confused. Especially when it was established by supervillain the Black Talon that Mercedes had died and was mysteriously brought back to life.
Deadpool told the story of how he and Mercedes were happy together until evil mercenary T-Ray showed up at their home, half-dead. They took him in and in return, T-Ray killed Mercedes. Deadpool and Mercedes tried to run off to live happily ever after, but T-Ray caught up with them and revealed the truth: T-Ray was the real Wade Wilson and Mercedes was his wife. The two of them took in a mercenary named Jack who proceeded to kill Wade in an attempt to steal his life and accidentally took out Mercedes too. Then he believed himself to really be Wade Wilson and we got another big piece of Deadpool’s origin.
This was meant to break Deadpool, but despite being shown the possibly thousands of people he’s killed over the years, the only victim he ever truly felt guilty about was Mercedes. Then he pointed out that he’s at least trying to be better while T-Ray resurrected his dead wife for no reason other than revenge. Mercedes turned on T-Ray, but made Deadpool aware that she never wanted anything to do with him ever again.
In a story that seemed more Punisher than Deadpool, our hero was hired by some police officers to assassinate a handful of mobsters. Deadpool agreed because he needed the money and killing a bunch of bad people isn’t the worst thing he could do to earn it. His contact was Anastasia, an attractive tattoo artist that Deadpool fell for immediately, partially for her dark sense of humor. On his third visit, she said that she really needed to give him a tattoo or else people would get suspicious, which led to Deadpool having to unmask in front of her. To his surprise, she seemed rather into his grotesque features.
Deadpool would continue his job and would regularly come back to spend time with Anna. Fearing for her safety, he gave her a bunch of money and a phone, telling her to leave town until the whole thing blew over. Then it turned out to be one of those situations where everybody involved was corrupt and stabbing each other in the back.
Anna turned on Deadpool and knocked him out with a shovel to the head. She buried him alive, but dug him up when her situation went south and she needed any help she could get. Once things were done with, Deadpool refused to trust her, feeling used from the beginning. Anna swore that that wasn’t the case and handed Deadpool a gun. If Deadpool truly felt that way, he’d shoot her dead, but she was confident that he wouldn’t.
Deadpool shot her dead.
He felt guilty about it for a while and was surprised when it turned out she was still alive. He married her in Vegas, but she was gone the morning after. What Deadpool never did realize was that Anna actually was dead. This was just Copycat messing with him.
“Crazy” Inez Temple
After pulling off a spectacularly impossible mob hit, Deadpool became the top name in mercenary killings and the envy of everyone in his line of work. While at the gym, he met fellow mercenary Outlaw, a cowgirl with the mutant power of enhanced strength. The two flirted and even crossed paths before one of his missions later on, but nothing of note happened. Mainly because Deadpool fell off the radar soon after and was believed to be dead.
Outlaw fell in love with Alex Hayden, otherwise known as Agent X. Due to his healing factor, personality, scarred features, competency as a killer, and the fact that he showed up shortly after Deadpool went missing, many believed him to be Deadpool with amnesia. Their relationship came to an end when Alex cheated on her with his secretary Sandi (which was more of an instance of fill-in writer Evan Dorkin not quite getting the characters), but she at least stayed close to him as a member of his new organization Agency X. Around this time, Deadpool came back into play and he found himself teaming up with Agency X multiple times.
At first, Deadpool’s relationship with Outlaw never got much further than flirting and the occasional game of strip poker. During the story Suicide Kings, Deadpool was on the run due to belief that he caused a terrorist explosion. He hit on her a bit, but she swore that she had a boyfriend as a way to shut him up. Trouble followed, destroying Outlaw’s apartment and causing her to be very cross with Deadpool.
Once the adventure was done with, Deadpool spent a lot of money on getting Outlaw a new place to live. Since she could tell that Wade did this out of the goodness of his heart and not for the sake of getting into her pants, she rewarded him by letting him get into her pants.
The two got married at some point, despite Alex’s warnings. The honeymoon was far too much for Deadpool to handle, considering Outlaw’s sexual eagerness mixed with her super strength. His body simply couldn’t heal itself back together fast enough and his pelvis ended up in a thousand pieces over and over. The marriage soon got annulled.
In other continuities, Outlaw has been the go-to love interest for Deadpool. In Deadpool MAX, she was a sex-starved psychopath meant to mix Outlaw, Domino, and Copycat into the same entity and was obsessed with Deadpool to the point of carrying a baby doll with her and insisting that it was his. In Deadpool Pulp, she played the femme fatale who acted as Wade’s old flame on the other side of right and wrong. In the end, he had to kill her to save the US from a massive nuclear explosion.
