A/N: I've had the last two weeks from hell. First my cat that I've had for almost six years died. Then, I finished this chapter and then my computer crashed, and it deleted it, so I had to re-write it. And then, my computer shut down when I forgot to save, so I lost it AGAIN. With my other cat, who've I'd only had for about a week, dying, I just had to take a small break, but I'm back now, and, hopefully, better than ever. There is some serious stuff down at the bottom of the chapter, talking about both Damon's past and Caroline's. Please be good – read & review!

"I could not wait to get away from that God awful party," Damon said, opening the front door of the Grill and waiting for Caroline to go through it. "Seriously, it gets worse every time."

Caroline took a seat across from Damon in a booth while he signaled Matt over. He ordered some French fries and a beer, then, looking at Caroline as she said, "I don't know, Damon, it wasn't that bad."

"Speaking of," he started, looking into her eyes, "When you were talking to Stefan, how did you learn to talk business like that? It was fucking brilliant."

Caroline smiled, "I own my own business, Damon. I may just be a dressmaker, but I've had to do my share of PR. You should learn how, it'd make you a better businessman." Caroline saw Damon's face fall, so she added, "Not that you're a bad one. It's just that…since you and your brother own that foundation, you should know how to talk to people."

"That foundation was my dad's. I had no interest in it at all. If that clause wasn't in his will, I wouldn't be doing this at all." Damon paused to take a drink of his beer, "I could sell my shares, but it's got to be approved by Stefan, which, it's not."

"I'm sure that you could get around that if you really wanted to."

Damon shrugged, "I'm going to be completely honest with you, Caroline. Stefan and I, our relationship has been kind of strained over the last few years, and we're finally on good terms. I love my brother, I really do, and with us owning this foundation and running it together, I don't want to screw up what progress we've made. I want to be friends with my brother again."

"So what happened?" Caroline asked, taking a few French fries off Damon's plate. She noticed Damon's quizzical look, so she continued, "Something had to have happened between the two of you to fuck up your relationship in the first place. What was it?"

Damon made a face and watched Caroline very carefully, "That's a long discussion for a different time."

Caroline nodded and said, "You should be happy. You're part of some kind of family heritage. I have nothing. I'm not a part of anything."

"Look at me, Caroline," Damon ordered softly and her eyes met his. "You're part of the Mikaelsons. They love you very much."

"It's not the same. My real family, my blood family, they're all dead."

Damon pushed away the urge to cup her face, "Caroline, blood doesn't always equal family. I bet if you asked Elena, she'd tell you the same thing."

"Why bring Elena into this?"

"Because she was adopted. She's not blood related to her parents, to Jenna, to Jeremy. That doesn't change the way that Jenna and Jeremy feel about her, does it?"

"No, but Miranda and Grayson Gilbert were actually allowed to adopt her."

Damon noticed that Caroline's gaze was fixed on the table in front of her, so he said, "Caroline, look at me." Her eyes raised and once again she was looking into his eyes, "Esther Mikaelson is your mother. Klaus, Kol, Finn and Elijah are your brothers. They don't need a piece of paper to know that you belong with them – it's fate. Esther was told she couldn't adopt you, but she's kept you around, she chose you. And the way that Klaus defends and protects you? I doubt he'd do that to just anybody off the street. You're special, Caroline, and they all know it."

"You think I'm special?"

Damon nodded, "Yes, I absolutely do."

Caroline blushed, "Damon, just because you compliment me and flatter me doesn't mean I'll fall into bed with you."

Damon nodded, "I wouldn't have it any other way."

-x-

Sitting in the coffee shop across the street from Caroline's shop, Damon just watched out the window. It had been a couple of weeks since their "date" at the Salvatore foundation party, and she was in his thoughts – all the time. It wasn't just a once in a while thing, either. She practically lived up there. He couldn't get rid of her. He wanted to ask her out, and had come all this way to Richmond for that very purpose. But when Damon tried to go into that damn shop to ask her out, he lost his nerve and wandered over to the coffee shop. Now he was sitting across the street, drinking some crap cappuccino and watching her shop like some stalker.

