A/N: This fic is an AU that is a conglomeration of all the Spider-Man movies merged with the Deadpool movies, as well as what I can remember from the comics I read as a child. ;p (P.S. I do not own these characters [they belong to Marvel and 21st Century Fox respectively]; I only own the situations they find themselves in.)

Update: Now cross-posted on AO3 and Wattpad.

PART ONE:

5 Increasingly Clichéd Meet-cutes Plus 1 Not So Cute-meet

Summary: As the title says, this is the first five times Deadpool and Spider-Man (and Wade and Peter) meet, before Peter starts thinking of them as friends, and the one time it all falls apart because Peter doesn't understand that communication is key to working relationships.

The first time they met, Peter had only been Spider-Man for about a year and a half.

He was sixteen, almost seventeen, a senior at Midtown High, and could only afford to patrol Queens between the hours of 11 PM and 4 AM because he'd had to get a part-time job. He'd gotten the job to ease Aunt May's suspicions about him being Spider-Man (recently, she'd asked him why he always came home sporting bruises in that skeptical tone she used when she wanted to interrogate him but refrained from doing so because she didn't know if she should, which made Peter realize he hadn't been as subtle as maybe he should've been). He was afraid that she'd get a heart attack if she ever found out he was fighting crime and aliens in his free time. Peter couldn't deal with her death.

Not—not after Uncle Ben…and Captain Stacey.

And G—Captain Stacey's daughter (even now, he could barely think her name before falling apart).

Their deaths were still so, so fresh in his mind.

He still felt the guilt of them every single day, unable to talk about the pain, anger, and all-around shame he felt in having had a hand in their demise with anyone, because who could, or would, understand? Not to mention the fact that he couldn't tell anyone he was Spider-Man.

He'd learned that lesson the hard way, with Harry blaming him for his father's death. He still felt horrible for being the cause of Harry taking up his father's work as the Green Goblin.

Peter still woke from his tormented nightmares covered in sweat, afraid his hands were still covered in Ben's blood. The sound of Gw—her spine breaking still echoed in his ears anytime he heard something snap. Captain Stacey's scared, imploring eyes still haunted him every time he saw a squad car or a uniform.

It was the nightmares that made Peter decide to run himself ragged with school, patrolling, and his internship at Oscorp. Keeping himself busy to the point of bone-weary exhaustion meant that he didn't have to worry about the nightmares taking his few hours of sleep away from him. It meant that his dreams couldn't torment him with his many failings as a hero (he really hated that word—preferred vigilante, actually—because he was no hero). If he kept himself busy, he could just fall into bed and pass out without worrying about reliving those nights—no muss, no fuss.

Thus, working on only two hours of sleep (he'd gotten up early to fix May breakfast before her shift at the hospital because that's what you did for people you love), six cups of coffee, four Monsters, and two Red Bulls, Spider-Man found himself swinging through the streets of New York, barely able to keep his eyes open. It was a Wednesday night, and Spider-Man had already stopped several muggings, helped a few kids get away from bullies, and even saved a poodle from a speeding cab.

Spider-Man had just handed the poodle back to its owner when his exhaustion made itself known through the fact that he failed to throw out a new strand of his very own patent-pending silk while he webbed away. He grabbed a nearby lamppost just in time to catch himself from painting the pavement with his insides. This near-death experience convinced him to find a roof to perch on, so he could listen for the crimes that would inevitably happen, rather than accidentally causing his own death by sluggish reflexes.

He blamed his sleep-deprived brain for the reason his Spidey Sense didn't alert him to the blur coming at him when he swung his body up on top of the roof of a nearby high-rise he liked to frequent, because it was right in the heart of his burrow and it had a nice overhang that kept him safe from wind and rain.

When the blur tackled him, it was like being run over by semi-truck and then body slammed into a brick wall. That brick wall resolved itself into large muscles clad in red and black spandex, wearing a panda mask reminiscent of his own, and a rough voice that sang "—like a wreeecking ball" off-key into his ears. Spider-Man who, even when surprised, never lost his balance, grabbed a strap on the man's back and tucked himself into a roll, tossing the man down on the roof and coming up on the balls of his feet. As Spider-Man backflipped himself several feet away, he shot a few wads of webbing at the man that had tackled him, sticking him to the roof by his hands and feet.

It was only then, with space between them and adrenaline coursing through Spider-Man's veins, that Spider-Man was able to take in the weapons strapped to the skintight suit of the man now stuck to the ground. There were two katanas strapped to the man's back, twin guns in holsters on the man's thick thighs, knives sticking out the top of heavy combat boots, and numerous (like so many) pouches on the man's belt and strapped to his chest. It kind of looked like he was wearing a fully functional tactical suit like the ones SWAT members wore, and that instantly put Spider-Man on the defensive because that meant the man webbed to the ground was either ready to take on a significant amount of damage or dole it out.

Spider-Man knew Deadpool by his infamous reputation as the Merc with the Mouth and had heard the many…rather gruesome stories that followed the gun for hire's name. He'd started hearing whispers of the masked man about a year after he'd taken up the Spider-Man mantle, whispers from some of the chattier criminals he'd webbed up. When he'd started digging around for information (in order to learn if he needed to watch out for the mercenary) his search lead him to the X-Men where he'd learned the red and black soldier of fortune apparently had a soft spot for the underdog—liked to help the little guy, kind of like Spider-Man himself. Plus, Logan had seemed reluctantly fond of the "nuisance that is the irritatingly chatty antihero," and Logan was rarely enthusiastic about anything besides his cigars and beer.

