I had intended for this to be two chapters, but after your wonderful comments on the last chapter, I decided I had to post the date this chapter. Which means its long. But it also has a lot of background information. What better way to fill in some back story than first date conversation?

The restaurant they go to in this update is one of my local favorites. And Damon ordered one of my favorite side dishes. ;)

Thanks so much for reading - I hope you enjoy this one too!

Disclaimer: I don't own Vampire Diaries.

"You're here again?" Damon asked as he walked into the kitchen the next morning wearing nothing but pajama pants, his hair sticking out in all directions.

"l live here," Stefan replied through a mouthful of waffle.

"No, you live in Charlottesville."

"Well, if that's the argument you want to make, you live in New York and yet, here you are."

"I do live in New York," Damon confirmed. "But it's a hell of a lot farther from here than your 45 minute trek." He poured himself a cup of coffee and located the creamer in the fridge. "And I'd be in New York right now if Giuseppe didn't have such a rip roaring sense of humor."

"There's some waffle batter left if you want one," Stefan replied, ignoring the comment about their father. Damon toasted Stefan with his coffee mug in response. Stefan took another bite of waffle, watching as Damon made a production of stirring cream and sugar into his mug. "Rumor has it you walked Elena Gilbert home from The Grill last night." Damon looked at him over his coffee mug.

"I forgot nothing is a secret around here," he said before taking a dreg from his mug.

"There are plenty of secrets in this town," Stefan said. "They just don't get broadcast in broad daylight."

"Technically, it was dark," Damon pointed out.

"You know what I mean." Damon moved to return the creamer to the fridge and took out several pieces of fruit while he had the door open.

"I wasn't going to let a girl – especially an attractive girl like Elena – walk home alone. Mystic Falls is the perfect setting for a horror movie. It's the kind of place where nothing bad ever happens which means it's one rapist away from being featured on the next episode of Unsolved Mysteries. I saw Elena to her door safely. The end."

"Is it?" Stefan asked. He knew his brother well.

"Well, I am taking her to dinner tonight," Damon said, taking another swig of his coffee. "So there's that."

"Damon," Stefan warned.

"What, is that awkward for you?" Damon replied, feigning interest. "I believe the two of you dated. I'm sure it must sting just a little bit to see her hitting it off with your older, better looking brother."

"Elena is a good person," Stefan replied, once again letting one of Damon's comments go. "She doesn't deserve to be led on."

"And does darling Rebekah know how you're rushing to Elena's defense?"

"Rebekah knows Elena and I are friends. Rebekah and Elena are friends. And Rebekah – who just left a few minutes ago – agrees with me on this. Don't screw with Elena."

"I'm just taking her to dinner," Damon said. "Everyone has to eat sometime."

"Don't lead her on," Stefan warned. "She deserves more."

"More than your screwed up big brother?" Damon challenged, getting the jest of where Stefan was going with his comments.

"Your reputation precedes you, Damon. You did it to yourself."

"Yeah, well, I'm out of here as soon as Chester reads the will. Then you and your bombshell British girlfriend can officially sign your names on the deed of this house and live happily ever after with no inconveniences from me. Although, I will be talking my car back to New York. I'd rather not leave it here. You understand."

"What makes you so sure Dad didn't leave you the house?" Stefan asked. Damon snorted.

"Who else would it go to? You were his favorite, the good son. I was the Salvatore screw up. Dad's last laugh is making me executor so I have to be there to oversee his legacy being handed over to you." Stefan sighed.

"He loved you, Damon. You just chose to believe what you wanted." It was the same sentence he'd been saying often since Damon arrived in Mystic Falls a full day after their father took his last breath.

"And you choose to believe that," Damon countered, using the same response he'd used several times already. He swigged from his coffee again.

"You blame me for Mom dying," Stefan said. It was a comment that had been brewing just under the surface for a long time. "But it wasn't my fault." That was enough for Damon. He had avoided this conversation for 26 years. He wasn't going to have it now.