Damon was so enthralled with what he was doing that he didn't hear Esther come up and take the chair beside him until she spoke, "Lost your nerve, huh?"

Damon jumped a little, but then looked at her quizzically.

"I raised four boys, Damon. You like Caroline. I can tell; hell, it's written all over your face. So, when are you going to go over there and ask her out?"

Damon just shrugged.

"I'm going to help you out a little," Esther said, taking a slip of paper out of her purse and wrote something down on it. She handed it to Damon, "This is Caroline's number. You should give her a call."

Esther got up to leave, but Damon looked at her, "Do you think she'd ever go out with me? Like, a real date?"

Esther sat back down, sat her coffee cup on the table, and looked at Damon, "I'm going to give you some advice. When we first got Caroline, she was a mess. She was fifteen, and she hadn't really been accepted anywhere. She wouldn't look you in the eye, and she would definitely not spend any time alone with my sons. She was scared of them. She was afraid to take a chance – any kind of a chance. We were persistent, though, and eventually, she came around."

"What made her like that in the first place?"

"Damon, every family that Caroline had ever been with, they mistreated her. They were only nice to her when they wanted something, and after they got it, her name was lower than mud. She's been abused and hurt. But it isn't my place to tell you all about it. That's Caroline's."

"If Caroline went through all that," Damon said, thinking out loud, "Then there's no way in hell she's going to give me the time of day."

"I love Caroline like she's my own daughter. I cannot imagine my life without her in it. My advice to you is to be persistent. Ask her out. And even if she says no, keep trying. Show her how you feel."

-x-

"You don't understand what I'm saying, Nik," Caroline said into the phone. "I can't ask Damon Salvatore out on a date."

"Why not?"

"Because."

Klaus laughed, "Caroline, you know that's not a real reason."

Caroline rubbed a hand over her face, "What does it matter to you, anyway? You hate Damon."

"I don't hate him," Klaus defended, but Caroline cleared her throat and he laughed, "Okay, so I dislike him very much. But you know what? It's just a date. You don't even have to start a relationship with him, just ask him to dinner or something. Caroline, it's been almost four years since you broke up with Tyler and I think you need to get back out there and see what the world has to offer you."

Caroline sighed, "I like him, Nik. I mean really really like him, and I can't do that."

"You're afraid of falling in love again, Caroline. I get it, I really do. But you can't go through your life afraid."

"Look at everything I've been through, Nik. I have every right in the entire freaking world to be afraid. There are people out there who just…" her voice trailed off and she shuddered. "They use you up and spit you out and don't give a damn about what you want, or what you need, or even who you are. Remember the son of my first foster parents?" Caroline heard Klaus groan, so she knew that he was well aware of what she was talking about. "He used me up and spit me out, and then made it out to be my fault. He manipulated me like no one ever has before or since." She sighed deeply, "He proved to me that there is no such thing as a good guy."

"Well, that hurts my feelings."

"Nik, I love you and your family. You guys accepted me when nobody else did. You guys are the one good thing to come out of the system for me, and I love you all like you were my real family. But, with everything I've ever been through, I've gotta be getting punished for something."

"There is no one in the entire world, not even the biggest rapist or murderer, that should be punished as much as you have. Now, go to Damon and ask him out. A date wouldn't kill you."

Caroline rolled her eyes, "Be careful, Nik. You're starting to sound like Elena."

"I knew I liked that girl," Klaus laughed. "Go, Caroline. It'll be good for you."

"Now you really sound like Elena."

-x-

"You sure he's not here?" Caroline asked Matt for what seemed like the hundredth time. She had driven to Mystic Falls as fast as she could, and it was all because of Klaus and Elena. Caroline thought she was going crazy; why the hell would she drive almost two hours away to ask out some guy? It didn't make sense; Caroline would've never done that before, not ever.

Matt laughed, "No, Caroline, he's not here. Just because I work for Damon doesn't mean I know where he is every second of the day."

Caroline rolled her eyes, "Look, Matt, I don't even have his phone number and –" it was at that second that her phone started to ring. She gave Matt a dirty look for laughing and put it up to her ear, "Hello?"

"Hey, Caroline, it's Damon."

