A/N: Holy crazy response, Batman! Thank you all so much for your kind words and for alerting/adding this to your favorites. I'm astounded and so happy you guys are loving this just as much as I am!
I'm also happy that I wasn't the only on surprised by Damon's reaction in the last chapter. I did NOT expect that at all when I sat down to write it, but Damon had other ideas. Turns out, that's my favorite chapter.
This is a long fun chapter and I hope you enjoy Damon and Elena's first date...
April 2006
Sometimes she wondered if she'd be better off dropping out of school and becoming a full time waitress. At least she knew she was good at it. And she had impeccable patients when it came to customers that were way too forward with her. She wasn't sure if she'd be good in the medical field. Sure, she loved it and became extra committed to that as a profession after she lost her parents, but it was a scary and unpredictable field.
She finished up her regular routine before heading out for her early evening shift at work. It was the first time in ages she had the early shift on a Friday night and she was very much looking forward to a quiet night in her sweats watching movies and maybe reading ahead in her classes.
She grabbed all her purse and had her heels in hand to put on once she arrived at work, and opened her front door. She was shocked to see a pair of wide blue eyes staring at her.
"What are you doing here?" She asked in a surprised voice. Her heart immediately picked up its pace in response to his presence.
He stood frozen with his fist raised and ready to knock. Once she spoke he was pulled from his state and immediately placed his arm by his side. A look of embarrassment crossed his features, but was quickly masked when he put his smirk firmly in place.
"Go out with me tonight," he said.
"No," she said without hesitation and pushed past him to lock her apartment door. She tried to push aside her body's reaction to him and was barely successful.
"Wait, what?" He said surprised as he followed her down the stairs, "Why not?"
"Well first, you didn't ask," she started, "And second, I have to work."
"Ok," he sighed, "Will you go out with me after you get off work?"
"No," she repeated. She smiled a little when she could hear him huffing behind her.
"Why not?" He asked again once they got outside, he grabbed her arm gently to stop her from walking away from him.
"Because I don't want to," she said simply, "I have to get to work."
She shrugged him off and walked away, pleased at the look of surprise that crossed his face.
A half hour later she was changing her shoes and clocking in for the evening. She actually enjoyed waitressing, unlike most of the people she worked with. She was good at it. She always made her customers feel like friends, which was not easy in the fancy restaurants of the Upper East Side. She always made it out with some hefty tips that made even the worst of shifts worth it.
Tonight, the time flew. The early evening shift was always busier than the closing shifts. She was enjoying herself being so busy.
"Elena!" Came the hostess, Anna's, voice, "You have the hottest guy who requested to be seated in your section."
"He requested to sit in my section?" Elena asked surprised. That never happened.
Anna pointed him out and Elena found the raven-haired man she was pointing to. Even seeing the back of his head, she knew who it was.
"What do you want, Damon?" She hissed at him after she marched straight over.
"Is that how you greet all your customers? We may have to work on that," he smirked.
She was infuriated. How could someone so good looking be so utterly obnoxious?
"Damon," she warned.
"Ok, ok, put the claws away, kitten," he said in mock surrender with his hands in the air, "I just came here to see what time you got off so I could ask you to accompany me to dinner."
For a moment, Elena was stunned into silence.
"Are you deaf or just plain stupid?" She asked.
"Ouch. And it's called being persistent," Damon said, totally unaffected.
"I'm not going out with you and there is nothing you can do to change my mind," she said, crossing her arms over her chest.
Damon stood up slowly, his eyes never leaving hers and against all her strength, her heart started beating a little faster. He walked close to her like a predator stalking its prey.
"I'm sure if I asked all the nice folks in this restaurant you'd change your mind," he threatened.
She narrowed her eyes, ready and willing to play with fire. She took a deliberate step forward and poked a finger to his chest.
"I'd like to see you try," she said quietly, "Oh, and if you didn't know, that was me calling your bluff."
They stood there, eyeing each other down, for a few moments before Damon took a step back, shrugged his shoulders and said, "Suit yourself."
Then he took a few steps away from her and turned to the main floor of the restaurant.
