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Deadpool's Strangest Romances, Ranked

Romance, thy name is the regenerating degenerate - The Merc With a Mouth - Wade Wilson, the one and only Deadpool! But while a rose by any other name would smell just as sweet, something's gone rotten in the state of Deadpool's love life, and it's really starting to stink up the place! It may be true that the course of true love has never really run all that smoothly, but while many star-crossed lovers have found their romantic stories becoming tales of woe, few have been subjected to the degree of serial romantic tragedy to which Wade has endured. The only thing more dependable than Deadpool's lovers being strange is their propensity for destroying Wade's romantic aspirations.

It's fortunate that Wade has a healing factor given that he has his heart broken on an astonishingly regular basis. But while dealing with dashed romantic dreams would be bad enough, Deadpool's love life is also filled with a cavalcade of completely crazy companions! Wade's ex-girlfriends run the gamut from mutants to aliens to physical incarnations of abstract concepts, and that's only the shallow end of the merc with a mouth's dating pool. From ex-wives to ersatz girlfriends, Deadpool has suffered no shortage of off-the-wall lovers during his career as Marvel's most metafictional mercenary, and in some instances, they're thirsty for revenge after their respective relationships with Wade ended in spectacular fashion. Take off the katanas and put on your personal mix of heartfelt 1980s power ballads, because CBR is ranking Deadpool's 20 strangest romances.

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20 GRETCHEN WILSON

One has to suspect the most unusual thing about Gretchen Wilson is h0w little is known about her relationship with Wade. Gretchen is one of Deadpool's two ex-wives and appears only in the 5-issue miniseries Identity Disc (2004) by Robert Robi, Sandu Florea, John Higgins, and Estudio Fenix.

The story revolves around a team of mercenaries attempting to steal the eponymous disc, which contains confidential information on every superhero in the Marvel Universe. Deadpool hopes the information will lead him to his ex, but considering the fact that she has yet to appear in another panel, it seems that in this instance, Wade's effort was for naught.

19 DOCTOR BETTY SWANSON

Deadpool met Dr Betty Swanson in Deadpool: Merc with a Mouth #1 (2009) by Victor Gischler, Bong Dazo, José Pimentel, and Matt Milla. Swanson was working as for A.I.M. as a double agent and infiltrated a HYDRA expedition to search for effective toxins amid the natural and untamed resources found in the Savage Land.

A.I.M. hired Wade to travel to the Savage Land and retrieve both Swanson and the "package" that had been the object of her original mission before HYDRA returned to claim the prize for themselves - a prize that turned out to be an animated, zombified version of Deadpool's head.

18 DOCTOR MATSUZAKI

In Deadpool #30 (2011) by Daniel Way, Bong Dazo, Jose Pimentel, and Andres Mossa, Wade meets Dr Matsuzaki when she gets caught in the crossbow-fire of a war between two gangs of vampires (or two gangs of "Draculas," as Deadpool insists on calling them).

While Wade is immediately smitten with Matsuzaki, his affection for her remains unrequited: although she tells him that she's willing to go out on an ice cream date with him, she vanishes before they get the opportunity to share a sundae. Deadpool's heart may have been broken once again, but at least he has the voices in his head to keep him company!

17 MS MARVEL

Ms. Marvel

In the Deadpool #27 (2013) story "#$%@-Faced in Vegas" by Brian Posehn, Scott Koblish, and Val Staples, Deadpool recounts a 1980s weekend in Vegas. When an invasion of grotesque mind-controlling aliens takes place on the Strip, Wade must team up with Ms Marvel to save the day!

After the aliens have been defeated, Carol and Wade head to a nearby wedding chapel to tie the knot. But Deadpool's romantic dreams are dashed when Captain American arrives to speak with Ms Marvel. He discovers that Carol has one of the disgusting alien creatures controlling her actions, and her nuptials with Wade are subsequently canceled!

16 ILANEY BRÜKNER

Wade meets Ilaney Brükner in Deadpool #18 (1998) by Joe Kelly, Walter McDaniel, John Livesay, and Chris Sotomayor. Originally from Germany, Brükner has exiled herself to a remote cabin after a plane she was piloting crashed, costing the lives of two hundred passengers.

While resistant to Deadpool's romantic advances, Brükner nevertheless assists Wade in his adventures, eventually offering him her services as a pilot. Unfortunately, she ultimately falls victim to the ongoing battle between Wade and his nemesis, T-Ray, who curses her to re-live the plane crash repeatedly in retaliation for interfering with his complicated plan for revenge on Deadpool.

15 DOMINO

While it wasn't the first time they had crossed paths, Domino uses Deadpool's romantic feelings to her advantage - and the advantage of the X-Men - in Deadpool #17 (2009) by Daniel Way, Paco Medina, Juan Vlasco, and Marte Garcia. When Wade resolves to join the ranks of the X-Men, Xavier's team of self-righteous mutants face a PR crisis.