"Damon, where are you right now?"

"In Richmond."

Caroline rolled her eyes, "And I'm here, at the Grill, looking for you. What are you doing there?"

"I was going to go and see you, but I kind of got sidetracked."

"I want to talk to you in person, Damon. How long would it take for you to get here?"

"I'll be there as soon as I can."

"I assume you'll be waiting for him here, then?" Matt asked Caroline when she hung up. She looked at him, "You know, eavesdropping is not very nice."

"You have a very expressive face, Caroline. It's easy to read what's going on with you."

Caroline stuck her tongue out at him. He laughed and said, "Since you're waiting, do you want me to get you something to eat?"

"Yeah, sure. I'll take a cheeseburger, please."

While she sat there and waited, Caroline's mind thought back to her past. Her past relationships had just been sad. She had a pretty pathetic dating history, so why would Damon even want to go on a date with her? The way she was treated in the foster home before Esther took her in, they really did a number on her and made her feel hideous. Nothing she did was ever right, and apparently she was not dating material, either.

Matt brought out her burger and said, "Do you want some company?"

Caroline shrugged, "Sure, I guess."

"So when are you and Damon going to stop dancing around the facts and just go out already?" Matt asked as he slipped into the seat across from her.

Caroline watched him carefully, "Excuse me?"

Matt shrugged, "It's none of my business, Care, but there's obviously a spark between you and Damon, and if you haven't noticed it, then you're more oblivious than I thought. He likes you, Caroline. Damon hasn't acted this way around a girl in years."

"Yeah, right," Caroline said, taking a bite of her burger. When she swallowed, she finished, "He probably just wants to get me into bed."

"Caroline, if all Damon wanted to do was get you into bed, he would've done it already," Matt said. He watched her carefully before adding, "I'm not saying anything bad about your character, it's just…Damon has had a fling with almost every girl in town. Everybody except for Bonnie and Elena."

"Even Jenna?" Caroline asked, mentioning Elena's aunt who had practically raised Elena and Jeremy since they were teenagers. Matt nodded.

"For a long time, Damon wasn't looking for a serious relationship. He just wanted flings, and every girl in town wanted him. For Damon, it was a win/win situation."

"Are you telling me not to ask him out?"

"No, it's not what I'm telling you. Caroline, I understand you've been hurt in the past, but Damon's not going to hurt you. He knows what the word 'no' means and he respects that. He's a good guy."

Caroline shook her head, "No, there's no such thing as a good guy."

"What about your brothers?"

"Do you know Nik?" Caroline asked him, but then realized, "Oh yeah, you were at the founder's party fiasco. Well, Nik is a good guy. So are his brothers, Matt, but they are the exception."

"Caroline, give him a chance," Matt said, watching the front door. He noticed that Damon had just walked in so he said, "Good luck," and he went back to the bar.

"I didn't expect to see you here for another hour or so," Caroline said to Damon, looking at her watch. Damon nodded and took a seat across from her.

"I made good time."

Caroline gave him a knowing look, "You drove like hell to get here, didn't you?"

Damon grinned, "A little."

Caroline avoided Damon's gaze and said, "Listen, Damon, I'm not good at this because I've never actually been on one, but would you go on a date with me?"

"Caroline, I would love to go on a date with you. But tell me, you've never been on a date?"

Caroline shook her head, "No."

Damon's eyes got wide. "Never? As in never ever?"

"Look," Caroline said, looking at him, "I don't want you to feel sorry for me. I just…well, I was with Tyler, but he never took me anywhere he didn't have to, and before him, my dating life was pretty much nonexistent."

"You never went anywhere alone with Tyler? Not even to the movies, or a museum, a picnic in the park?" Caroline was shaking her head, so Damon said, "What about dinner? No? Not even once?"

Caroline shook her head, "No, Damon, I didn't. Look, Tyler was a no-account douchebag, okay? He kept me around for one thing and, at the time, I thought I deserved it. I thought I deserved someone like him."

"Nobody deserves some asshole who doesn't even take them on one goddamn date," Damon half muttered, but Caroline frowned.

