Chapter 1: Ask her a question about yourself...
It was summer on Equestria, and everypony was filled with joy when they imagined the things they would do for their vacations, everypony had something to do, the Pegasi enjoyed the sun, the earth ponies were going to the beach and the unicorns were getting special treatment at the spa, and everypony had somepony to be with in the vacations.
Well, everypony except a colt with a brown coat and an addiction to videogames, this colt was named Button Mash, and he was lonely at the moment, he always hated school, but there was a reason he went there everyday with a smile on his face, and that reason was a filly named Sweetie Belle.
Button Mash didn't have the courage to ask her out, he didn't even know what girls liked, he always knew what to do in dating games, or in games where he had to make choices to affect the main story, but in real life he was scaredy, he always began to sweat when Sweetie Belle was nearby and some fillies at school made fun of him because he was a weird colt.
But not anymore, Button swore to make Sweetie Belle fall in love with him before the summer ended, he was tired of being the lonely colt at school, he was tired of the girls making fun of him, but most importantly, he was tired of being lonely on Hearts and Hooves day, Button Mash wouldn't let anything like that happen again.
Button was on his way home after the last day of school, and his mom probably was waiting for him to eat, but Button wouldn't eat at home, he was just going there to leave his stuff and go ask somepony for help. Button noticed that the house was lonely, something strange because when his mom leaves, she writes down a note for his son, but he didn't care for that, in fact, it was better because that way his mom wouldn't be asking him where he was going. Button went to his room, he dropped his bags, he grabbed a few bits to buy something and he went out again.
'Okay, Button, if you're going to make Sweetie Belle your very special somepony then you're going to need some help, but who will give me dating advice for free?' Button thought, kicking a can in his path. 'Maybe I can go over to Rumble's and ask him about this thing! After all, he DID end up with that orange filly, right?'. Button Mash's eyes lit up at the idea he had, then, he ran directly to the house of his friend Rumble, he was the right call, Button was sure of it.
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"Wait, you need MY help to ask Sweetie Belle out for a date?" Asked Rumble, surprised.
"Yeah, dude, I mean, how did you manage to ask that filly out? What was her name again...?" Replied Button.
"Scootaloo." Said Rumble, with an unamused expression on his face.
"Oh, yeah, that filly."
"Well, my dear Button, it's time you learn something about dating, girls normally don't care what you have to say, so you have to be as impressive as you can! Maybe you can do some awesome tricks in the air or some acrobatics on a scooter to get her to like you!" Explained Rumble, this time with a determined face.
"But I don't have a scooter, and I don't have wings either." Replied Button, bluntly.
"Oh, yeah, I forgot about that, but still, you need to be as impressive as you can! Don't waste on your time on that lovey-dovey junk! That'll just get in your way!" Said Rumble.
Button stayed quiet for a few seconds, staring at the floor with no expressions on his face before replying: "Are you sure that's the way to get her to like me?"
"Of course! When I showed Scootaloo how awesome I can be with my wings and her scooter he was drooling all over for me!" Replied Rumble.
"I think you're overdoing it."
"Of course not! Look, do you want Sweetie Belle to be yours?" Asked Rumble, putting his hoof around Button's shoulders.
"Yes!"
"Then you have to do what I said, you have to be cool no matter what, if you aren't cool enough for her, I bet she'll just go looking for someone cooler than you, you understand?"
"I think I do." Said Button.
"Great! Now I think you should find something awesome to wear (with sunglasses, just in case), and ask her a question about yourself!"
"About myself? Like what?"
"Ask her something like, 'what's your favorite thing about me?' or 'Do you want to date Ponyville's most awesome guy?' I'm sure you'll get her to like you in no time with those!"
Button looked away, this whole thing seemed wrong, Button wasn't sure if Sweetie Belle would like to date a guy who just bragged about himself? But then again, he remembered her saying that she liked cool guys in one occasion when he was spying on her.
"You know what? I'll do it! I'm going to show her that I'm the coolest guy in Ponyville!" Said Button with determination.
"Second." Replied Rumble, winking at him.
"Uh-huh, whatever you say, bud."
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It was almost night time on Ponyville, and everypony was inside their houses, except for Sweetie Belle, who ocasionally sat on a bench near the park to sing some of her favorite songs without anypony judging her, or at least that's what Button could get when he spied on her.
Speaking of him, he was wearing a black jacket and sunglasses, his mane was combed back in a cool way and he was wearing a false moustache, he liked the moustache. He noticed Sweetie Belle sitting alone on the bench ahead of him, and so he put his plan in action.
Button approached her walking slowly and cool, and he noticed Sweetie Belle had stopped singing and was looking at him in a weird way, like she didn't recognize who was she seeing, when Button reached her, he sat by her right side and smiled at her, making her blush slightly.
'Oh, brother, I can't believe this is working!' He thought.
"Button Mash? Is that you?" Said Sweetie Belle, looking at him with half closed eyes.
'Oh, no! Don't let her see me blushing! She will think I'm not cool!'
"Yes, Sweetie Belle, it's me, but you can call me Button, my dear." This last part made Sweetie's cheeks go red. 'Oh, yes, I got her now!' "Say, do you mind me being here?"
"O-of course not! We're friends, right?"
'Oh, dear Chtulu, not the friendzone! I must think of something to ask her!' Button thought, then, he remembered something Rumble said.
"Hey, what's your favorite part of my new look? Mine's my moustache!" Said Button Mash.
"Button? Are you okay? This doesn't seem like yourself." Said Sweetie Belle, she could see something wasn't right.
"Of course I'm fine! I just want you to respond my question!" Said Button, now nervous.
"Well, maybe the jacket?" Replied the filly, who was getting really uncomfortable.
"And have you noticed how incredibly big of a loser I was before? It's unreal!"
"Button, stop it, this clearly isn't you." Replied Sweetie Belle, feeling an urge to get out of there.
"Well, it's not my 'old' me, this is the new and improved me, the one who will be staying forever!"
When she heard the word 'forever', Sweetie Belle stood up, surprising Button Mash. "Button, if this is the way you're going to be from now on then I don't want any part of it, I can't believe how big of a jerk you've turned into!"
"B-b-but you haven't seen the incredible acrobatics I can do! Wait! Come back!" Button tried to convince Sweetie Belle to stay, but it was no use, Sweetie Belle was already trotting all the way back to her home, with Rarity.
Button was left heartbroken, what did he do wrong? Was it something he said? Was it something he did? He really didn't know, and the worst part was that he couldn't even ask her out, it really went bad. But it didn't matter now, because he needed to get home before his mom or he could be in great trouble if she gets there first.