"Ladies and gentlemen, we have a special event for you tonight," Damon called out, effectively getting the attention of every living thing in the room. The walls started to feel like they were closing in and suddenly Elena was having a hard time breathing, but she was frozen, completely unable to do anything to stop him.
"She seems to be having a hard time agreeing to go out with me and I was thinking that maybe you fine folks would change her mind," Damon's voice continued to float in her ears.
"Ok I'll go out with you!" She called out to him when she finally snapped out of her trance.
"No, no, Elena. I want you to go because you want to," Damon said, an amused look on his face matching all the amused faces in the restaurant.
"I want to!" She said frantically, trying anything to shut him up.
"Want to what?" He asked, feigning innocence.
"I want to go out with you!" She hissed.
"Ok, ok, we'll go out," Damon said, putting up his hands in surrender. She narrowed her eyes at him.
"That was low," She snarled at him when he walked back over to her.
He ignored her comment and just smiled before asking, "What time do you get off?"
"Eight," she said in an annoyed voice.
"Ok, I'll see you then!" Damon said before he left the restaurant.
She was absolutely mortified the rest of the night. She received comments from all her co-workers and some of her customers. However, some of them gave her large tips because of her "ordeal".
Eight o'clock came sooner than she was ready for as she hung up her apron and took her stuff out of her locker in the back room.
Damon was waiting for her when she walked out of the front door of the restaurant. He looked amazing. He was wearing jeans, a dark blue button up shirt, and a black blazer. His eyes were shining brighter than she'd ever seen him, which could've been because of the genuine smile on his face.
To her dismay, she found herself smiling back at him.
"I'm underdressed," she said, angry at how disappointed she sounded.
"Actually, you're dressed perfect," he smirked at her before opening the door to a black Mercedes.
She slid across the cool leather of the seats and he dropped into the seat next to hers.
"You have your own driver?" She asked skeptically.
"You forget who I work for," he said with a smirk, but something about it didn't hit his eyes.
Twenty minutes later they pulled up to one of the nicest restaurants in New York City, she knew because she had applied there and was firmly rejected after her interview.
She looked out the window and saw the canopy covered entrance to the high class restaurant. There were people milling about in front of the doors and she wondered if that was a regular occurrence on Friday nights.
Damon opened the door and stepped out before reaching a hand in to help her out. She hesitantly took it and the minute she rose out of the car, all those people milling about pulled out their cameras and flashes started blinding her every way she looked. She heard Damon cursing softly and pulling her along into the restaurant. She kept her eyes on the ground while Damon battled through the walls of paparazzi before they found refuge in the restaurant.
"I am so sorry," Damon said once they were inside, "They are going to be taking pictures of us all night."
As if to prove his point, flashes started coming in through the windows. And then an idea dawned on her.
"I have an idea," she said as she grabbed his hand and dragged him through the restaurant.
"Where are we going?" He asked as she pulled him through a door clearly labeled "Employees Only".
"I had an interview here once and I remembered there is a back door right through here," she explained as they burst through another door and found themselves in an empty alley.
She ignored his questioning as she dragged him through the alley and expertly hailed a taxi before pushing him in and climbing in after him.
"Wow," was all he said after she rattled off an address to him and sat back in her seat.
She just smiled in return.
"Do you often find yourself outrunning the paps?" He asked.
"No," she laughed, "But I have had to outrun bad dates."
He found himself so comfortable in her presence. She was incredibly easy to talk to and he couldn't help but feel please that she was starting to relax around him.
He couldn't believe that the paparazzi knew he'd be at that restaurant tonight. He was livid, because he sure didn't tip them off. Elena surely wouldn't go out with him again when she saw herself listed as Damon Salvatore's New Woman in the papers tomorrow. So he decided he'd at least have fun with her tonight, in case she never wanted to see him again.
They pulled up to a small hole in the wall place and Elena dragged him inside to order their food. It took a total of about seven minutes for their order to be called before she was dragging him through a small door and into an elevator.
"You aren't taking me somewhere secluded and quiet so no one can hear me scream when you murder me, right?" He asked.
She stared at him for a solid minute before she cracked up laughing. She was so beautiful when she laughed like that. He mentally made a note to do that more often.
