A/N: So, one of my favourite Japanese Vocaloid Producers Utata-P released a new song called "A Wonderful Flag-Less World" in which basically every story has a happy ending, and it's pretty funny. Anyway, I was listening to it, and I couldn't help but want to write a bunch of SpideyPool fics about it. I mean, I can see Deadpool doing all this stuff, the bastard.
So I'll do each 'story' (there's nine of them, but they're only two lines each so…), yeah I'll put the two lines in bold italics, one at the start, one at the end. Because I'd hate to give away the punchline before the ending. :P
I got the lyrics from descentsubs youtube page, - watch?v=kf9d8fbEKd8, which has all the details, and you guys should give it a listen.
So yeah, enjoy!

"When this war is over, I'm going to marry her!" is what he said…

'I'm going to ask him out.'
[We're in a battle]
'I know. Afterwards.'
[We're in Canada.]
'I know. I'll catch a plane.'
[We're missing an arm.]
'I kn-seriously?' Deadpool cast a worried look at his arm, and then looked around, trying to locate his arm while he fought off the next wave of unoriginal and unidentifiable henchmen. 'When did that happen?'
His yellow box sighed. [Does it even matter?]
'No, I just like to keep track of these things.' He perked up. 'There it is!' He jumped over one of the men and picked it up.
"Batter's up!" he called and used his arm to knock over one of his enemies, and (as per usual with the grunts) the man collapsed and didn't move. "Who's next?" he crowed, delighted with his familiar toy.
The men all gave each other nervous looks. "Aw, guys," Deadpool smirked. "Don't worry," he waved his arm at them, "I'll go easy on you."
The men's expressions darkened at that, and they leapt toward him.

Deadpool scratched at his arm idly. He'd been able to reattach it in time, luckily. Growing new limbs was a bitch.
"Drink sir?" asked the airline hostess. Deadpool looked over the selection and frowned to himself. She smiled politely back, though he could see her confusion at the man who was completely covered, head to toe, not an inch of skin showing, despite being half an hour into the flight.
'Beer?' he asked the yellow box, which he had decided to completely trust in this new endeavour of theirs.
[Yes, turning up drunk on his door is the best way for someone to ask another person out]
Deadpool pouted. "Coke please."

Deadpool caught his reflection on the glass panes lining the window of the airport. He fixed his hoodie idly.
'Looking good.'
The yellow box was silent.

Deadpool was bored. 'Where is he?!' he complained.
[Perhaps he's not coming]
'But this is his house.'
[He could have moved out]
'And left his stuff?' Deadpool ducked under the bed and picked up a magazine. 'Left his porn?!'
[It is a conundrum]
It was a conundrum. Deadpool had been waiting patiently for three days for the lovely Spiderman to return. Three. Th-ree. 3. He needed to kill someone.
He had been so good. He'd been more patient than he'd even been.
He was going crazy.
'Okay, we need intel.'
Suddenly, the screech of metal filled the air.
[That sounds like a good place to start]

'Hey look it's Doc Ock.' Deadpool thought to himself as he jumped between the buildings to watch the unfolding drama.
Fantastic Four vs Doctor Octopus. Something was wrong with this picture.
'Isn't Ock one of Spidey's villians?' He suddenly felt his first streak of worry. If they were here…where was Spidey?
He jumped again, landing on a fire escape and made his way across to where Mr Fantastic's head was (having stretched himself in all manner of ways).
"Hey Fantastic!" Deadpool called.
The head turned to him in surprise, than annoyance. "Deadpool. What is it? We're kind of busy at the moment."
"Yeah, that's cool…um, where's Spidey though? You know, about yea high, red and blue, got a weird thing about spiders. Bit sassy."
Mr Fantastic blinked at him. "You don't know?"
"I've been out of town." The worry in his stomach twisted.
"He's with the Avengers."
Deadpool resisted the urge to sigh aloud.
"Doctor Strange asked them to help on a mission in the astral planes."
"Oh." He paused. "When will they be back?"
"A few months, that's why we're tak-"
"Months?!"
"If they come back at all," Fantastic replied, still annoyed. "There's a war going on, apparently. Which is why, as I was saying, we're looking after New York. If you could help-"
But Deadpool had already vanished.

[It isn't that long.]
'I'm already going insane from three days. I won't last months. I need to ask him out.'
[You were already insane]
'More insane then.'
His yellow box disappeared as Deadpool threw himself down onto Peter's bed.
"He'll be alright, right?" he asked the empty room.
There was no reply.

Deadpool had, with difficulty, managed to put Spiderman out of his mind. It had been two months. He had decided (with mild prompting from the yellow box) that moping around Spidey's room was not the most productive use of his time (even if it did relieve a bit of the stress).
He had taken a few jobs, and had even helped the Fantastic Four take care of New York – because there needed to be a New York for Peter to return to.
So he'd done his best. Hell, he'd even checked in on Aunt May a few times. He was on his best behaviour, because, as the yellow box delighted in telling him, he needed to get on Peter's good side, if he wanted Peter to go out with him.
Of course, no one gave Spidey that memo.
The disappearance of Wade's would-be-lover annoyed him endlessly, and he couldn't shake the fear that something was going to happen to him.
He wasn't used to feeling fear, so apparently his brain had decided to torture him with an exaggerated version of it, complete with nightmares and hallucinations.
If Peter died, Wade would resurrect him and kill him all over again.
He'd managed to get a few more details from Reed Richards, but nothing reassuring.
Something about nightmares, and undead creatures.
Deadpool wasn't used to this at all. But he'd wait, because he needed his answer. He'd made up his mind. He was going to ask out Peter Benjamin Parker, even if it killed him.

Wade knocked on the door, humming to himself. He had had a good night sleep for once. He juggled two shopping bags.
"Come in," called May. This was part of his 'getting on Spidey's good side' plan, doing the shopping for her.
Deadpool balanced the bags and opened the door. He stumbled through the house to the kitchen, placing the bags on the counter, and grinning up at May.
… and Peter.
"Wade?!" Peter exclaimed.
"Peter!" Wade replied, just as shocked. "You're back."
"You're in my house!"
May hit him on the arm, scoldingly. "Wade has been looking after me while you've been gone." She shot him a look. "Though I am quite capable by myself."
Wade shot her a winning smile, then looked nervously at Spidey. He wouldn't kick him out, right? He was being a good guy.
Peter just sighed and sat down at the table. May patted his head absently, then left the room.
There was a silence.
"Um…" Wade began. "So…is the fighting over?"
Peter sighed again. "Yeah. For now."
Wade grinned and crossed the room to take the seat next to him. "Great! Let's celebrate. Dinner?"
He felt the breath go out of him. He'd planned how this would go for so long, but it had normally involved a more romantic setting, like his bedroom, or an alleyway. And a lot more rambling. He had moved too fast, he was supposed to do a speech, or-
"Sure," Peter said, then looked surprised at himself. He shrugged. "But next week. I'm exhausted."
Wade jumped up. "Okay! Yes! Rest! I'll be back! Next week!" He wasn't quite sure why he was shouting, but couldn't stop himself. He backed out of the room. "See you Petey."
He swore he heard a tired chuckle follow him out.

…and when he came back, they married without incident…

A/n: Yeah, so that's my first attempt. I don't know, I'll probably do it better in the later ones, but this one was fun to write. Thanks for reading. :)