In order to subdue the merc with a mouth before he brings more negative attention to the X-Men, Domino feigns amorous intent. Deadpool is suspicious, but can't pass on the opportunity to invite Domino up to his hotel room. The charade doesn't last long, as she capitalizes on Wade's lowered defenses and knocks him unconscious.

14 SIRYN

Siryn in X-Factor

Deadpool and Siryn of the X-Men had something of an ongoing romance throughout some of Wade's earliest appearances. As a member of X-Force, the daughter of mutant Banshee had the opportunity to cross paths with the regenerating degenerate, and she soon guests starred in some of the first books headlined by Deadpool.

In Deadpool #3 (1994) by Joe Kelly, Ed McGuinness, Nathan Massengill, Norman Lee, Matthew Paine, and Digital Chameleon, Wade enlists Teresa's help to seek vengeance against her cousin, Black Tom. Although Siryn often tells Wade she has no amorous interest in him, the potential for romance increases in later issues, when Deadpool begins displaying more heroic tendencies.

13 MERCEDES WILSON

Mercedes Wilson first appears in Deadpool #26 (1999) by Joe Kelly, James Felder, Pete Woods, Walden Wong, and Shannon Blanchard. At first, Deadpool recognizes her face but cannot determine how he knows her.

Eventually, it is revealed that Mercedes was Wade Wilson's late ex-wife, who had been resurrected by the villainous T-Ray as part of his plan for vengeance against Deadpool. However, later revelations suggest that T-Ray had originally be called Wade Wilson, making it unclear precisely who it was that had been married to Mercedes. Romance is always complicated, and doubly so when it comes to the love in the Marvel Universe!

12 OUTLAW

Wade and Inez Temple first met in Deadpool #65 (2002) by Gail Simone and Udon Studios. A mutant with superhuman strength, Outlaw faced bullying when her powers first manifested during adolescence, and she loathed the nickname given to her by her tormentors: "Crazy Inez."

In the Deadpool #27 (2013) story "Eulogy for a Winkie" by Gail Simone, Alvin Lee, and Veronica Gandini, Outlaw's former lover Alex tries to warn Wade about the dangers of combining her superstrength with physical affection on the day of Wade and Inez's wedding. For better or worse, Deadpool is unable to take this extremely painful lesson to heart until he learns it firsthand.

11 TYPHOID MARY

Typhoid Mary Jessica Jones rumor

In Deadpool #6 (1997) by Joe Kelly, Ed McGuinness, Norman Lee, Nathan Massengill, and Chris Sotomayor, Wade is hired by Typhoid Mary, a supervillain with a split personality, as protection from an assassin hired by her other personality, but the pair parts when Mary suggests Wade will never become the hero that Siryn believes he can be.

In Deadpool #13 (1998) by Kelly, Pete Woods, Massengill, and Kevin Tinsley, Wade discovers that what he thought was the physical consummation of his relationship with Siryn was actually an act of affection with Typhoid Mary in disguise. The revelation leaves psychic scars that Wade still struggles with decades later, as seen in Part One of Deadpool #13 (2016) by Gerry Duggan, Jacopo Camagni, and Veronica Gandini.

10 SATANA HELLSTROM

In Deadpool Team-Up #892 (2010) by David Lapham, Shawn Crystal, and John Raunch, Satana Hellstrom is playing a game of poker when she discovers her opponents are among the most powerful demons of the underworld. After the demons win Satana's soul in the game, she and Wade get hitched as part of a scheme to ensure that her demonic enemies are unable to claim her hand in marriage.

Satana's mission is a success, thanks in large part to Deadpool's skills with a sword. Nevertheless, the marriage ultimately ends in divorce. In her parting letter, Satana explains that she now rightfully owns half of Deadpool's soul.

9 ANASTASIA

In Deadpool #46 (2000) by Jimmy Palmiotti, Paul Chadwick, Ron Randall, and Shannon Blanchard, Wade meets Anastasia at a tattoo parlor. Deadpool is surprised that she does not seem to be repulsed by his appearance, and the two begin to kindle a romance.

However, it is later revealed that Anna was a mobster's girlfriend who had hoped that she would be able to use Wade's mercenary skills to assassinate the mobster and cash in on his insurance policy. In an extremely cold moment, Deadpool betrays his lover before she has the chance to execute her plan, telling her that she never knew the real Wade as he does so.

8 COPYCAT

Also known as Vanessa Carlysle, Copycat is a mutant with shapeshifting abilities who was Wade Wilson's girlfriend before he became Deadpool. A member of X-Force whose tumultuous relationship with Wade often comes back to haunt the merc with a mouth, Copycat is not above taking the form of Deadpool's late lovers in order to manipulate his emotions.