She finally calmed down as the elevator dinged at the top floor and she dragged him out and up two flights of stairs before bursting through one last door.
He found himself on the roof. There were lights strung about and a makeshift bed in a corner with pillows and blankets.
"What is this?" He asked in awe.
"I discovered this beauty when I first moved to the city and I wasn't used to the noise yet. I would come here to eat all the time and the owner overheard me complaining about not having a quiet place to study. He told me I could study up here and now it's my favorite place in New York," she explained as they sat on the bed to start into their food.
"So tell me about yourself," he asked. A flash of surprise touched her features before she contemplated her answer.
"I'm from a small town in Virginia, I moved here to go to NYU for pre-med. I graduate in May. And that's about it," she said simply, "What about you?"
"I was born and raised in the city. My father has raised me to take over the company. I went to school at Columbia and graduated with a degree in advertising," he said.
"How do you feel about the paparazzi always being around?" She asked quietly.
"I hate it," he said, "They are everywhere. I know I've made mistakes, but I should be allowed to make those mistakes without the nation knowing."
He had a hard time reading her reaction.
"I never thought about it like that," she admitted.
"Most people don't," he smiled, "But people can't get enough of this face."
He broke the heavy tension easily. That's what he was good at. He didn't do heavy and he wondered how he even ended up in a conversation like that with Elena. With most woman he'd stop it before it began, and he usually was around women who didn't care.
Something was different about this one. She was happy, she was beautiful, and she was quick. He knew she was someone he wanted to see again and that scared him. What if she didn't want to see him? What if he put himself out there and got shot down? He had spent years making sure he was never in this position. He went from one night stand to one night stand where no feelings were ever involved and now here he was on a first date with a girl he wanted to see again and again. He wasn't sure how he felt about that.
The taxi ride to Elena's apartment was enjoyable. She always had something to say, but yet she would listen to everything he said just as actively.
He was in over his head with this girl after only one date. He wasn't sure how he'd handle rejection from her.
They got out of the cab when it arrived at her apartment and he walked her to the door of her building.
"Thank you for coming tonight, I know I guilted you into it, but it was worth it," he said with a wink.
"I actually had a good time. Thank you, Damon," she said with a small smile. Then she turned to go inside.
"Wait," Damon called and she turned around, "When can I see you again?"
This was it. His hands were a little shaky and he took a deep breath to steady his nerves.
"You're the one who found me, I'm sure you can figure something out," she returned his wink before disappearing into her building.
He didn't realize he was smiling until his face started hurting.
Present Day
"Do you remember our first date?" Damon asked out of nowhere.
Elena smiled thinking of it as she fussed over her spaghetti sauce.
"When we got stalked by the paparazzi?" She laughed. His laughter joined hers.
She turned to face him as she refilled her wine glass.
"I swear I thought you'd never speak to me again after that," he admitted.
"You're face was priceless when they started taking pictures," she snorted.
Companionable silence fell over them as Elena finished up their meal. She knew the heavy conversation was coming, but she was enjoying their easy banter. It was incredible how easy it was for them to slip back into it as if the past five years had been a mere five minutes. How she wished that was the case.
He stood up to help her set the table and when his hand brushed against hers, she felt the once-familiar jolt of electricity. When their eyes locked, she knew without a doubt that he felt it too. He moved just a little too quickly after that and she was afraid that their fragile friendship they created would crumble at any second.
They sat and ate in silence for a few moments and she knew her free pass was up. She took a deep breath and steadied herself for the moment that she never thought she'd have.
"What happened to us?" She asked quietly. Damon stopped eating for a few moments before he answered.
"You left," he stated simply.
"And it's one of the worst mistakes I've made in my life," she said earnestly.
"Then why did you do it, Elena?" He asked.
"I was blackmailed," she responded.
Most of you guess that Elena was blackmailed, but no one has guess what she was blackmailed with... hmmm. Well, we'll find out next chapter before we start covering a LOT more of their backstory and then move onto covering MUCH more of their present day story.
Anyway, thanks for reading and thanks for being such wonderful readers! I'm excited to see what you guys think of this chapter!