"Look," Damon said, tilting Caroline's chin so she would look him in the eyes, "That wasn't toward you. You've must've been through some heavy shit to honestly believe you deserved that. Nobody deserves that."

"Look, Damon," Caroline said, pushing his hand away from her face, "Let's not go into the whole Caroline's only been with douchebags discussion. I've got Elena and Nik for that. They're telling me that I need to move on from the past. I agree with them, but my dating history is just…pathetic."

Damon made a mental note just then to make sure that this was the best fucking date of Caroline's life.

"How about I come pick you up tomorrow night? What do you say to about six? Can you get your work done by then?"

"Yeah, I can," Caroline said, smiling. "That sounds good."

-x-

It was around twelve-thirty when Elena answered her phone the next day, "What's up, Caroline?"

"Look, Elena, my date with Damon is in four and a half hours, and I need you to come over and help me get ready. This is my first actual date, so I don't know what to do, or what to wear, how to do my makeup –"

"Caroline, breathe," Elena said. "Everything is going to be okay. I'll be there in a couple of hours. It'll be okay."

Elena pushed end on her cell and looked at Stefan, "I've got to go to Richmond. Caroline needs me."

"What's so important?"

"She's going on a date tonight. With Damon," she added.

"Yeah, so?"

"This is what we wanted, Stefan. We wanted to get Damon out of the funk that he was in – and it worked. Caroline's crazy about him."

"How do you know that?"

"Because, Stefan, she's really nervous about going out tonight. She needs me over there. I need to be there for her. This is her first date."

"First date…as in very first?"

Elena nodded, "Yes. She's got a bad history and no guy has ever wanted to take her out before. That's why she needs me." She grabbed her car keys and her purse, giving Stefan a peck on the lips, "I'll be home later."

Elena got to Caroline's house in an hour and a half. She let herself inside, petted Caroline's dog, Lizzy, and started up the stairs. She went into Caroline's bedroom, where she was inside her closet, looking for a dress to wear.

"I'm here," Elena announced. Caroline turned around.

"I'm glad. Now you can help me figure out what the hell to wear."

"Move," Elena commanded, and Caroline got out of the way. She held up two dresses; one was deep purple and had flowers on it, and the other was light green and satin. "What do you think?"

"I'd rather wear the green one."

"Why?"

"Because it's never been worn before. I only made it about two months ago."

"Put it on," Elena said, tossing Caroline the dress. Caroline started to take her jeans off when Elena said, "So, you nervous about tonight?"

"I am. I mean, I really really really am. I don't think I've ever been this nervous about anything before in my life."

"Did you call Esther?"

Caroline pulled the dress over her head, "Huh?"

"Well, whenever a girl usually goes on a first date, they call their mother and let her know that they are going, to get advice or whatever. That's what I did."

"You were also fifteen years old, Elena."

"That doesn't matter." She looked at Caroline, "That color really suits you. Let's look through your shoes to see what you've got." Elena squatted down in Caroline's closet to look at her shoes and laughed, "You keep your shoes in a box?"

Caroline shrugged, "Well, I don't have a whole lot of a selection to get some fancy rack or anything. I've got a pair of black heels – black goes with everything."

Elena's eyes widened, "It so does not."

Elena picked up a pair of white strappy stilettos, "You wear these?"

Caroline shrugged, "Once or twice."

"Look, Caroline," Elena said, handing her the shoes, "I think you should know that Damon has kind of a reputation, and –"

"You don't have to say anymore, Elena. I talked to Matt at the Grill yesterday, and he kind of told me about that."

"Does it change your mind about tonight?"

Caroline shook her head, "No. I still want to go out with him." She fastened the shoes and then stood up, "What do you think?"

"I think you look good. C'mon, let's do your hair and makeup."

As Elena curled Caroline's hair and helped her put her make-up on, she chatted with her. They weren't talking about anything exactly; Elena was trying her hardest to get Caroline's mind off of how nervous she was. After her hair was curled, Elena helped her clip it up and then led her over to the mirror, "Well?"

"Wow," Caroline said. She took a deep breath, "I think I'm ready."

