Deadpool isn’t a character that Marvel Comics fans would normally associate with romance. However, as with any major character with decades’ worth of history, Wade Wilson has had his fair share of entanglements with other characters. From his own recurring characters to other superheroes, the Merc with the Mouth has gotten involved with a lot of different people.

Related

Marvel: 6 Worst Things Deadpool Has Done

Deadpool seems like an anti-hero, but in reality, with some of the actions he has taken over the years, he could easily be considered a villain.

As a member, not just of the general X-Men Universe, but also of a number of different teams over the years, in spite of his lone wolf moniker, Deadpool has had a surprising number of opportunities to have relationships with different characters over the years, and more could appear beside him on-screen now that Deadpool 3 will be a major part of the MCU.

10 Rogue

True Acceptance

• First Appearance: Avengers Annual #10
• Creators: Chris Claremont, Michael Golden

The only major member of the X-Men that has been romantically linked at all with Deadpool, Rogue, was only with Wade for a brief time. However, in spite of the fling-like nature of their romance, this was a major moment for Deadpool emotionally.

Despite his variety of strange romantic connections, Deadpool wasn’t often accepted for his deformities. Following Rogue almost beating him to death, she kissed him and truly didn’t seem to care that she started to absorb his skin deformity while kissing him. Rarely has Deadpool had such a deep connection, despite it being such a short romantic link. Hopefully, these two will meet cinematically with Rogue probably joining the MCU soon.

9 Carmelita Camacho

Mother Of Deadpool’s Child

• First Appearance: Deadpool Vol.5 #13
• Creators: Brian Posehn, Gerry Duggan & Scott Koblish

Deadpool’s daughter has been a significant aspect of more recent comic book runs, making Carmelita, the mother of his daughter, a more enduring figure in his life than some of his other brief romantic flings. When she first showed him his daughter, Wade refused to have anything to do with them.

However, years later, a Weapon X Scientist finds Carmelita and has her brutally murdered. Deadpool actually came to try and save her but found he was too late and actually had an emotional moment with her, before making his daughter a bigger part of his life going forwards. There have been various child versions of Deadpool, but his daughter appearing as a major part of his life was a huge shift for Wade.

8 Carol Danvers

Almost Deadpool’s Wife

• First Appearance: Marvel Super Heroes #13
• Creators: Roy Thomas, Gene Colan

Captain Marvel, although the events in question took place before she gained that moniker, nearly married Deadpool. After fighting off mind-controlling aliens, Deadpool and the then Ms. Marvel bonded and very nearly married each other in Las Vegas.

Admittedly, Ms. Marvel was not only drunk but also under mind control by an alien during the proceedings, and Captain America luckily arrived in time to break them up. But still, this strange entanglement is one of the more high-profile “relationships” that Deadpool has ever had throughout Marvel Comics, and they could run into each other in the MCU at some point.

7 Satana Hellstrom

Brief Wife

• First Appearance: Vampire Tales #2
• Creators: Roy Thomas, John Romita Sr.

Deadpool has had a lot of weddings and "almost weddings". While he is known for some strange relationships, this one was on the next level. He had a whirlwind romance with Satana Hellstrom, the daughter of Satan. When she was forced to decide which of her father’s demons to marry, Satana decided Deadpool would be a better option.

Related

Marvel: Deadpool’s Best Friends, Ranked

Deadpool has a long comic book history of irritating people, but in spite of that, he has a surprisingly long list of good friends.

After infusing Wade with more power, so he can kill her other demonic suitors, Satana marries Deadpool. Unfortunately, she wasn’t actually that interested, and she had the marriage annulled before stealing half of his soul and leaving him forever. Not the ideal or typical marriage, but Wade certainly had a fun adventure with Satana.

6 Outlaw

Another Wife

• First Appearance: Deadpool Vol.3 #65
• Creators: Gail Simone, Udon Studios

The Merc with the Mouth certainly gets around a lot of different wives. It can be difficult to keep track of all the wives he has had, but Outlaw was definitely one, even if it was another brief relationship. Outlaw is a mutant with super-strength who Deadpool cheated on, before redeeming himself and eventually getting married to her.

