A pizza guy named Jeremy tries to deliver a pizza to a customer named Merchant. Jeremy's thin, pale, and awkward. Merchant is a meathead and insists that he didn't order any pizza. Jeremy, in turn, insists that somebody made the call.
Deadpool—or, since he's not Deadpool yet, Wade Wilson—suddenly walks into the living room and says it was him. Merchant is understandably unnerved by the fact that some pizza-loving rando was hiding in his house.
Wade's packing a gun and a giant, serrated knife. It turns out he's here for Jeremy, who's been stalking a girl named Meghan. Wade's a mercenary, which means he'll fight or, in this case, intimidate a nerdy pizza guy, if the price is right.
After Wade scares the heck out of Jeremy and threatens his life, Jeremy insists that he'll leave Meghan alone. Wade leaves. With his pineapple and olive pizza. Gross.
Wade finds Meghan at a skate park. He drops the pizza and a handful of Polaroids of Jeremy—gun to his head and holding a sign that says "I'm sorry"—at Meghan's feet. Wade tells her that Jeremy won't be bothering her anymore, and she says that Wade's her hero. "That I ain't," he counters as he walks away.
Wade heads over to Sister Margaret's School for Wayward Girls. It's a grimy bar. Or, as Wade puts it, "It's like a job fair for mercenaries."
He returns a gold card with Jeremy the pizza guy's name on it to the bartender, Weasel. He also tells Weasel to let Meghan keep her money. Aw. What a softie.
Next, Wade orders a drink and sends it over to a big, burly dude named Buck. He tells the waitress to tell Buck that it's from another big, burly dude named Boothe. Weasel isn't happy.
Buck and Boothe fight. Barstools are thrown. Weasel's really not happy. Boothe gets knocked out. Weasel confirms that he's still breathing, and everybody in the bar is audibly bummed.
Then we find out why: They have a dead pool. Everybody bets on who they think is going to die next. Wade's money was on Boothe; that's why he sent the drink that started the fight. Weasel had Wade. Wade's offended.
Weasel apologizes and explains that he just wanted to win some money. He never wins anything. Womp womp.
Wade's not exactly moved by this explanation. He buys the whole bar a round of drinks—although it seems like he might be making Weasel buy them.
Just then, Vanessa approaches. Wade thinks she's gorgeous. Buck says he'd hit that and taps her on the butt. Wade starts to chew Buck out, but Vanessa grabs Buck in a, uh, very sensitive place. He apologizes immediately. Clearly, she can take care of herself.
Wade's impressed. Then he finds out Vanessa's a prostitute. He asks her if she had a rough childhood, and they try to one-up each other with just how terrible their upbringings were. His bedroom was a closet. Yeah, well, hers was a dishwasher box. In other words, they totally hit it off—albeit in their very weird, very own way that involves competitive suffering.
Wade buys 48 minutes of Vanessa's time for $275. Cut to…Skee-ball. He wants to get to know the real her. Also, he's awesome at Skee-ball. After some light, pre-game trash talk, he chucks a ball overhand into one of the holes.
Cut to Wade and Vanessa at the rewards counter. He uses his armful of tickets to get a pricey (by arcade ticket standards) Voltron ring. She gets an eraser.
His 48 minutes are up. Wade asks what he can get for his Voltron ring. Three minutes, Vanessa says in mock admiration of his rad robot ring.
Cut to Wade and Vanessa having sex. They continue having sex through a holiday-based montage that spans from Valentine's Day to Thanksgiving, when Wade tells Vanessa that he loves her. Well, that's one way to advance the story.
It's Christmas. Wade and Vanessa are lounging around the apartment. He tells her that they're so good together because her type of crazy matches his type of crazy. We're inclined to agree. Then he proposes with a ring pop. She says yes.
Wade's ecstatic. Vanessa starts making Star Wars jokes, and Wade's so happy that he says it's like he made her in a computer. He takes off his clothes and on his way back to bed he passes out.
Cut to a doctor's office. Wade has late stage cancer. Oof.
While Vanessa starts trying to formulate Plan A, Plan B, and so on with the doctor, Wade stares at her, memorizing her face.
Cut back to Deadpool with the thug-kebab—you know, the dude he had skewered on his swords when this whole flashback started. Time unfreezes, and Deadpool finishes the skewering. Now, where can he find Francis, he wonders.
Suddenly, a helmeted rider that must be Francis revs the engine on his bike and tries to flee. Deadpool deftly throws one of his swords through Francis's front tire, bringing him down. Then Deadpool starts exacting his revenge, savagely beating Francis up, calling the play-by-play like a sportscaster. At one point, he hits him so hard his helmet flies off.
Finally, Deadpool runs Francis through with a sword, impaling him on the wall of the overpass. He takes off his mask to show Francis just who's been wailing on him. Francis laughs.
Deadpool tells Francis that he needs to undo what he did to him, i.e., making him look like he was bit by a radioactive Shar-Pei puppy. Francis says Deadpool should thank him; it looks like he made Deadpool immortal. Yes, it does kind of look that way.
Deadpool raises his fist once more, and—clang!—he hits Colossus who's standing behind him.
Colossus picks up Deadpool by the arm and flings him out of the way like a rag doll.