The First Date

Friday had finally arrived. Winn and Lena had agreed to a great restaurant downtown for 8:00. Winn showed up ten minutes early. He went inside and was seated at their table. A waitress handed him a menu and asked if he wanted anything at which point he said he was waiting for someone. Ten minutes past and it was now 8. Lena still wasn't there. Winn decided to ignore this and looked over the menu. He also browsed his phone for a bit. Another fifteen minutes had passed and he began to get nervous. What if something happened to her? Or what if she just changed her mind. Then, as he looked up at the door he saw Lena walking in searching for him. He felt relieved .

"I am so sorry I'm late" she said, taking off her jacket and sitting down. "I came straight from the office. I had some last minute things to take care of and traffic was worse than usual."

"It's fine" he reassured her. "But to be honest, I thought you bailed. Or got caught up with work."

"I'm so sorry. I should've texted you but i figured I'd just be a few minutes late and I was on my phone dealing with work" she replied guiltily.

Winn smiled and just shook his head, "It's fine I understand. You're CEO of a big company. I'm just glad you're here."

Lena smiled back. "I am too."

Winn finally looked at what she was wearing. Lena wore a body hugging red dress. It was a V-neck with a little bit of cleavage showing. She also wore her hair down and had on red lipstick, like she did the night she saw Winn in the bar. "You look absolutely stunning," he said with bright eyes. "I don't think I've ever seen a more beautiful woman than you tonight." As he said that he started to stutter a little nervously. Maybe he was trying to hard.

Lena blushed, flattered by his compliment. "Thank you. You clean up pretty well yourself, you know."

"I try on special occasions," he told her, making her just roll her eyes with amusement. "Well now that you're here if it's alright I'll call the waiter over so we can order our food and a bottle of red wine."

"Sounds good to me."

The waiter came over and took their orders. The two of them talked and sipped their wine until their food came.

"You know I can't even remember the last time I went on a first date."

"Oh? Why not?", said Lena.

"I guess I've been really busy lately with my job and I haven't had time to meet new people. I also don't think anyone was too interested" Winn replied shyly.

"Well i can understand being busy. Ever since I took over L-Corp free time has been nonexistent. Plus, I don't think people are too keen on dating Lex Luthor's sister" she admitted solemnly.

"That's ridiculous. Anyone who can't see past your brother's mistakes to get to know you is a fool. You're amazing and any guy would be lucky to go on a date with you. I know I am. Hopefully I get to take you on more." he told her softly.

Lena smiled brightly at him. "I'd like that very much. Thank you, Winn"

"You don't have to thank me, I meant what i said." Winn then decided to grab her hand across the table. Lena squeezed his hand gently in affirmation.

Lena hadn't felt like this in a long time about someone. And they'd only just met. They're still getting to know each other. This should scare her and it does, but she liked it.

Shortly after this their food came. They ate in relative silence, not feeling awkward with each other anymore. Lena still wanted to get to know him so she started up conversation a short while later.

"So, tell me something about yourself"

Winn looked up from his plate, " Uh well what would you like to know"

"Favorite color for starters."

"Blue. And you"

"Red." Winn smirked at her reply as he once again looked over Lena in her red dress.

"Well it does look good on you."

Lena smiled. "Favorite movie?"

"The Empire Strikes Back"

"So you're a huge fan of the original trilogy I presume."

"Of course. Don't tell me you like the prequels more."

Lena looked mocked offended as she replied, "who in their right mind would like the prequel trilogy more. I did like the The Force Awakens though. I can't wait for Episode 8"

"A woman after my own heart." Lena blushed after he said this.

They were followed by silence for awhile before the waiter came back asking for desert. They decided to share a slice of tiramisu.

Lena decided to kickstart conversation again. "So where exactly do you work again?"

"I'm an FBI agent."

"Oh interesting. Is that how you know Kara, because you work with her sister?"

"Actually I knew Kara first. I used to work at Catco in the IT department."

"Really, what an interesting job switch. How did that happen?"

"It happened shortly after the alien invasion last year. I ended up helping the FBI with some tech support so they could assist Supergirl. After the attacks, I was asked if I wanted to stay on and I thought why not."

"That's amazing. So you provide tech support. Are you also a field agent?"

"Definitely not a field agent. I prefer never going into the field. I'm not trained for it. Besides I'm more equipped to do tech support. I only really go into the field if certain missions require me being onsite to run support."

"Well i'm not gonna lie, that gives me a bit of relief. I won't have to worry about you being shot at all the time."

"I'd be fine. Supergirl wouldn't let anything to me."

"Supergirl works for the FBI?" Lena said incredulously.

"No no of course not-"

"Winn relax I won't say anything." Lena cut him off.

"Sorry if I freaked out i just don't think I was supposed to actually say anything? I guess you could say a group of us assists Supergirl when necessary with things like aliens and what not. She can handle robberies and petty crimes on her own."

Lena smiled, "I get that. And don't worry I won't say anything. That is cool you get to work with her though. You're really making a difference, making this city a better place."

Winn brushed his head, "Yea i'd like to think so."

The two of them stared at each other again and went back to eating their dessert. Shortly after, Winn called the waiter back to pay the check so they could leave. As they walked outside they could feel the cold February air. Lena grabbed Winn's hand and laced her fingers with his. Winn turned towards Lena and they got close to each other. Soon their faces were mere inches away. Winn took the initiative and closed the gap swiftly. Their lips met in a sweet, highly anticipated kiss.

Lena savored the kiss and let it linger for awhile. His lips were soft and sweet, with the taste of the cake they just shared on his lips. Winn dropped his hands to her waist and pulled her closer. Lena wrapped her arms around his neck and opened her mouth with her tongue pleading to be with his. Winn responded fervently with his own tongue sliding into her mouth. Their tongues danced with each other not stopping until they both ran out of oxygen. Winn pulled away and caught a glimpse of Lena's lips, swollen from their kisses.

"That was nice," he whispered.

"Agreed," she replied breathily. Her arms were still wrapped around his neck keeping him close.

"It is cold though. I should get you home."

"Mr. Schott what kind of a girl do you think I am? Bringing you home on the first date." she replied mockingly.

"Well you did take me home before a date," he replied teasingly.

"Touche." she smiled back up at him.

"I simply meant I'd wait with you until a cab came. I wouldn't make assumptions just because of what happened the other night. You should know I really like you Lena and if you want to wait until we have sex again I'm fine with it. You're worth waiting for." He replied as he pulled one of her arms from his neck so he could kiss her hand.

"You're really sweet you know. And I promise I won't make you wait long I just want to get to know you more before we're intimate again. I really like you too."

Winn kissed her cheek and pulled away so he could hail a cab. Eventually, one came and he kissed her one last time before she got in.

Winn decided to walk home. He couldn't get the smile off his face as he thought of what this new thing was for the both of them.