However, super strength is a tricky power to control at certain moments, and the newlywed couple had a fairly traumatic time trying to consummate their marriage. Another annulment of the marriage followed pretty swiftly, as Deadpool and her both decided it would be better to forget the whole embarrassing situation.

5 Ananastasia Rinaldi

Could Have Really Loved Him

• First Appearance: Deadpool Vol.3 #46
• Creators: Jimmy Palmiotti, Paul Chadwick

If Deadpool has proven himself an untrustworthy companion on various occasions, he finally meets his match in Anastasia. This tattoo artist initially said she loved Deadpool’s scarred face, and they fell hard for each other, but it turned out that Anastasia had been using him.

In the end, she wanted Deadpool’s assistance in getting a life insurance payout for her horrible boyfriend. But she tried to redeem herself to Wade, handing him a gun and telling him that if he truly believed she didn’t love him, then he should shoot her. Unfortunately, she’d burned Deadpool just a little too much, and he did actually shoot her, never finding out if she could have truly loved him.

4 Lady Death

Actually Death

• First Appearance: Marvel Mystery Comics #10
• Creators: Jack Kirby, Joe Simon

Deadpool courts death, in the regular sense, but he has also courted Death, literally. Lady Death is an actual character in the Marvel Universe, and she became fascinated with Deadpool after meeting him during several near-death experiences Wade had. Of course, because it was Deadpool, he fell in love with her and sought to court her.

Unfortunately for Wade, he wasn’t the only one intrigued by Death. Thanos himself was also courting Death, and as a form of vengeance for her preferring Wade, Thanos cursed the Mercenary with immortality. This meant that Deadpool and Death could never be together, which was heart-breaking, but also probably for the best. The relationship couldn’t have been all that great for either of them.

3 Valentine Vuong

Current Partner

• First Appearance: Deadpool Vol.9 #1
• Creators: Alyssa Wong, Martin Coccolo

The current love interest of Deadpool has been a very fun addition to his series. Alyssa Wong’s run on Deadpool has been hilarious, and Valentine Vuong, a non-binary assassin character, has been the best addition made in this most recent take on the character and his world.

Related

Best Marvel Games With Playable Deadpool

It can't be easy incorporating a character as strong as Deadpool into a game, but this hasn't stopped the merc from making a few appearances.

Fitting perfectly in many ways with Wade, Valentine is a very cheerful character with a sadistic hidden nature, but they couldn’t help becoming smitten with Deadpool during their time working together. Despite being another character that was just using Deadpool, Valentine gained true feelings for Wilson and was forced to admit it, leading to the pair properly dating, making for a pair of perfect nihilists.

2 Copycat

Original Paramour

• First Appearance: New Mutants Vol.1 #98
• Creators: Fabian Nicieza, Rob Liefeld

Copycat, the comic book version of the Deadpool movie character Vanessa, was a long-time love interest for Wade. A shape-shifter in the comics, Copycat was originally dating Wade Wilson when he was first diagnosed with cancer. She left him after this in the comics, but stayed with him in the cinematic version of the character, until her eventual death, meaning she might not return in Deadpool 3.

In the comics, Copycat would return to torment Deadpool later in his life by taking the form of his other former lovers. This turn in their relationship helped make Copycat memorable for comic readers, as most of Deadpool’s other lovers didn’t make much of an impact on his life following their breakup. This pair has a lot of history.

1 Mercedes Wilson

Actual Wife

• First Appearance: Deadpool Vol.3 #26
• Creators: Joe Kelly, James Felder & Pete Woods

The most significant of all the many wives that Deadpool has had over the years, Mercedes Wilson was married to Wade until the pair took in a man who claimed to be the real Wade Wilson before he killed Mercedes. Though she was later resurrected, she was confused and left Wade forever to be with the other man.

This confusing twisting story aside, Mercedes and Wade were actually in a fairly uncomplicated and happy marriage for a length of time. This almost certainly makes it the longest relationship that Deadpool has ever been in, and the one with the least amount of murderous romance.

MORE: Marvel: Wolverine's Best Friends