-x-

Damon pulled up to Caroline's house precisely at six o'clock. He figured that she was probably nervous, but he could take bets on how much more nervous he was. Now, Damon had never been nervous on a first date – no, he was always the smooth talker who knew what he wanted and how to get it – but this time it was different. He really liked Caroline and wanted more with her; he wanted a relationship with her.

God, a relationship. He hadn't wanted one of those since Katherine broke his heart six years ago. The bitch had stayed in his thoughts for a long time, and now that he was over her – which he had Caroline to thank – he had time to realize how badly he wanted one with Caroline. She wasn't just any girl. Because she was so special, he was pulling out all the tricks – flowers, candy, nice restaurant, a moonlit walk on the beach – because he wanted Caroline to know that she deserved romance just as much as anybody else.

He couldn't wrap his mind around the fact that Caroline thought she deserved to be treated the way that dickhead Lockwood treated her. Her life must've been pretty bad to feel like she deserved that, and that made Damon angry. Even when he was just sleeping with different girls, he would never ever treat them like they were property. Whoever made Caroline feel the way she did really twisted reality and made her feel worthless.

Damon got up to the front door and rang the bell. He was expecting Caroline to answer, but Elena opened the door.

"What are you doing here?"

"Caroline is my very best friend in the entire world and I was helping her get ready for her very first date." Elena may have said more than that, but Damon wasn't listening to her anymore. He watched as Caroline came down the stairs. She looked just like a princess. The dress, and the shoes, and her hair – she looked perfect.

"I'm going, now," Elena announced, getting Damon's attention once more. "I'm going to see if Stefan wants to catch a movie or something." She looked at Caroline, "Call me after your date."

Once Elena was gone, Damon handed Caroline a bouquet of flowers. Caroline almost melted when she saw them. They were tulips, her very favorite flower in the entire world.

"How did you know?" She asked him, taking the flowers and breathing them in. She went to the kitchen and put them in a vase with water as Damon followed her.

"Your mother. I called her last night."

"How did you get her number?" A confused look covered her face, "For that matter, how did you get mine?"

Damon laughed, "I ran into your mother at the coffee shop yesterday."

Smiling, Caroline rolled her eyes, "It figures. Well, you cheated."

Damon shrugged, "I'd cheat again, just to see that look on your face."

Caroline blushed, but started out the door, "Where are we going?"

"It's a surprise."

He escorted her to his car and then he got into the driver's seat. They drove for about ten minutes until they reached a very fancy restaurant.

"God, Damon, this can't be it. It takes months to get into this place, and the food costs a fortune."

"This is it, Caroline. This is where I'm taking you. I've got connections with the owner, I got us a reservation, and besides that, I can afford their food. It's not a big deal."

"I wasn't saying that you couldn't afford it, Damon. It's just that…well, I'm not that special."

Damon looked into her eyes, "Tonight, don't think. Ignore those standards that everybody set for you while you were in the system. This is different. I want to pamper you this way."

Caroline nodded, "I'll try."

They went inside, and were led to the best table in the house, which just happened to be on the patio, overlooking the beach. Caroline swooned; it was just so romantic. When they were seated, they had some light talk. Caroline was surprised that Damon didn't really talk about himself; he wanted to know more about her. He asked her questions, and listened carefully to her answers. Caroline talked about her life as a dressmaker and the wedding dress from hell.

"I just finished it," she said after their dinner arrived. "I call it the wedding dress from hell, because, honestly, it is. There is so much beadwork, which takes forever. I never imagined doing this much beadwork on a dress that I wasn't going to wear."

"I noticed that you make practically everything you wear," Damon observed. "It reminds me of the girl in the movie Enchanted."

Caroline giggled, "You watch Disney movies? Really?"

Damon shrugged, "I only know that because Elena made me watch it with her. If it had been anyone else, I would have told them to fuck off, but it was Elena, and she's practically a part of my family."

"Yeah," Caroline said thoughtfully. "Mine, too."

-x-

After dinner, Damon took Caroline to the beach, which was literally only a few feet away, and the first thing Caroline did was take off her shoes and wiggled her toes in the sand.

