This is actually an original prompt inspired by the Writer's Book of Matches: 1001 Prompts to Ignite Your Fiction. The original prompt is vowing to ask someone out after having too many drinks. And in a spirit of NaNoWriMo, SpideyPool made this happen, enjoy!

I DO NOT OWN EITHER SPIDER-MAN OR DEADPOOL. BOTH ARE RESPECTIVELY OWNED BY STAN LEE AND MARVEL

WARNING: This fanfiction contains alcohol, swearing, innuendos, homoerotic situations, Wade Wilson, fourthwall breaking, pop culture referencing, gratuitous cameo of Stan Lee, and things of that nature

It all started with a few shots.

…Ok, so it was more than just a few shots.

But how can you get that buzzing feeling from only a few shots? Only a light weight pussy would be knock out cold after a second! And he's a lot of things (mainly a dick) but he ain't no light weight pussy.

(…pfft, sex jokes).

Anyway, this is where Wade W. Wilson was currently at the moment. Drinking to the point of destroying his liver at Saint Margret's Home for Wayward Girls.

"Maybe you have enough." Weasel commented after staring at what seemed to be the closest thing to a glass pyramid.

Maybe YOU should shut up!

Don't say that!

What?!

If you make us say that, he wouldn't give us the good stuff forever. And we just got started with this short story!

SHIT! We can't fuck this up early! Come on! Say something witty but not enough to get our short story be cut…short! And save our drinking privileges!

"Maybe YOU have enough."

Nailed it.

Classy…

"Real mature, Wade." Weasel simply deadpanned before cleaning another glass. "So, what's up with you lately?"

"Nothing much…" Wade managed to speak out. Maybe it was the shots, but he was feeling something. And it's not in his pants. "Knocked some heads, had some pity sex, knocked some more heads, TOOK a dick and shoved it back some guy's throat before taking his head, the writer can't come up a believable reason that would also done justice to my comics and movie cause her reality is being a bitch. And also, my hand was tired along with Hot Jizz."

Duuuuude. Don't mention our alone time! Hot Jizz is sensitive about that! He's such a sweet little unicorn.

I think it was the alcohol kicking in…

No way, we don't sound drunk! Yet!

"Yeah, I get it…" Weasel nodded, just casually cleaning another glass. "Sometimes I wish I have a girlfriend too." Then he sigh as he thought about it. "And it's not just a one-night stand."

"I can place my dick in anyone and anyTHING." Wade declared before downing another shot.

"Ok, Dude, first of all, you're gonna have alcohol poisoning at this rate." Weasel pointed out. "Second, even if that's true, I highly doubt that you would be sober enough to land yourself a date."

Wade glared up at his friend, or at least tried to. Maybe it was the buzz kicking in. Why was the room spinning?

"Is that a glove bitch-slap that you just gave me?"

"If you meant challenge, then yes. Yes I did."

Oh. It is ON like Donkey Kong!

We need to know what the wager is first.

"Okie dokie Loki~" Wade sang out before downing another shot that somehow magically appeared. (Maybe Weasel is Loki? He doesn't look like Tom Hiddelston. Looked more like T.J. Miller…didn't he ride dragons and somehow got a battle suit with a marshmallow balloon?). He let out a satisfied sigh as he added the now empty glass to the growing pyramid. "Name it."

"You manage to ask the next person who walk through that door out on a date, possibly get a phone number, and I might let you have the good shit for free for the entire year."

Sounds reasonable enough.

"And if I fuck up?"

Then came what Wade could describe a shit eating grin as the light of the bar lit up Weasel's glasses in a menacing manner, just like what he have seen in anime. And no it wasn't the ones with tentacle porn. (Plenty of huge boobies though).

"You pay the tab."

Well? What do you think? Should we do it?

Fuck the Hell yes, we should! Free booze for a year yo!

As Wade weighed his options, he had come to a conclusion before taking another swig of his drink and let out a satisfied sigh.

"Challenge accepted!" He announced as he slammed the glass to the counter, making an effective clank.

"Good, cause here comes destiny."

Beyoncé? Wade narrowed his eyes before turning around in time to see the door opened, revealing what he can only describe as sex on legs.

It could be that delayed buzzing feel-though the room was kinda spinning a bit- but there stood by the door was a man, probably late teens to early twenties due to how baby-faced he looked. His outfit left little to the imagination but Wade could see that he had a slim physique like a gymnast or an acrobat (wait, are they actually the same thing?) and have legs that could go for miles. That smooth, perfect skin that was begging to be kissed and be peppered with love bites, crazy brown hair that is so goddamned fluffy and defiant against management, and those pretty hazel eyes that he could practically drown himself in.

And with a bar filled with thugs, ruffians, psychos and tax collectors, he was like an angel just wandered out of Heaven and into the Devil's nest.

God, that sounded like out of a terrible fanfiction written by a thirteen year old…I fear for the literature of humanity.

