Everybody loves Deadpool. The fans love the Merc With The Mouth with his fourth wall shenanigans, brutal nature, and witty banter. Most heroes, on the other hand, aren't the biggest fan of Deadpool - but that's not to say the merc hasn't found some love interests over the years.
Of course, this being Deadpool, most said love interests are usually pretty strange. There really is no middle ground, whether it be him fantasizing over other heroes, otherworldly beings, or supernatural entities. Granted, most of these relationships ended up going sour but some fond and bloody memories were made along the way.
Spider-Man
Now, this "romantic relationship" is one-sided in nature, which is why it's should be more of an honorable mention. Yet, it's worthwhile to mention the Webslinger's hate for Wade.
Whether it be him trolling the Spider or not, the pair's unlikely relationship was explored over the course of Spider-Man/Deadpool where the pair ended up having a kid. Well, a cloned kid named Itsy-Bitsy who tried to kill her "dads". It added to the bizarreness of Spider-Man and Deadpool having a relationship together.
Cable
Like Spider-Man, the "relationship" of Deadpool and Cable is pretty one-sided. Deadpool's constantly showing signs of affection towards the cyborg and Cable always seems to chalk it up to Wade just messing about. At least, until Cable & Deadpool issue 20.
After being drugged by the villain Diamondback, Deadpool begins to hallucinate and sees him giving Cable a backrub on the beach. While Deadpool tries to explain to the villains that they're just friends, it makes all his advances and cracks at Cable seem a little more loving in nature and weird given the hate Cable holds against Deadpool.
Elsa Bloodstone
In recent comics, Deadpool went from being the merc with the mouth to the king of the monsters. When monsters began to occupy the likes of Staten Island, turning it into their new home, Deadpool became their king and caught the eye of monster hunter Elsa Bloodstone. Soon enough, Elsa and Wade became a couple after the stone Elsa got her powers from became corrupted, forcing Wade to help and eventually fall for her.
As a whole, the whole idea of a monster hunter falling for the newest King of Monsters just exudes strangeness. Didn't seem like much of a turn-off for them though. In one instance, after Wade was torn apart by the Queen of Bone, Elsa kissed his severed head then carried it away in a babybjorn made from her jacket. By all s, it's sweet but in no way a normal thing to happen even in a comic book relationship.
Copycat
Funny enough, Copycat and Wade's relationship was explored Deadpool. In the movie, Vanessa was a human who Wade fell for before getting cancer. In the comics, Vanessa is a blue-skinned mutant who can shapeshift and copy anyone's power.
While the movie showed Wade and Vanessa in a loving relationship, Copycat was obsessed with Wade in the comics. Constantly, she'd change herself into women Deadpool liked and try to seduce, get back into a relationship with, or even just to torment Wade, only to try to kill him when the ruse failed. The weird thing is, Wade seemed to still have something for Copycat despite her creepy attempts to get back with him, even mourning her after her death.
Typhoid Mary
There's a time when strange just becomes creepy. For a while in comics, Deadpool was dating the mutant Siryn, daughter of Banshee, with the pair having a solid relationship. However, that love was exploited by the mutant Typhoid Mary.
At one point, Mary disguised herself as Siryn and slept with Deadpool, with him unaware. Even stranger is that Mary saw this as her paying Deadpool back for pulling off a job, not as the sexual assault that it actually is.
Mercedes Wilson
Relationships in comics can always get to be incredibly convoluted. For a while, Wade started seeing a woman in hallucinations. Eventually, Wade comes across the woman who's revealed to be Mercedes Wilson, his wife. Deadpool and Mercedes end up continuing their relationship for some time. Or so it seems.
As the comic continues to unfold, it's revealed that Deadpool isn't really Wade Wilson. Wade Wilson may be his arch-enemy, a man named T-Ray who Deadpool was sent to kill years ago. In the process, he killed Mercedes Wilson, T-Ray's wife. Vowing revenge, T-Ray resurrected Mercedes, set her up as Wade's wife, then revealed everything to torture Deadpool. Even stranger was that Mercedes seemingly developed some feelings for Deadpool, despite the convoluted plot and relationship.
Orksa
Beyond being a mercenary on earth, at one point, Deadpool ventured off into the far reaches of space to become a bounty hunter. In one instance, Wade became married to the alien Orksa after just kissing her, causing the alien to assume it was a marriage proposal and accepted.
Even though Deadpool was marrying an eight-foot-tall yellow-skinned alien after just a single kiss he didn't seem all that upset over it and the pair remained married for a short while. Of course, Deadpool being Deadpool, the pair eventually got a space divorce and Wade returned to earth as Orksa married another alien, Obb.
Satana Helstrom
Leave it to Deadpool to get into bed with the daughter of the Devil. When Satana Helstrom lost a game of poker (and her soul with it), she went to Deadpool for help. However, Deadpool turned the tables on Satana and ended up binding their souls together and marrying her.
While the other relationships felt strange due to who Deadpool was dating, this one feels strange mainly because of the means. After all, Wade and Satana were falling for each other because of a demonic contract. Eventually, Satana did divorce Deadpool and regain her soul.
Shiklah
Of course, Deadpool didn't let those failed Marvel marriages stop him. After Orksa, Mercedes, and Santana, it would be easy to think Deadpool wouldn't marry again. But that didn't stop it from happening when Deadpool was sent on a job to kill the Queen of the Undead, Shiklah.
When the pair first crossed paths, Shiklah, for obvious reasons, tried to kill Wade by draining his life force via a kiss. However, due to Deadpool being Deadpool, he survived and impressed Siklah so much, the pair ended up getting married. What followed was an up-and-down and bizarre relationship filled with demonic torture/sex games, monstrous shenanigans/date nights, and a final battle to the death/divorce.
Death
It seems almost ironic that Deadpool and the embodiment of Death were a thing. Dying constantly and always coming back probably did the trick and somewhere along the comic line, Deadpool and Lady Death became a couple. Even if it is utterly bonkers for someone to be dating the embodiment of Death.
The pair had a constant on and off relationship, sometimes hooking up and then dumping one another. There was also the time Death hooked up with Thanos, which put him and Deadpool forever at odds but beyond that, the pair had an interesting and strange relationship, to say the least.
