Wade Wilson, better known as Deadpool, has built a career out of two things: talking until his enemies’ ears bleed and killing them with the enthusiasm of a raccoon that just discovered espresso. Yet for all his chaotic swagger, the Merc with a Mouth hides a surprisingly soppy romantic streak—one that has dragged him into love triangles involving a cosmic embodiment of death and the wife of New York’s most dangerous crime lord. In 2026, with Deadpool still lurking somewhere in the Marvel Cinematic Universe and his comic back catalogue reread by fans hungry for mayhem, it is worth remembering that his love life is less a rom-com and more a Greek tragedy performed by a drunk mime. Thanos and Kingpin are not just villains; they are jealous suitors who will rearrange reality or break a city for the people they love. Deadpool, naturally, has made the baffling decision to flirt with both of their love interests.
Thanos: The Mad Titan Who Lost a Girl to a Guy in Red Spandex
Thanos’s famous love interest is Mistress Death, the cosmic entity who first made fans’ jaws drop in Marvel Comics’ Infinity Gauntlet by Jim Starlin and George Perez. Thanos proves his devotion by using the Infinity Gems to extinguish half of all life in the universe in Death’s name. That is not a bouquet of roses; that is a genocide with a greeting card. Unfortunately for Thanos, Death never returns his affection. She is not incapable of love, though. She simply falls head over heels for Deadpool. This is roughly equivalent to a god building a cathedral for a goddess, only for her to run off with a clown who keeps honking a bicycle horn during the vows.
In Thanos vs. Deadpool by Tim Seeley and Elmo Bondoc, Thanos responds with the pettiness of a billionaire whose yacht has been keyed. He makes Deadpool permanently immortal so that the merc can never be with Mistress Death. Then, because immortality does not make a great apology, Thanos beats him into a bloody, unkillable pulp out of extreme jealousy. Deadpool’s relationship with Mistress Death is therefore not just doomed; it is a cosmic restraining order written in bruises.
Kingpin: The Crime Lord Whose Wife Got a Deadpool Detour
Before Deadpool’s romantic connection with Mistress Death reached its violent climax, the Merc with a Mouth had already moved in on Kingpin’s wife years before the two were married. In Daredevil: Deadpool Annual ‘97 by Joe Kelly and Bernard Chang, Deadpool and Daredevil join forces to take down Typhoid Mary—until Deadpool betrays Daredevil to hook up with their target. This is the romantic equivalent of being invited to help put out a fire and then using the hose to fill a kiddie pool for a date.
In current Marvel Comics, Kingpin and Typhoid Mary are married. So while Deadpool’s romantic relationship with Typhoid Mary does not put him in Kingpin’s crosshairs in the same way as his fling with Death puts him in Thanos’s, he pays for it differently. When Deadpool falls in with Typhoid Mary, she uses him to betray his partner and then dumps him the second she is free. It is a masterclass in being a pawn, a patsy, and a punchline all at once.
A Table of Terrible Romantic Decisions
| Love Interest | Villain Rival | What Deadpool Did | What It Cost Him |
|---|---|---|---|
| Mistress Death | Thanos | Wooed the cosmic embodiment of death | Immortality, a savage beating, and a permanent cosmic cockblock |
| Typhoid Mary | Kingpin | Betrayed Daredevil to hook up with her | Used, betrayed, and dumped once she was free |
Deadpool pays dearly for both romantic involvements that make him the rival of Thanos and Kingpin in different ways. The dalliance with Kingpin’s future wife does not involve Kingpin directly, but Deadpool gets involved with a villain who will eventually fall in love with someone as despicable as the Kingpin—and he quickly learns his lesson. His relationship with Mistress Death has more violent repercussions because Thanos is directly involved, showing Deadpool the danger of messing with the Mad Titan. If Thanos is a supernova with a grudge, then Deadpool is a moth that keeps flying into it while shouting ‘maximum effort!’
Comic Wade vs. Movie Wade: The Monogamy Plot Twist
Based on his comic history, Deadpool is much more promiscuous than he is portrayed in film. On screen, he is dedicated to one woman even after her death, as shown in Deadpool 2. In the comics, his sexual walkabout across the Marvel Universe led him to two love interests that he paid for pursuing, and in the process put himself on the radars of both Thanos and Kingpin in a bad way. That is a remarkable achievement, like getting banned from two separate countries for the same karaoke performance.
In 2026, Deadpool remains a cultural juggernaut, but his comic-book love life is a reminder that not every romance needs a crossover event. Sometimes it just needs a mercenary, a cosmic deity, a crime lord, and a complete inability to read the room. Deadpool may be immortal, unkillable, and endlessly quotable, but when it comes to love, he is the guy who trips over the welcome mat, knocks over the vase, and then asks if anyone saw that. And somehow, we keep watching.