Not much is really known about Gretchen. Years back, there was a miniseries called Identity Disc that was very blatantly the Usual Suspects starring a group of supervillains and had “Identity” in the title to cash in on DC Comics’ big event comic Identity Crisis. The Kaiser Soze stand-in had a specific reason for each bad guy to do his dirty work, whether it was a way to help them or strictly blackmail. When killing time with Bullseye, Deadpool explained that his reward would be information on where to find his first wife Gretchen, who has a restraining order on him.
He never did get his payoff due to the shocking reveal that the Vulture was behind everything (with the added shocker that he really wasn’t). The story wasn’t very good. Deadpool was last shown sadly looking over a photo of this woman we’ve never heard of before or after this storyline. I’m sure she was very nice.
Early in Daniel Way’s Deadpool run, the Merc with a Mouth ran afoul of Norman Osborn and became a thorn in the Goblin’s side. The newest Thunderbolts team was sent to go deal with him, also very fresh into Andy Diggle’s run on that series. Deadpool had a comparatively easy time dealing with the Thunderbolts except for team leader, Black Widow Yelena Belova. She was able to hold her own and between her fighting skills and looks, so Deadpool ended up going dopey and asked if she had a boyfriend.
At first, Yelena rolled her eyes at his advances, but soon found herself laughing at his one-liners. Yelena was frustrated and amused by his antics, including how he flew a plane towing a banner with his phone number on it. During a fight between the two, Deadpool grabbed her close and kissed her. Black Widow was shocked by this and asked why he’d do that. From Deadpool’s fevered point of view, he saw her as Death and told her he loved her.
Deadpool was decapitated during the story and Yelena helped him by sticking his head back onto his shoulders and letting his healing factor do the rest. Down the line, unbeknownst to Deadpool, we found out that it was never Yelena in the first place, but the more heroic Black Widow Natasha Romanova trying to take down Osborn from the inside. Deadpool and Natasha did cross paths at another time, where he got some mixed signals and received a punch to the face for his troubles.
Deadpool took on intergalactic bounty hunter Macho Gomez, where at the end of their battle, Deadpool commandeered his spaceship and sent Gomez to his supposed death. Unfortunately for Deadpool, he found out that Gomez was affiliated with his in-laws’ outer space towing business and soon our merc protagonist got roped into that.
The gigantic Orksa was furious with Deadpool taking out her husband, but Deadpool calmed her down with a kiss and the two ended up getting married on the spot. This was Orksa’s fourth marriage, which annoyed Obb, a coworker with eyes for her (er… eye for her because he’s a freaky alien). Obb made a couple attempts at taking out Deadpool and failed, but Deadpool spared his life when realizing Obb’s reasons for doing it. After helping some less-fortunate aliens survive a cokehead planetoid (yes, really), the two returned to Orksa, who realized that she had feelings for Obb. Deadpool divorced her, returned to Earth and noticed that he may have developed a fetish for chubby girls.
Deadpool was hired by Satana, sister of the Son of Satan (daughter of the father of the Son of Satan?). She had lost a bet with a group of nerds and was forced to marry one of them. Deadpool was cool with just killing them and going on his way, but they turned out to be human forms of various top-ranking Marvel demons like Mephisto and Dormammu. That’s where he came up with plan B: marry Satana. Hey, if they were married, she wasn’t allowed to get married to any demons!
Asmodeus ended up getting the go-ahead to pursue Satana and thought he’d deal with Deadpool’s trick by just killing him and taking care of the “death do us part” aspect of his marriage. Satana had magically enhanced Deadpool’s soul and weaponry, which was just enough to take Asmodeus down. Unfortunately for Deadpool, once that was done with, Satana had their marriage annulled and took half of Deadpool’s soul before they could even do the honeymoon mambo.
And Satana is someone who’s gotten frisky with Ghost from Thunderbolts, a guy who goes months without bathing. That’s got to hurt Deadpool right in the confidence.
In a story that takes place just a few years ago in terms of continuity, yet “came out in the ’70s,” a long-lost comic featuring an afro-sporting Deadpool teaming up with the Heroes for Hire led to him hooking up with Carmelita. Her father was killed by albino pimp the White Man and her mother hired Power Man and Iron Fist to rescue Carmelita from the kidnapper’s clutches. Deadpool insisted on joining them because he simply felt like getting in the way and being a comedic nuisance. He ended up being caught by the White Man and was sent to rot with Carmelita. The two were in the midst of some sexual action when Luke Cage burst through the wall, horrified at what he was seeing.