"Sorry," Caroline said, slipping the shoes off and held them in her hand, "I don't believe anyone should wear shoes unless they absolutely have to."

"You like being barefoot?"

Caroline giggled, "Yes, I do. I refuse to wear shoes unless it's absolutely necessary. When I get married, I'm getting married barefoot."

Damon laughed as they started to walk. All of the sudden, Damon got really serious and looked at her, "So, the other day I heard Elena say that you've been in love twice. I know one of them was dick – I mean, Tyler Lockwood. Who was the other?

Caroline hesitated for a moment, so Damon said, "How about this? I'll tell you something about me if you tell me something about you. We can share."

Caroline shrugged, "I guess that's fair. You go first."

Damon thought for a moment, "There was this girl. Her name was Katherine, and she was pretty, and fierce, and had real fire to her. She was independent of practically everybody and when she wanted something, she went for it. Sometimes she was really in your face about things, but that just added to her charm. I loved her. I really did, and I could've spent my entire life loving her, but instead, she thought it'd be more fun to play me against my brother. She thought that she could have us both. I was so stupid, I fell for it, and I started to blame Stefan, when, in truth, it was all Katherine. She was a manipulative bitch and she left my heart in pieces."

Caroline nodded, "I'm sorry, Damon."

He shrugged, "It happened almost six years ago. I'm getting over it. So, now it's your turn."

"His name was Mike Jones." She sighed. "He was the son of my first foster family. He was nineteen when I was fourteen. I didn't mean to fall in love with him, it just kind of…well, it just kind of happened. We started out as fuck buddies. That's all that it was, and he made it very clear that's all he wanted, and I was okay with that. I was so naïve, so very stupid. It went on for about a year and half, until I thought I was pregnant." She started to stare into space, "I remember his words when I told him. He said, 'Do whatever you want. Kill it, put it up for adoption, keep it, I don't fucking care. But you can never tell anybody it's mine."

Damon clenched up his fists; he couldn't believe what he was hearing. He didn't want to show too much emotion, though, since it was their first date and he didn't want to come on too strong.

"I was so sure, but I was wrong. Anyway, my foster parents found out about it and they turned against me. I had to come clean, especially since the bastard gave me an STD." A worried look came over her face as she looked at Damon, "Don't worry, it was curable. I'm clean now. I get tested every year, just to make sure. But anyway, he denied everything and made me out to look like a lying whore. I was so stupid, so naïve, and I thought that he cared about me, so I lied about stuff, changing my story so he didn't look guilty. I did it to protect him. By the end of my time with that family, they had taken practically everything away from me, beat me, and made me hate myself. They made me out to be a slut, even telling me that I deserved that STD. If I could go back, I'd turn the son of a bitch in, first thing, but I loved him. I don't know why, I thought that I loved him. Now, as I'm older and wiser, I wonder if I really did, or if I just thought I did, but anyways, I was convinced that he loved me back. It turns out that he's still victimizing young girls, just like he did me."

They stopped walking and Damon turned to look at her, "You feel guilty."

"Yes," she whispered, tears starting to fall down her cheeks. "I do."

He brought his hand up and wiped away her tears, "It's not your fault, Caroline. You didn't do anything wrong. You didn't make him hurt you, and you didn't make him hurt those other girls, did you?"

She shook her head.

"That stuff they said, that was all bullshit. I know they probably beat it into you, but listen to me," he said, his hand still cupping her face. She looked at him, "You were the child. He was the adult. He should've acted like the goddamn adult instead of fucking with your head the way that he did. And as far as that family goes, the way they treated you was wrong. You were the child, you were the victim. It's not your fault."

"Nik and Elena have been trying to tell me that for the last eight years. Just because they say it doesn't make it true."

"Have you ever wondered, Caroline, if maybe you're the one that's wrong?" Damon asked gently. Caroline looked up into his eyes.

"What do you mean?"

"Well, it's just that Klaus and Elena seem to be pretty smart. Hell, I've known Elena her entire life. But if they both think the same thing, then –"

Caroline sighed, "Maybe they're just biased."

"I don't think they are," Damon said, watching her carefully. "The more people that say that something is true, then the more likely it is."