"You know, I think I'll go out for breakfast," he said, leaving the fruit and waffle batter on the counter along with his nearly empty coffee mug. He turned and started to walk away.

"And don't think I don't see the resemblance between Elena and Katherine," Stefan continued. He knew he was hitting low, acting childish, even, but he wanted to get a rise out of his brother, provoke some kind of emotion besides the apathy he'd been wearing since arriving in Mystic Falls. "The dark hair, dark eyes. They're even the same build. It's eerie, how much they look alike." Damon looked over his shoulder at his younger brother.

"Looks like I have a type," he said evenly. "And little brother? Malice doesn't suit you."

With that, Damon headed upstairs, turned on his shower and stripped off his pajama bottoms. Stepping under the hot spray, he let his thoughts drift.

He hadn't missed the fact that Elena looked remarkably like his exe. As Stefan had so boldly pointed out, they had the same dark hair and eyes, were built similar, petite yet strong. He'd be lying if he said Elena's uncanny resemblance to Katherine hadn't been what first caught his attention. But unlike Katherine, Elena exuded warmth. Her smile, so kind and welcoming in itself, reached her eyes and her laugh was light and earnest. Katherine had been cold and calculating with a sinister smile, her laugh usually forced or at the very least, at someone else's expense.

Katherine certainly couldn't debate literature with him. She preferred to discuss her latest expensive purchase, her next modeling gig. Not that she wasn't intelligent. She was a gifted manipulator, talented at spinning any situation to leave her name free and clear. That was part of what made them such a power couple, her seductive, him ruthless at the negotiating table. They got what they wanted. Until she didn't want it anymore.

Damon shook his head under the shower spray. He couldn't, wouldn't, think about Katherine. Or his brother. Or their dead parents. He was going to get dressed, find some breakfast, avoid his brother and promptly at seven o'clock, he was going to take Elena Gilbert on a date. He'd figure out the rest later.

"Are you sure this looks okay?" Elena asked, studying herself in the full length mirror. "He didn't say where we were going, just to 'wear something pretty.'"

"You look hot," Caroline confirmed.

"I'm not sure hot is a good thing," Elena said, scrutinizing her appearance.

"That's the right dress," Bonnie said from her spot on the bed. "Damon will be eating out of the palm of your hand." Elena made a face.

"I'm not sure that's what I want. He doesn't need incentivizing."

"Have you seen Damon Salvatore?" Caroline asked. She rummaged through the selection of jewelry laying on Elena's bed. "You do, in fact, want that."

"Caroline," Elena chided. "Tyler. Remember him?" Caroline just shrugged.

"I don't know," Bonnie said, picking up a bangle from the pile of jewelry and surveying it. "I have a good feeling about this." Both Caroline and Elena turned to look at her. "Not this one. It's too – plain. Wear the gold pave bracelet." She noticed then that her friends were looking at her. "What?"

"Is this another one of your hunches?" Caroline asked. Bonnie was infamous for her spurts of intuition, gut feelings about people and situations that tended to turn out exactly as she thought they would. It was scary, how accurate her hunches tended to be.

"I just think it's a good thing, Elena going out with Damon," Bonnie said with a shrug. "He's got a bad boy streak and Elena, I love you, but you could use a little danger in your life. You play it too safe."

"Again, you sound more like Caroline than Bonnie right now," Elena said. "I fully expected you to be the rational one and tell me how bad of an idea this is. And yet, you're encouraging me."

"I just want you to have some fun," Bonnie said. "Even if it's with Damon Salvatore."

"What does Stefan think of you going out with his brother?" Caroline asked. "Or does he know?" Elena sat down at her vanity and started to touch up her makeup.

"He knows," Elena confirmed. "Damon told him this morning. He called me this afternoon to ask if I knew what I was getting myself into."

"And do you?" Bonnie asked.

"Nope," Elena admitted. "But like I told Stefan, it's just dinner. And Damon doesn't even live here. He'll be gone back to New York, back to his life as big city sports agent, as soon as he can be. It can't hurt to have dinner with him while he's here."

