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."

"Wait, you've never been on a date before? How is that even possible." She was shocked.

"I wasn't the most popular or best looking in school." You said sheepishly.

"Even if that were true, look at you now! You're beautiful, super smart, and a total badass! How has no one snatched you up yet?" She raised an eyebrow.

"Thanks!" You laughed, "just lucky I guess."

"Hmm, well, just you wait. It'll happen." She assured.

"Yeah, maybe someday." You gave a small smile, "But in the meantime, I should probably get back to work."

You were kind of embarrassed having never been on a date at your age. You supposed that you could've asked someone out yourself, but you were far too shy for that. So, despite being bored out of your mind, you lied about work to make the now awkward conversation end.

"Ok, well I'll see you later then." She nodded.

Winn's pov

Alex made her way back to Winn, who was beyond not happy that she did that.

"So...?" Winn held his breath.

"Do you have that trace yet?" She had to multitask.

"Yeah, here." He handed her an address.

"Thanks. So, she's never been on a date before. Like, ever."

"Great. No pressure or anything." He mumbled.

"You'll be fine. Just be yourself." She gave him a smile before taking a look at the paper he gave her. "Anyways, I gotta go."

"Hey, Winn." James said with a confused grin as Winn walked into his office at CatCo. "What's up? I wasn't expecting you."

"James, you're a stud muffin, or whatever-"

"I'm sorry?" James scrunched up his face in confusion.

"I mean, women love you."

"I guess?"

"So, you can help me." He said matter-of-factly.

"Ok, now I see where you're going with this." His friend nodded. "What can I help you with."

"Well, I was going to ask Y/N out, but I didn't know how, and then I found out she's never been a date before."

"Wait, really?"

"I know, how is that even possible?" His expression was that of shock and confusion, "Anyways, I don't know what I'm doing here! It has to be special!"

"What, like a flash mob or promposal?" James joked.

"The flash mob wouldn't work useless I catch her outside of the DEO. And promposals usually consists of banners, which probably wouldn't be the best idea, either. Maybe I could sing to her or get a cookie cake with 'will you go out with me' written on it? I don't know, none of these ideas sounds very good. What do you think?" Winn contemplated all of the possibilities.

"Wow, you are really overthinking this, man." The taller man stated. "I say just keep it simple and ask her straight out."

"Hmm, I don't know. But thanks." Winn smiled before leaving his friend's office with a small wave.

As he made his way to the elevator, he saw Kara walking through the office with a small pile of paperwork.

"Kara, Kara, Kara!" Winn quickly got her attention.

"Hey, Winn! What are you doing here?" She looked perplexed.

"I desperately need advice!" He groaned.

"Well, you've come to the right girl!" She nodded enthusiastically.

"So, I want to ask Y/N out but it's her first date and I need to figure out a special way to ask her." Winn practically said in one breath.

"Well, first thing's first, you need to calm down and try to take the pressure off of yourself." She waited for him to take a deep breath before continuing. "You just have to be yourself and-"

"You're just as bad as Alex and James!" He whined.

"Wait, you went to them first? I thought I was supposed to be your best friend." Winn was too wrapped up in his own nerves to realize she was joking.

"You are, but James is my best guy friend and he has more experience in the lady department. And Alex is kinda like my sister now, too, and when did that even happen? When did we cross the threshold from friends to siblings? I don't even know if Y/N will say yes-" He rambled on.

"Winn, listen to me." Kara put her stack of papers on a nearby desk before taking him by the shoulders. "How about instead of focusing on making the asking part special, you focus on making the date special?"

"Oh my, God..." An idea slowly dawned on him, "Kara, you're a genius!"

"Oh, um, thank you!" She grinned.

"No, thank you! I gotta go!" Winn said as he rushed off.

Your pov

You stared at the clock in the corner of your computer screen, just waiting until you could finally go home. The day just seemed to drag on and on and on. The highlight of your day was your short conversation with Alex a few hours earlier. You could feel your brain turn to mush as your mind began to wander.

You were so relieved when Winn showed up at your desk. You would usually show up at each other's stations at the end of the night and talk about your days. It was like a little tradition between you two. You couldn't wait to hear about his day; it was bound to be more interesting than yours.

"Thank goodness you're here! Please tell me your day didn't suck nearly as badly as mine!" You put your hand on his arm.

"You wanna go out with me?" He asked calmly.

"I'm sorry?" You weren't sure if you heard him correctly.

"Would you like to go out with me?" He reiterated.

"Oh," you sighed, "I see what's happening. Alex told you I've never been on a date before, so now you think you're doing me a favor-"

"Oh, no! That's not- I'm not-" He suddenly became a bundle of nerves. "Alex talked to you about that because she saw how nervous I was about asking you out."

"Wait, really?" You smiled in disbelief.

"Well...yeah." He rubbed the back of his neck. "I mean, I really like you and I think you like me. Unless I read something really wrong."

"I-I'd love to!" You laughed, trying to hide how excited you truly were.

"Great! So, tomorrow then? Eight o'clock?" He beamed.

"Yeah! That's perfect!"

The next day came and went. The two of you spent the whole day smiling and making eyes at each other from across the control room. The closer you got to the end of your shift, the faster your heart raced. You were never more excited to leave work then you were on this day. You were ecstatic to race home and get ready.

You were just putting the finishing touches on your hair when you heard a knock at your door. You rushed over immediately but composed yourself before opening it. Your face lit up when you saw Winn standing there with a bouquet of roses.

"You look amazing!" He breathed out.

"Thank you! You're not so bad yourself." You giggled, taking the roses from him and gesturing for him to come in. "These are beautiful! Thank you."

"Well, I figured that with this being your first date and all, you should get all of the first date perks."

"That is ridiculously sweet." You laughed.

"Not nearly as sweet as you."

"And that is ridiculously corny." You both chuckled.

"So, where are we going?" You asked as you found a vase for your roses.

"That is a surprise." He winked.

You were a little confused when you arrived at the park around the corner from your place. You trusted Winn, however, so you just rolled with the punches. You took a moonlit stroll through the park, hand-in-hand, while chatting about nothing. You turned into a small clearing between a couple of trees and were taken aback by what you saw. There were activity stations set up in the grass, lit by a couple of studio lights hooked up to a generator.

"What is all of this?" You furrowed your brow.

"I wanted you to experience all of the typical first date activities you've missed out on." His voice was tender and sincere.

"Winn, you did this?"

"I mean, I had some help from my friends." He shrugged.

You were at a loss for words.

"Here, let me give you the grand tour. So, over here we have a candlelit dinner for two and here we have our own private movie theater with the finest selection of classic date movies." He motioned towards a table and chairs covered in a white cloth, candles, and two plates covered by metal domes. Then he gestured to a screen and projector that was hooked up to a laptop with a pile of dvds laying beside it. There was also a blanket laid in the grass in front of it.

"Then over here is a classic carnival game, bowling, and ice skating courtesy of Supergirl's freeze-breath." He pointed to the homemade ring toss booth, a children's bowling set on top of a long sheet of plywood, and a large inflatable pool with water that was frozen solid, a couple of pairs of skates sitting beside it.

"I was thinking dinner first and then skating before the ice melts. What do you think?"

"Oh my..." You clasped your hands over your mouth. "This is incredible!"

"Well, that's because I think you're incredible." He smiled at the ground as his cheeks turned pink.

"Thank you. This is better than I could've ever imagined." You were absolutely touched.

"Anytime." His eyes smiled. "So, where would you like to start?"

"The goodnight kiss?" You smirked coyly.

"Great choice." He leaned in and gently pressed his lips against yours, your arms wrapping around each other.