Something Special

Winn sat at his computer at the DEO, fidgeting with a toy that he kept on his desk. He stared off into space as he contemplated asking you out. It wasn't so much whether to ask you out or not, but rather how to ask you out. He always got nervous talking to beautiful women, but with you, it was worse. You were really special to him and therefore needed to be asked out in a special way. He couldn't just ask you.

"Earth to Winn!" Alex waved a hand in front of his face.

"What? Oh hey, Alex." He shook his head. "What can I do for you?"

"Can you trace this for me?" She handed him a piece of paper with something written on it.

"Sure can!" He took it from her and started running a trace on his computer.

"So, what's on your mind?"

"What do you mean?"

"You were totally zoning out a minute ago."

"Oh, right." He looked around and changed to a whisper, "See, I'm trying to figure out how to ask Y/N out."

Alex bent down to his level and whispered back, "Why don't you just ask?"

"Because..." Winn searched for a reason that didn't sound dumb, "because it has to be special. Plus, she's my friend and I don't exactly have a great track record with liking friends."

"I remember."

"I mean, I think she actually likes me, so that's an improvement over last time." He shrugged. "So, if I'm going to fail, I might as well fail spectacularly, right? Or is that just really dumb?"

"I think you should just be yourself." She clasped his shoulder. "But if you want, I can go ask her about it."

"Oh no! No, no!"

"I won't mention you, don't worry." Alex said before walking over to you, causing Winn to bury his face in his hands.

Your pov

You sat at your station, bored out of your mind. It was a quiet day for alien activity, which was good, you supposed, but it was boring as heck. You were practically giddy when you saw Alex coming over to you.

"Hey, Y/N."

"Hey, Alex! How's it going?" You hoped she had anything for you to do.

"It's going." She nodded.

"Do you have something for me?" You tried not to sound eager.

"Nope, just thought I'd come and say 'hi.'"

"Oh, well 'hi.'" You grinned.

"So, have you seen the new trailer for [movie] yet?"

"Yes, it looks amazing!"

"I can't wait for it to come out! I'm going to take Maggie to go see it." She gushed. "You know my girlfriend, Maggie, right?"

"Yeah, we met briefly last time she was here."

"Hey, speaking off, I was actually hoping you could give me some advice." She segued into the real reason she was there.

"Oh, um, I'm not sure I'd be the best candidate for that, but okay." You nodded.

"Why do you think that?" She was curious.

"Well, dating's never really been... a thing for me." You got quieter as you spoke.

"Y/n, when was the last time you went on a date?" Alex tried to sound casual.

"Um, let's see, today is Thursday, so... never."