"Free dinner," Caroline said with an appreciative nod. "I like your style, Elena Gilbert. No expectations." Bonnie didn't say anything. She picked up a pair of earrings and wordlessly passed them to Elena. Her gut told her, loud and clear, that this was going to be anything but just dinner.

Promptly at seven o'clock, Elena stepped out onto the porch with the intentions of waiting on the swing for Damon, only to find him already parked on the street, leaning against the same blue Camaro she vaguely remembered from her childhood. Instead of puffing on a cigarette like he did in her memories of him, he was merely watching her, his arms crossed over his chest.

Elena paused on the top step, just to take him in. He was wearing black jeans and a midnight blue dress shirt, a casual black sports jacket over it, and black Italian dress shoes. The color of his shirt made his vivid blue eyes stand out even more. She couldn't help but smile at her good fortune. She had no intentions – nor hopes – of anything long term with Damon, but she was certainly going to enjoy looking at him throughout dinner.

Damon felt his heart quicken when Elena stepped out onto her front porch. He'd arrived a few minutes early, mostly because he was bored at home, but also because he was admittedly looking forward to seeing Elena again. He'd intended to wait until seven o'clock, walk to Elena's door, and pick her up like a gentleman, but she had beat him to it. She was appraising him from her spot on the porch, but he didn't care. He was doing the same thing to her. She wore a simple blue sleeveless dress that fit her in all the right places and hit her at a length that showcased her toned legs. Her hair hung in loose waves, a departure from her usual straight locks, and flowed behind her as she descended the stairs and approached him. He pushed himself off his car to greet her, counting his lucky stars that he was the one she was going out with tonight.

"Hey," he said.

"Hi," she replied with a timid smile. "You got here early."

"I wanted to make a good impression," he replied smoothly. "You look beautiful, Elena." He felt a sense of accomplishment at the faint blush that crept into her cheeks.

"You cleaned up pretty well yourself," she told him. She looked past him towards his car. "I can't believe you still have that thing. I remember you driving it when I was in middle school." Damon glanced over his shoulder at his car, one of the few material possessions he owned that also contained sentimental value, and shrugged.

"It was my mom's," he explained. "I like to think of her as the coolest chick in town way back when, driving around in this thing." He'd never actually been given the car, but the day he'd turned 16 and got his license, he'd taken the keys from their place on the kitchen key rack and no one, not even his father, had questioned him. He had never quite understood why Giuseppe hadn't intervened. A 16 year old kid didn't have any business driving around in a muscle car. At 32, he still didn't have much business behind the wheel of it.

"She at least had their attention," Elena agreed with another glance at the car.

"You ready to go?" Damon asked.

"I am," Elena confirmed. Damon reached behind him and opened the passenger side door.

"Then your chariot awaits." Elena smiled at him before sliding into the car. It was spotless, the leather seats original, but still like new. It smelled like saddle soap, aftershave and something that was strictly vintage. The scent calmed her as Damon slipped in behind the wheel and cranked up the car. She could feel its power, just from the idling of the engine. It both scared her and thrilled her as she took in how comfortable Damon was behind the wheel.

"Where are we going?" she asked as he pulled away from the curb.

"Charlottesville," he said. "I figured our options were limited in Mystic Falls. I made reservations at a place called Maya. The offensive coordinator for UVA's football team recommended it."

"Offensive coordinator?"

"I'm after one of their seniors. Kid's going to be first round draft pick for sure."

"After him? As in to be his agent?"

"Yep," Damon confirmed. "He's not only a phenomenal athlete, he's also got this good guy thing going on – volunteers at the children's hospital, has a 4.0 in something besides art. He's an agent's dream – a big contract to play pro, endorsement deals, good PR. But that's enough about work. What'd you do today?"

Elena launched into a recap of her day and asked Damon about his as the car rumbled down Highway 29. The 45 minute drive went by in a flash and soon, they were being seated at their table. The restaurant was upscale but not stuffy, the lights dim, but the atmosphere warm. Damon pulled her chair out before seating himself and their waitress appeared almost immediately to fill water goblets and take drink orders. Damon looked at Elena and took a deep breath. There was something he needed to get off his chest before the night went any further.

