Over the years, Deadpool has had quite a few relationships, from silly one-shot flings to brief flirtations with more dramatic characters. He's almost even hooked up with other major heroines like Rogue.
While Deadpool's relationship with one woman was the emotional backbone of both of his movies, all of his comic book relationships haven't been quite so impactful. Now, we're going to take a quick look back at some of his most serious or otherwise noteworthy romantic partners.
COPYCAT
Vanessa shares much of her origins with the movie version of Deadpool's girlfriend, including her name. But after Wade left her because of his cancer, she had a much different life. Elsewise known as Copycat, she was a shape-shifting mutant who eventually became a mercenary herself. She had a complicated history with Wade that saw them growing closer and further apart over time.
Ultimately. Wade's developing feelings for Siryn threw their relationship off. Copycat was eventually captured by Weapon X and used as a weapon. She was eventually targeted by the organization, who hired Deadpool to help unknowingly bring her down. Despite Wade's best efforts, she was killed by Sabertooth and died in Wade's arms. However, it's since been revealed that she actually survived her apparent death and has been living a quiet life running a taco truck ever since.
SIRYN
Theresa Cassidy, who's better known as Siryn, is the daughter of Sean Cassidy, the X-Man Banshee. Like her father, she can unleash a sonic scream that can reach levels so high or precise that she can bring down a wall or even fly. She first encountered Deadpool as an enemy and while dealing with a romantic interest in her teammate Warpath.
Siryn even saw beyond his scarred body, but he quickly became creepily infatuated with her. It was his dedication to being good enough to be with her that first motivated Deadpool to try and become something more than just a mercenary. The two drifted apart as she grew closer with Warpath. However, the pair remained friends and allies, and even had a one-night stand while she was trying to move past her own personal drama with Jamie Madrox. She even attended his wedding to Shiklah.
MERCEDES
After having many of his memories restored while fighting a cosmic power, Wade comes to the conclusion that a woman in some of his memories is his former wife. After Wade found her, he learned from the Black Talon that she had been previously dead, but the pair try to learn more about what happened. Wade believes that the pair had led a simple and happy life until the mercenary T-Ray came across them. He killed Mercedes and pushed Wade to become the man he is.
However, it was subsequently revealed that it was reversed: T-Ray and Mercedes had been married, while Wade was the mercenary. T-Ray brought her back to torture Deadpool, but she was disgusted with her husband for the purpose behind bringing her back. Deadpool apologized for the act, however, telling her she was the only person he ever killed that he regrets. The event has been retconned and changed over the years. but that original story ended with Mercedes finding a sense of forgiveness for Wade but telling him in no uncertain terms that she never wants to see him again.
OUTLAW
Inez Temple is a mutant blessed with enhanced strength. She became a mercenary in her adulthood and one of Deadpool's professional peers. She became a frequent (and flirty) ally of Deadpooland his friends, although her relationship with Deadpool wasn't as intense as the connection that grows between her and Alex Hayden, who was known as Agent X (who'd been briefly fused with Deadpool and Black Swan and gained some of his personality as a result.)
She and Wade eventually hooked up during the events of Deadpool: Suicide Kings after she saw how big his heart really was. The pair were even briefly married, although the marriage was annulled after Wade's healing factor was revealed to not be physically capable of keeping up with her. The two remain allies though, with her being supportive of his other relationships.
CARMELITA
Carmelita Camacho was the daughter of a store owner in New York City. After he was killed by the White Man, the Heroes for Hire (and Deadpool) were hired to avenge him. Carmelita and Deadpool were captured by the White Man, and forged a quick bond. Carmelita, believing she wouldn't survive the experience slept with Wade while they were in captivity.
After the heroes brought down the White Man, Carmelita saw Wade's face and fled. Unbeknownst to Wade, she was pregnant and subsequently gave birth to a girl named Eleanor. When she informed Deadpool, he didn't believe that anyone so beautiful could have come from him. He sent her running away, and she raised Eleanor alone. However, the pair were kidnapped by Deadpool's programmer Butler and used as collateral against Deadpool. While Eleanor would be saved, Deadpool only found Carmelita's body.
SHIKLAH
After her powerful demonic family was killed, Shiklah was sealed away in an enchanted coffin. Eventually, Deadpool was hired to bring her to Dracula, but Deadpool accidentally released her. The pair eventually grew closer, with Shiklah eventually developing romantic feelings for him. The pair were even married in New York City and became the rulers of a demonic kingdom underneath New York City.
However, their relationship slowly falls apart as he becomes more and more heroic. Shiklah ends up declaring war on humanity after one of her subjects is killed, and when Deadpool fights for humanity their relationship fully falls apart. The war ultimately ends with peace and the two go their separate ways, although Shiklah leaves him by admitting that there's a possibility that they may end up together again some day.
DEATH
Death is the abstract concept of death itself, who occasionally takes a female humanoid form. This is the figure that Thanos fell in love with and pushed him to become the Mad Titan that he would become. But along the way, she also found another potential love in Deadpool. When he was first being experimented on by Weapon X, Deadpool found himself looking into the face of death on the regular.
Death slowly grew fond of Wade, but could never claim him thanks to his healing factor. But any time Deadpool briefly died, he was given a brief time with Death. However, a jealous Thanos saw Wade as a potential threat to his courtship of Death and used cosmic powers to make him functionally immortal.