The rest of what Spider-Man learned about Deadpool came from the file that Iron Man had tossed his way five months ago. It'd been after the last Skrull invasion, and Tony had said, "read up on this, kid. Make sure you run the other direction and call the big boys if you ever see this guy in your burrow."

Spider-Man remembered reading from the file something about Deadpool having a phenomenal healing factor that could bring the man back from the dead, scars that covered the man's body (though to what extent, no one really knew), and that he was stronger and faster than he looked. Spider-Man also remembered being pissed off that Iron Man still treated him like a kid when he'd battled supervillains and even teamed up with the Avengers and Fantastic Four on more than one occasion. Spider-Man liked the Avengers well enough (even more so when they all went out to eat after a mission and he got free food) because it was like being part of a rather large, dysfunctional family. However, he hated being the "baby" of the group and usually chose to ignore their warnings. He only regretted that about half the time.

A sound pulled Spider-Man from his musings and it took him a minute to realize that Deadpool had been talking ever since he'd crashed into Spider-Man. It took him even longer to follow what Deadpool was saying. When he was able to tune into what Deadpool said, the lenses in his mask narrowed, because Deadpool had somehow freed his hands from the webbing and used them to express his excitement (the file didn't mention that Deadpool would be that strong).

"—and I was just tellin' Yellow that even though tacos go right through us, and it wouldn't be the first time we died on a toilet all Elvis Presley style—ah-huh, thank ya, thank ya very much!—we should stop at that lil truck we found by the park and grab a couple of 'em. Then Whitey informed us that the Skrulls smashed it when they invaded, and that ain't right, Spidey. I'm tellin' ya. But then we saw your sweet ass—I mean for reals, Baby Boy, that ass should be illegal—all thwip-thwipin' through the streets and I just had t'get an autograph on my Spidey tee." Deadpool continued, without taking a breath, "running into you just made our day, Cutie-Man. And dat ass, I swear to Thor's pretty lace panties, mm-mm-mmm. We could do so much damage to dat ass."

"Deadpool," Spider-Man said in his most Captain America Disapproving Hero Voice™ trying to ignore the flush in his cheeks at the praise of his butt, "what are you doing in New York?"

"Gasp! He knows who we are!" Deadpool slapped his hands against his cheeks, and somehow the white eyes of his mask expanded in surprise (how did he make his mask express emotions?), and…did he just…say the word gasp? "Hurry, hurry, where did we put the phone? We need to document this! Spidey knows us!"

"Answer the question Deadpool," Spider-Man said, tilting his head to the side as he heard a car alarm go off in the distance. And then he looked back at Deadpool because, what the hell? He was using the first-person plural to refer to himself. "Why are you in New York?"

"I'm layin' low, Baby Boy. Shut up, we are not singin' a Flow Rida song on our first meetin' with Spidey-babe. Any-who, Baby Boy, some big baddies got wind of my Arizona place an' shot it to hell, which would normally twix my nethers, if you get my meanin', but I'd just got back from a job and all I want is some sleep, so I'm in the big apple goin' to ground," Deadpool said as he grabbed a knife from the top of one of his boots and sliced it through the webbing that strapped him down. He stood, and Spider-Man took a step back, raising his arms in a defensive position, but Deadpool only pulled a rolled-up t-shirt from one of the many pouches on his belt, offering it to Spider-Man along with a white sharpie. "I'm your biggest fan, Webs. Can I get your autograph?"

Spider-Man was not used to people asking for his autograph, as most people in New York City didn't know how to feel about him since the Bugle kept labeling him as a menace to society, and a vigilante, at best. He was especially not used to dangerous, bulky mercenaries fangirling over him like a teenager who just saw their favorite actor take a shirt off. Spider-Man would forever blame Deadpool's knack of circumventing expectations and talking too much for just one person to follow, for the reason he took the offered shirt and sharpie without much thought.

He unrolled the small bundle and immediately thanked all the gods he knew, that he had a full faced mask that was invaluable at covering when he was scared, or blushing, as the case currently was. The shirt was black, with a cartoon version of his vigilante persona shooting a white web down at the bottom of the shirt, and the words "Spider-Man can CUM at me, anytime."

Suppressing a non-hero-like giggle, Spider-Man signed the shirt. He added a little note of his own that read: "Not until after the third date, Big Red," with a smirk, because, well, he was a teenager and even he had to admit the shirt was pretty funny, if a bit gross. He tossed the shirt and marker back to Deadpool and stepped up to the side of the building where he could hear a robbery happening a few streets over.

"No killing in my city, Red, and we won't have a problem," Spider-Man said before flipping himself off the building and swinging away to catch the robber, all to the fading lyrics of "Low" that Deadpool decided to scream-sing after him.

It would take Spider-Man another three nights, during his bimonthly fight with the Green Goblin, for him to realize that the supposedly most dangerous mercenary in the world had never once set off his Spidey Sense. Something he knew was apparently still intact (even when he was running on a weekly amount of five hours of sleep) because it alerted him that several of the pumpkin bombs that the Goblin threw his way in order to make his escape, were about to detonate and collapse an abandoned building on top of him.

This is the reason Spider-Man resigned himself to only keeping an eye on Deadpool if the man stepped out of line. Yet, he was surprised to learn that Deadpool only stayed in the city for a few more days after that first meeting and had actually refrained from killing.

Spider-Man did, however, find a badly beaten mugger the day Deadpool left, with a note stuck to her forehead that read: "One date down, two to go. Love, Big Red."

If Spider-Man kept the note, well, no one would ever know. Besides, the cartoon drawing of Spider-Man and Deadpool sitting at a candlelit table with tacos on the plates in front of them was too cute (if a bit nonproportionate) to throw away.