"Elena, I want to apologize again for last night. About your parents. I didn't know they'd passed. I hope I didn't upset you." Elena gave him a soft smile. He was being genuine, looked anxious now that he had issued his apology.

"It's okay," She assured him, reaching out to touch his hand. The contact was brief, but it was enough to send a surge of electricity through both of them. "It's been a long time, Damon. I miss them every day, but I'm okay." Damon felt a surge of something – admiration, perhaps – at how strong she seemed to be. His own mother had died twenty-six years ago, but her death still caused him a tremendous amount of pain if he let himself think of her more than a brief moment once in a while.

"If you don't mind my asking, how long ago was the accident?"

"Ten years this past May," Elena answered. "Sometimes it feels like yesterday, other times it seems like it was a century ago."

"I know what you mean," Damon said more to himself than to Elena. The waitress reappeared with their drinks and they placed their orders after taking a few moments to browse the menu. "So Alaric is married to your Aunt Jenna?" he asked when the waitress left their table.

"He is," Elena confirmed. She remembered something about Damon then. "You and Ric were best friends, weren't you?" Damon shrugged.

"We were the best friends we knew how to be," he said. "Neither one of us were much on personal relationships, but we both liked fast cars, cigarettes and booze so we bonded." He purposefully left out that they had shared an affinity for loose women as well.

"His high school stories make me laugh," Elena said. "He's such a responsible adult now, teaching history, being a husband and a dad. It's hard to believe him when he talks about drag racing over by Oak Ridge or boxing in the gas station parking lot."

"What'd he tell you about the drag racing?" Damon asked curiously.

"That he won." Damon scoffed.

"Liar," he exclaimed. "I kicked his ass every single time he put his Mustang up against my Camaro."

"I'm going to tell him you said that." Elena's eyes sparkled with amusement.

"Please do," Damon told her. "I have a reputation to uphold." Elena rolled her eyes playfully. "He and Jenna have a daughter, right? He was telling me about her at Mystic Grill last night.'

"Ella," Elena confirmed. "She's two and my favorite person in the entire world."

"Beside me," Damon corrected with a grin.

"You're going to have to grow pig tails and wear monogrammed smock dresses before you take that position," she told him seriously.

"I'll see what I can do," Damon replied, making Elena laugh lightly. He decided right then and there that her laughter was the best thing he'd ever heard and made it his goal to hear it as much as possible. "You mentioned at the coffee shop the other day that you'd been to New York. When were you there?" Elena raised an eyebrow slightly, impressed that Damon seemed to remember every detail of their few conversations.

"I actually lived there," she told him. She watched as his eyebrows raised in surprise.

"Really?" She nodded her confirmation.

"I went to Columbia for undergrad, then I stayed for a while, working and writing. I've been back in Mystic Falls for about a year."

"You were in New York for the better part of the last decade?" he asked. "You should have looked me up. Granted, it took me until about three years ago to actually commit to one city, but I've been calling New York my home base for a while."

"Stefan told me I should call you a couple of times," Elena told him. "I think he even gave me your number once. I just never got around to it."

"Shame," Damon said with a shake of his head. "We could have done this a whole lot sooner." Elena smiled at him and decided it was her turn to ask the questions.

"How'd you get to be a sports agent?" she asked. Damon took a long swig of his drink, deciding to give her the brief, more PG version of how he'd ended up falling into a career he loved, despite a proper college education to prepare for it.

"Long story short, I was in the wrong place at the right time. A game of pool took a turn, I did some fast talking to get me and a buddy out of a tight spot. A guy that was an executive at a smaller firm overhead and persuaded me to come work for him. I took to it like fish to a water and here I am."

"Do you still work for him?" Damon shook his head.

"We parted ways about six months after I started working for him. Mutually. He was a good guy, just couldn't afford to keep me on. I went to work for one of the top firms in the industry, stayed with them a few years. I left last year to strike out on my own, took most of my clients with me. It keeps me busy, but it's nice, not having to give up part of my earnings to the firm or find someone to sign off on my decisions." Elena saw the passion in his eyes as he talked about his career. She found him all that more attractive.