Forget that! Why are we stalling?! Get your ass over there before any of these asshats make a move on him!

It was easier said than done, but he somehow managed to maneuver himself off of the barstool and made the beeline towards the beauty, who seemed to be looking around the premise before taking note of him.

"Hey~, Baby Boy."

Yeah, that's an icebreaker.

Baby Boy (he's gonna call him that for now) blinked rapidly a few times before taking a notice of Wade, looking a bit like a deer that was about to run over by a semi-truck. He's not that scary, is he?

"Can…I help you?" he asked.

Did he jumped the gun too soon with the pet name? Is it the bloodshot eyes? Does his face make him look like Freddy Kruger's redheaded stepchild?! Fuck it, the ball was already rolling and time to make this ship happen while being a non-shitface.

"I was wonderin' if ya do a favor for me~" God, why did the buzz picked this moment to reveal itself?! Now he sounded drunk! And crazy! …Er!

"Ok?" Baby Boy's response somehow came out like a question and wait, did he just backed up a bit? He knew it! He did jumped the gun with the pet name!

We're passed at the point of no return, we can't abort! Repeat, we cannot abort!

For God's sake, Weasel is going to win this and will NOT allow us to live it down!

"Would ya do the honor of going out with me?" Wade was surprised that his words managed to come out clearly, even if he was slurring a bit. God, he hoped that he wasn't smiling like he was some crazy person. Even if he didn't win the bet, he could at least get a number from Baby Boy. Whether it was a real or a fake number.

Luckily for him, Baby Boy didn't do anything like make up some lame excuse before exiting out of the building and never be seen again (along with his free booze privilege). Instead he cocked his head to the side-seriously, with those eyes, he could place all puppies in the world to shame- and rose an eyebrow.

"And why would you go on a date with me after knowing each other for a few seconds? I literally just walked through the door."

Cause it's instant true love?

That is Disney logic. It doesn't work like that in the real world.

Works for Stan the Man!

He's the Almighty All-Father. He doesn't count.

"Cause you're a nice leg of lamb, with those pretty doe eyes."

And that was God's honest truth. He's good enough to eat and he had pretty eyes that could make your knees buckle. That and it was the first thing that came to his mind.

Baby Boy seemed to be thinking over on what he said for a bit, while staring at him up and down. Well, he wasn't really the most well-dressed person but hey, in a bar like this, formal clothing can suck ass. Besides, there was this one time a patron came in dressed in a gimp outfit and no one even batted an eye. He seemed to have relaxed a bit before staring up at him straight in the eye and gave him what he dubbed as the cutest smile that he had ever seen.

"Sure, why not?"

Wade would have done a flip on this, but he was nearing to blacking out. Besides, face planting upon the floor and making himself a complete ass. Baby Boy took the moment to pull out a pen from his pocket (God, those pants…so tight! How did he get in them?!) and took his hand to scribble something down, most likely his number. All the while Wade took note on how soft and warm Baby Boy's hand was against his skin.

Please let it be his real number…

"There, my cellphone number." Baby Boy told him, still smiling. It could be the shots, but somehow it gave him a minor superpower to know a real smile from a fake. And that is the most realist real smile that he had ever seen. And it was sooooo pretty…

"And speaking of cellphones…I think I left mine…oh there it is!"

Wade could feel his heart letting out a thump in his chest as he watched him head over to one of the tables which was found by a Hell's Angel wannabe who held up the cellphone. Feeling his inner Marine flaring up, he was ready to make a move to defend his Baby Boy's honor. Shit-faced or not. No one messes with his Baby Boy while Wade Wilson is around! But before he could even make a step, Baby Boy thanked him and head back to the door on his merry way. Not before giving him a slight wink and a smile.

As soon as Baby Boy left the building, a dopey smile actually grew on Wade's face as he managed to make his way back to his seat by the bar and grinned up at Weasel in what seemed to be triumphant while holding up his hand with pride.

"Suck. On. That."

However Weasel doesn't seem to be distressed at this, and the evidence of that was a risen eyebrow behind his glasses.

"Unless that is a fake number that he gave ya, and he's only being nice."

Wade rolled his eyes, along with his head, at his logic.

"Yer jus' jealous cuz I came across a talllllll drink of water!" Then he smirked as he leaned against the counter. "An' I'm a thirsty Marine."

"So says the guy who can drink an ocean of this stuff." Weasel deadpanned as he added another empty shot glass to the growing tower. "So…riddle me this: how long will it take for you to black out?"

For some odd reason (maybe not), Wade suddenly burst out in drunken laughter and pounded upon the countertop of the bar.

"I have no idea, you cray-cray…" Then he quickly stopped before finally fell face flat upon the countertop with a thud, the glass pyramid shook a bit as a result but managed to stay standing. All the while Weasel just propped up on his chin with one hand as he took a look at his watch.

"Just 15 seconds to hold out. Not bad."

Now the new question is, how bad will the hangover be tomorrow?