A/n: Age up! He's sixteen in this.
"You're actually going to do it? You're going to ask her out?"
"That's what I've been trying to tell you for the past five minutes, Sonic." A pause.
"Oh. Sorry." Sonic shook himself off, still grinning. "Look at you, all grown up and asking his childhood crush out." Tails sighed, pressing a hand to his face. "Are you going to take her on a spooky date? Since you're too old for trick-or-treating and such."
"I mean, that was the plan," Tails said. "I love you and all, Sonic, but could you do me just one favor today?"
"Of course! Anything for my best bud's first date!"
"Please don't interfere. I've been working up the guts and I want to be able to do this myself, and do it properly. She deserves that much." Sonic set his hand on the fox's shoulder.
"I promise, I swear, that I will stay out of your way," he said, pressing a hand over his heart. "I know you've been preparing for this, so I'll leave you to it." He took a breath and Tails braced himself. "On one condition."
"You just have to-"
"I know what I'm doing-"
"Just don't chicken out or call squirrel!" Sonic shouted over Tails' protests. "Take it from someone who chickens out every time I try and ask a girl I really like out."
"I'm not going to chicken out," Tails promised. He backed towards the door. "I will see you after I ask her out!"
"Love you, bro! You can do this!" The door closed and Tails was on his way to do a seemingly impossible task.
"Tails! Happy Halloween!" The fox smiled widely as (Y/n) enveloped him in a tight embrace. "So, I have a few ideas on how we can spend the holiday, but since this will be our first year not trick-or-treating, I'm not exactly sure what to do in the afternoon when the little kiddies start coming by. Ma says she's got it handled, but I wanted to try-"
"(Y/n)," Tails said, placing his hands on her shoulders. Her mouth shut with a soft clack, and she stared at him intently. "Maybe tonight, we could-"
"Tails!" (Y/n)'s younger sibling rammed into Tails' stomach, knocking the breath out of him. "Look, look, look! I'm being Sonic for Halloween! One of my friends dressed up as you! We're going trick-or-treating together, and you should come with us!"
"We're a little young to be chaperones," (Y/n) said, ruffling her sibling's temporary blue hair. "And a little old to be trick-or-treating. I think Pa said he was going with you, right?"
"Yeah, but I bet we'd get a lot more candy if Tails came with us!" She laughed.
"Maybe, but he's busy, and so am I, so you're going to have to settle for the same amount of candy every other kid gets." She nudged her sibling away from the fox. "Now hurry along." He nodded, skipping away with a cheery wave to Tails. She turned back to him. "Okay, so the first stop was a haunted house because, well, I've always wanted to try one, and-"
"That sounds great," Tails said, wrapping an arm around her shoulders. "Let's go get terrified." And then after that, I'll ask her out.
The haunted house she'd chosen was terrifying. After the first jump scare, (Y/n) spent the rest of the haunted house with her face buried in Tails' shoulder, and he had a sneaking suspicion that the actors were trying extra hard to scare them because they were heroes.
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Sonic Boys x Reader One-ShotsFanfiction
Oh no. I did it again. Got into another fandom. Welp, we're here now, and I've got ideas. Requests are strict as usual. But at the moment, they're closed.