"You love it," she stated.

"I do," he confirmed, leaning in. "And you, Elena, lied to me." Elena frowned.

"About what?" she asked.

"I asked if you'd written anything I might have read. You said no. But it turns out, I read this great book, Turning Home, while on a flight to London for an NFL international game between the Steelers and Vikings." Just as he'd suspected she would, Elena blushed and busied herself with the bread basket that had arrived sometime during their conversation.

"You read that?" she asked timidly.

"Given the 'New York Times bestseller' stamp on the cover, I'd say a lot more people than just me read it."

"It's not that great," Elena said with a shake of her head. Damon reached across the table and mimicked her move from earlier, lightly putting his hand on top of hers.

"Elena, it was fantastic," he said truthfully. "I really enjoyed it. So much so that I borrowed Stefan's copy to read again."

"Thank you," Elena said softly. He had removed his hand, but hers was still on fire from his touch. "Despite my whole 'it's not that great' thing, I really am proud of it. But how did you figure out I'd written a book?"

"Stefan," Damon answered. He looked slightly guilty. "I wanted to read some of those articles you mentioned before tonight and so I asked him if he had any laying around. He turned up a little while later with a couple of magazines and a book with your name on the spine. Although I couldn't help but notice he has a signed copy which means I will be purchasing a copy of my own to have you autograph. Can't let little brother one up me in the literature department." Elena shook her head, but was grinning.

"How'd you end up back in Mystic Falls?" Damon asked. "Not exactly the same vibe as New York."

"It might sound crazy to you, but I missed this place," Elena said. "Its home, you know? I loved New York. It was big, and loud and creative and inspired me. But what family I have is here. My parents are buried here. After a while, New York went from being one big adventure, to one big hassle. After my book did so well, I decided it was time to move back here, reconnect with my old life. We all kept in touch – my family, my friends – but we went our separate ways after high school. Funny, really, how we all ended up back here."

Damon looked at Elena contemplatively. Just as she had called him out on how much he loved his career, he could tell she loved Mystic Falls. It was her home. It triggered something down deep inside him. He wasn't quite sure what it was, but it was a foreign emotion he added to his shelf of feelings to deal with later.

"Have you ever eaten at that tiny sushi place between Houston and Bleecker in Greenwich Village?" Elena asked.

From there, the conversation flowed, Elena telling Damon about all of her favorite New York haunts, many of which he frequented himself, Damon telling her stories from his travels to various pro sporting events across the country and in a few instances, the world. They talked and ate, Elena teasing Damon for ordering an extra side of the white cheddar grits which he defended by saying he only got proper grits while in the South. Too soon, Damon was paying their bill and they were back in his car heading home. Somewhere along the way, Damon had found her hand in his, their interlocked hands resting on the console between them.

"Stefan must really be glad to have you home," Elena commented.

"More like eager to see me on a plane bound for La Guardia," Damon replied. There was something in his voice that Elena couldn't place, a mixture of tension and disappointment.

"I'm sure that's not the case," Elena said, even though she knew Stefan and Damon didn't have the best relationship. Stefan didn't talk about his brother much, didn't indulge in sharing why their relationship was so strained, but Elena couldn't accept that they didn't care for one another at all. They were family, after all. Brothers.

"Stefan and I lead very different lives," Damon explained. "He's straight laced, always has been. I got in my fair share of trouble growing up – and if I'm being honest, I kept it up once I left here. He and I will never see eye to eye on pretty much anything." Elena nodded and let the topic drop.

"So how long are you planning on being in town?"

She hadn't actually meant to ask the question. She'd gone into the date knowing Damon was essentially just passing through. But it had been a really long time since she'd been as drawn to a member of the opposite sex as she was to Damon. Even as she told herself getting too close was a bad idea, it was like something inside of her – and out of her control – was pushing her towards Damon.

