Death and Deadpool have a pretty complex relationship that has been on and off since Deadpool pretty much became the Deadpool fans know him as today. Death and Deadpool fell in love with one another in a pretty strange and unique way and have a ton of dynamic situations that have caused the pairing to become closer and further apart.
A lot of fans consider Death to be Deadpool's true love as Mary Jane is for Spider-Man or Louis Lane is for Superman. For Deadpool to be in love with Death as an immortal being creates a ton of problems that Merc with the Mouth constantly tries to overcome, so that he may finally be with his one true love.
10 Tortured As Weapon X
The way the two fell in love is pretty extreme. At Weapon X, Wade Wilson was tortured all the time, being so close to the literal death that he ended up meeting Death herself. The two got to know one another at this time and Wade ended up becoming totally infatuated with her. The two bonded closely and eventually, it was revealed that Death had fallen in love with Wade as well. The two would often see one another whenever he came near death and appears to him on several occasions.
9 Thanos Keeps Getting In The Way
However, the couple almost immediately meets turmoil as the Mad Titan known as Thanos also has a deep-rooted love for Death, a love that she does not reciprocate. Thanos is pretty much obsessed with Death, and though she admires him and his total destruction, she doesn't really love him in that way. Thanos continuously tries to snatch Death away from Deadpool and grows increasingly more jealous as their relationship moves on.
8 The Curse Of Immortality
Eventually, Thanos ends up cursing Deadpool with immortality, making it so that he could never die and never officially be with Death. Deadpool does a number of things to get around this but nothing ever seems to work. His regeneration becomes too powerful and nothing stops it from coming together again, save for total disintegration. This makes a strain between Deadpool and Death as they end up only able to see one another when Deadpool gets into near-death situations.
7 They Want What They Can't Have
Because of their strained meetings that don't really occur too often, Death and Deadpool end up yearning for each other even more. The two meet on several occasions, sharing fleeting moments and dreams with one another throughout the years. This makes them only want each other more.
Deadpool tries several times to off himself in order to be with he. He feels done with his life and will happily give his soul to Death if that meant he got to spend more time with her.
6 They Understand One Another
The two really understand one another, which is odd considering who and what they are. Death is an ancient promise, Deadpool is an immortal fool. But even through that, they both understand that the other is needed at different times in different places. They understand each other's emotional needs and try to be the best that they can for one another. Deadpool enjoys his fun dreams with her and tries to make them worthwhile so they can create memories together.
5 She Gets His Humor
Surprisingly, Death totally gets Deadpool's humor. Deadpool is iconically humorous as he constantly breaks the fourth walls and never seems to not be joking. Death is thought to be this all-powerful, serious being, but in reality she finds him utterly hilarious and plays off his jokes. There is an iconic panel between the pairing where Deadpool explains his next attempt at dying and how it's going to be really hard, to which she responds, "That's what she said."
4 The Only Man Who Can Handle Her
On the same token, Deadpool really seems like the only man who could handle Death. Thanos wishes he could, but she seemingly finds him more like an obsessed stalker than an actual love interest. Those two once shared a kiss that created The Rot (which they thought of weirdly as their love child) and seemingly didn't continue any form of a relationship.
Deadpool, however, can withstand Death. Literally. He is the one person that can be with her before and after he dies.
3 Curse Lifted
At some point, Thanos lifted his curse on Deadpool which allowed for Death and Deadpool to finally be with one another. He could still regenerate and it isn't too clear on how the comics handled this, but pretty much the curse was "lifted." However, by this time, Deadpool and Death were actually pretty strained from one another. They had broken up and "officially" called an end to their relationship. At that point, Deadpool went on to date (and marry) the succubus Shiklah before they became estranged and she ended up marrying Dracula instead.
2 Relationship Strained
Deadpool and Death never really seemed to recover once the curse was lifted. They never fully reconciled or met with one another again. That is, until the recent Deadpool: The End. In this comic, Deadpool actually does a 180 and actually attempts to find a way to kill Death. He does this because he meets his now-97-year-old daughter who is on the brink of death. He wants to kill Death to prevent her from dying, but as Deadpool's daughter, she has a different plan. She brings a bomb that is sure to kill them both, destroy every atom of their beings, so that Deadpool doesn't have to outlive his daughter, continuing to suffer. The bomb goes off and in that panel, Death stands behind them with her hands on their shoulders.
1 Finally With Death (Maybe?)
The ending of this comic is very much in Deadpool fashion. It has multiple endings so that fans can choose which they like most. The main ending, and the coolest one by far, actually has Deadpool and Death reconnect as he becomes the King of Hell and the two are fully themselves again. Deadpool got his girl and the two are finally able to be together in the most Deadpool and Death way possible. However, there is another ending where the two date for years and years and Deadpool seems to have gotten fat and lazy. Death then tells him she is going to get coffee with Thanos and "not to worry." The real ending is pretty unknown, but we would like to believe the cool scene of Deadpool sitting on the throne is where his story leaves off to lead fans to the upcoming King Deadpool which comes out this October.