In the Deadpool #27 (2013) story "Quickie," by Jimmy Palmiotti, John Timms, and Veronica Gandini, Deadpool thinks he has reunited with Anastasia, who is surprised to discover had survived his seemingly fatal betrayal of her trust. Unbeknownst to Deadpool, the reader learns at the conclusion of the short tale that it wasn't the late Anna, but rather Wade's ex Copycat in disguise!

7 BROKEN BLADE ("B.B.")

First appearing in Deadpool Corps #4 (2010) by Victor Gischler, Rob Liefeld, Adelso Corona, and Matt Yackey, Broken Blade was a disgraced intergalactic assassin running a nightclub when she met Wade. While the pair begin by fighting, they quickly retreat to her private quarters.

After Deadpool gives her the nickname "B.B.," she admits that while she enjoyed her time with him, her primary motivation in connecting with Wade is to capitalize on the association with the growing infamy of the Deadpool Corps. Fortunately, the romantic tryst also gives Deadpool a chance to show off his tasteful if somewhat understated Hulk boxer shorts.

6 CARMELITA CAMACHO

In Deadpool #13 (2013) by Gerry Duggan, Brian Posehn, Scott Koblish, and Val Staples, a groovy, retro version of Wade finds love on the streets on 1977 New York City while trying to join the Heroes for Hire team. While facing off against a nefarious villain known as the White Man, Wade is captured and imprisoned alongside Carmelita Camacho.

Eventually, Luke Cage arrives and frees them both from imprisonment, but they pair have already gotten intimate by the time he arrives. It was only years later that Deadpool learned that Carmelita had subsequently birthed their daughter, whom she raised in secret!

5 YELENA BELOVA

Natasha Versus Yelena

In Deadpool #9 (2009) by Daniel Way, Paco Medina, Juan Vlasco, and Marte Gracia, which takes place during the Dark Reign event, Wade develops a serious crush on Black Widow, which was the codename for Yelena Belova during her time on Norman Osborn's Thunderbolts team. He pursues her relentlessly, even going so far as to fly a banner with his phone number in the skies above the Big Apple.

While Deadpool does use his teleporter to steal a kiss from Yelena at one point, the strangest thing about this romance is that Wade's advances eventually begin to find some success.

4 BIG BERTHA

In the pages of the Deadpool/GLI Summer Fun Spectacular #1 (2007) is "A Date with Density" by Dan Slott, Fabian Nicieza, Paul Pelletier, Dave Meikis, and Wil Quintana. In an effort to get Wade off of their couch, the Great Lakes Avengers send Big Bertha to distract him from his cartoons by seducing him with her feminine wiles.

Wade is ecstatic when Bertha invites him on a date but is visibly disappointed when the shapeshifter arrives in the guise of her svelte supermodel form. When Bertha inflates her body to deal with some superheroic responsibilities during their dinner, Wade is delighted, but Bertha realizes that she can't sustain a romance with someone who is only attracted to her because of her body.

3 ORKSA

It's a tale as old as time in Deadpool #33 (2011) by Daniel Way, Carlo Barberi, Walden Wong, and Marte Gracia: after defeating her late husband in battle, Deadpool meets the claw-handed alien Orksa at the Funtzel Intergalactic Towing & Recovery station, and becomes married to her when he kisses her to relax her.

When Obb and Deadpool begin working together, Orksa suspects Obb is up to no good -- and she's absolutely correct. Fortunately, Orksa follows her instinct and ultimately rescues Deadpool from Obb's villainous machinations! Unfortunately, she falls in love with Obb during Deadpool's convalescence and ends up leaving Wade for him.

2 DEATH

Marvel Death

The affinity that the embodiment of mortality shares with Wade was first revealed in Deadpool and Death Annual #1 (1998) by Joe Kelly, Steve Harris, Reggie Jones, and Chris Sotomayor. After a number of near-fatal experiences, the romantic interest between Death and Deadpool begins to kindle into something more serious.

However, Death's mutual feelings for Deadpool are not enough to overcome the ire of her other romantic interest, the infamous supervillain Thanos! Jealous of Death's affection for Deadpool, Thanos dooms Deadpool to remain forever apart from his lady love, a curse which comes with the unfortunate side effect of making Wade near-immortal.

1 SHIKLAH

Deadpool Shiklah hell double check

Deadpool first meets Shiklah in the seven-issue miniseries Deadpool: Dracula's Gauntlet (2014) by Gerry Duggan, Brian Posehn, Reilly Brown, Scott Koblish, and Khary Randolph. Dracula hires Deadpool to track down the demon queen who he has decided is his bride to be. But when Wade locates Shiklah, he discovers that she has no interest in being Dracula's betrothed, and the two soon fall for one another.

The strangest thing about this romance might be how well Shiklah and Wade get along - it may not be a match made in heaven, but the pair seems weirdly well-suited to one another. What could possibly go wrong?

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