"I don't know, another couple weeks or so," Damon said, his eyes on the road. He couldn't believe the words coming out of his mouth. It was Wednesday. The reading of the will was set for a week from now and he'd been planning to hop on a plane northbound as soon as it was over. But now, he felt less in a hurry, less compelled to get back to the city. He wasn't sure he liked it, the seemingly waning pull of the city, but the idea of staying in Mystic Falls even a few minutes past his initial departure plan didn't seem like the worst thing in the world at the moment.

The Gilbert house appeared in front of them as they turned a corner. It was dark, but the porch light burned bright. He pulled to a stop in front of her house and cut the engine. He absentmindedly grazed the back of her hand with his thumb.

"Here we are," he said. Elena smiled at him.

"Thank you," she said. "For tonight. I had fun." Damon lifted her hand and pressed his lips to the back of it.

"Of course," he said. He took just a brief moment to take her in once more before he relinquished himself to the fact that it was time to part ways. "Let me walk you to your door."

"You don't have…"

"Elena," Damon cut her off. "I'm walking you to your door." With that, he was out of the car and pulling open the passenger door for her. He offered his hand and felt both the increasingly familiar electricity shoot through him and a sense of relief that her hand was back in his. He placed her hand at his elbow and walked her down the sidewalk as chivalrously as he knew how to do. At the top of her porch stairs, they turned to one another.

"Thank you again," she said. Damon gave her a soft smile and shook his head slightly.

"Anytime," he told her. He reached out and brushed a lock of hair away from her face. If she was any other woman, he'd already have her pressed up against her front door, aiming to be invited inside. But Elena commanded his respect, even though he knew she was completely unaware of it.

Elena looked up at him, trying in vain to decipher what he was thinking. She could tell there was more to his story just below the surface and she found herself wanting to know it. She also desperately wanted him to kiss her as her dark eyes landed on his.

"I should be thanking you," he said. "It's been a while since I had the pleasure of spending time with someone not only beautiful, but intelligent and kind as well." He could hardly believe the words that had just came out of his mouth. They were true, but he wasn't one to say things like that, particularly when he planned on sleeping alone in his own bed that night.

"Now who's the liar?" she asked him with a coy smile. He chuckled lightly.

"It's true," he told her. Her hand still in his, he gently pulled her closer and slipped his free arm around her waist. Both of their bodies hummed at their proximity. Before he could stop himself, he leaned down and touched his lips cautiously to hers.

Without warning, fire erupted somewhere deep inside him. He kept himself in check, even as he deepened the kiss and pulled Elena closer, but he knew this kiss was different. Different how, he wasn't sure, but instinct told him Elena Gilbert possessed the power to bring him to his knees. He made himself pull away after a few long moments, determined not to take it as far as he wanted to.

"Goodnight, Elena," he whispered huskily, his forehead resting against hers.

"Goodnight, Damon," she replied, a slight shake in her voice as she tried to catch her breath. Damon placed one last gentle kiss on her forehead before letting her go.

"I'll see you soon," he told her as he stepped way.

"See you soon," Elena echoed. She turned away then, fumbling with her keys as Damon's footsteps descended her porch stairs. She had managed to unlock the door and was just about to let herself in when she heard Damon's voice again.

"Gone With The Wind."

Elena turned to see Damon standing halfway down her sidewalk, his hands in the pocket of his sports jacket, the scene reminiscent of the night before when he'd asked her out. "What?"

"Gone With The Wind," he repeated. "You asked me last night what my favorite book was. It's Gone With The Wind." Elena smiled.

"Really?" she asked. "Why?" Damon shook his head with his infamous smirk in place.

"I'm going to need a second date before I tell you that." Elena's laugh accompanied him as he made his way to his car. Once he was sure she was safely inside – which wasn't until an upstairs light came on – he pulled away from the curve, a wide smile on his face.

As much as I'm loving writing Damon and Elena's story, I'm also loving writing out Damon and Stefan's. Those two have a lot of issues to work through.

I'd love to know what you thought of their first date! Look for the next update - one of my favorite chapters so far - sometime over the weekend!