The heroes stopped the White Man and all was good, but once Carmelita saw Deadpool’s face, she freaked out and ran away. That should have been the end of the story, but she returned sometime later with a daughter Eleanor, claiming it was Wade’s and that she wanted some child support. He said Eleanor was too beautiful to be his and yelled at Carmelita to leave him alone…mainly for their own good.
Some time later, the sinister Butler kidnapped Carmelita and Eleanor for the sake of blackmailing Deadpool to do his bidding. Deadpool tried to liberate them, as well as the loved ones of others that Butler and the North Korean government were experimenting on, but only few survived. To his outright horror, Deadpool found Carmelita’s body in a pit of bullet-ridden victims. Witnessed by Captain America and Wolverine, Deadpool broke down and cursed himself for causing all this death just because he insisted on tagging along with Cage and Iron Fist all those years ago.
Thankfully, Eleanor is alive and well. Sadly, Deadpool caused himself to lose his memories of her and everything from the Duggan run due to trauma from the horrible mistakes he made. It’s only temporary, as in the year 2099, the two regularly fight crime together.
Most notably in the past few years, Deadpool’s main squeeze was Shiklah. Deadpool was hired by Dracula himself to unearth a slumbering succubus that Dracula was intent on marrying to bring their monster kingdoms together. Although Shiklah tried to suck Deadpool’s energies with a kiss, she was shocked to see him survive it. Together, the two went on an adventure to reach Dracula, falling for each other on the way. This worked out for the better, as Dracula changed his plans and wanted Shiklah’s death.
To screw with that arranged marriage, Deadpool and Shiklah got married on the way to fighting Dracula. Afterwards, they had a real wedding with various members of Deadpool’s supporting cast and a bunch of the superhero community showing up.
While Shiklah ruled her underground kingdom of monsters, Deadpool ducked out often to fulfill his duties as a mercenary and Avenger. While the two were crazy for each other, time had strained their relationship and a glimpse into the future shows a coming war between the two, as well as a scarred, succubus daughter who doesn’t think too highly of her father.
Shiklah ended up leaving Deadpool for Dracula anyway, but according to the flash-forward with Deadpool 2099, the two are destined to reunited and split up indefinitely.
Captain America put together the Avengers Unity team. Rogue was the team leader while Deadpool funded them. Over time, Rogue grew to respect Wade and befriend him. Finding out that his daughter Ellie was a mutant, Rogue promised to mentor her when her powers manifest. After finally defeating the Red Skull as a team, Rogue and Wade had a very brief fling. Rogue kissed him to absorb both his gross skin and his horrific memories.
Nothing much came of this situation outside of Gambit being very, very confused upon hearing about it. Any chance of them having a future went out the window when Deadpool killed Agent Phil Coulson under the orders of Captain America…who turned out to be part of Hydra. Ugh.
The Man-Thing-commanding sorceress became a permanent fixture in Weirdworld, a bizarre fantasy kingdom where time and space are all wonky. Deadpool entered Weirdworld for the sake of hunting down and killing an accountant who was laying low there. Deadpool was quick to get drawn into the Weirdworld’s weirdness and the politics of the realm. He found himself rescued by Kale, otherwise known as the Swamp Queen. The two became allies and eventually got married. Due to the way time is perceived in Weirdworld, they were together for years.
Then, when preparing to take on Morgan Le Fay’s armies, Deadpool realized that one of his own soldiers was that accountant he was hired to kill. Deadpool did so, escaped the wrath of his soldiers, then escaped Weirdworld completely. Since then, Kale has sworn her revenge.
There have been plenty of other women in the Marvel universe who Deadpool’s at least tried to get with, only to fall flat on his face. He’s hit on Cable’s old friend Irene Merryweather at least once, made a couple passes at AIM agent Dr. Betty, went on a disaster of a first date with Big Bertha, and I’m sure he’d love for Domino to give him the time of day. He’s had affection for Thunderbolts teammate Elektra, only to have his dreams crushed when he discovered that she and the Punisher were friends with benefits.
Oh, and he’s also had some very homoerotic fantasies involving giving Cable a massage on a beach. Cable has supposedly had similar thoughts and the two have agreed never to talk about it. Ever.