Author's Note: Man, this chapter has been a bitch to write. Nothing seemed to stick. I just could not get the words out. I tried Elena's POV then Damon's and then back to Elena's before anything really came out. Then, like a wall broke, everything just came pouring out today. So, this chapter is pretty long, but I hope you all will like it. Thank you for all of the reviews. I hope you all enjoy it! Read and review!

Chapter 4

Baby, don't move at all
Cause you're about to break my fall

Twenty minutes later, the taxi driver finally pulled up to the curb for Departures at JFK. After a quick apology for the traffic and helping her get her bag out of the trunk, she paid him and sent him on his way. Now, she was staring up at the numerous screens for Departures. She was here and had all of the options in front of her; she just needed to make a decision.

She felt like she was always making some life altering decision. Her whole life was made up of one grand decision after the other. Every time, she'd spend what felt like months agonizing over her decision, only to have one eye opening moment where everything made perfect sense. She'd have some moment of clarity and it was like the answer had been staring her in the face the whole time, she'd just been too blind to see it.

She needed one of those moments of clarity right now. She needed to be able to pick out a destination from one of the screens in front of her, and go with it. Nothing seemed right though. There wasn't anywhere she wanted to go but back to that hotel room and see Damon. She wanted him to tell her that he did love her and he did want to be with her, but if he hadn't done it when she went, he wouldn't change his mind now.

Damon had a very clear outlook on break ups: no matter how much it sucks, when it stops working, you end it. In his mind, they stopped working the second she left for Chicago. She'd pulled the plug and he wasn't going to put it back in.


"So you're on a break?" Caroline questioned, her eyebrows knitted together in confusion.

"Something like that," Elena mumbled as she ran her fingers over one of the discarded wedding gowns in the small dressing room.

She, Caroline, and Bonnie had come dress shopping today, and while the dress consultant was picking out more options for Caroline, she took the opportunity to jump on Elena. The engagement party had been two weeks ago, and her and Matt were barely hanging on by a thread. They were hardly even speaking to each other, and the few times that they had, the conversations had deteriorated rapidly into screaming matches. Last night, he decided they needed time apart for him to think and her to "get the crazy under control".

"Who are you, Ross and Rachel?" Caroline teased.

"More than you think." It was now Bonnie's turn to speak up and throw her thoughts into the fire. "Matt just doesn't know he has anyone to be jealous of."

Elena groaned, knowing her chances of keeping Caroline in the dark about her kiss with Damon were completely shot to hell now. After two weeks, she'd begun to think that she was going to be able to escape this without Caroline knowing. She was feeling enough guilt and confusion over the kiss inside of her own head. She didn't even want to know what she would be feeling once she actually had to talk about it, especially with Caroline, who still hadn't agreed to let Damon back in the wedding.

"What is that supposed to mean?" Caroline's eyes latched onto Elena's nervous gaze through the mirror. "Why would Matt be jealous?"

"Ask Elena."

"Nice," she snapped at Bonnie, who was more than content to throw her in front of a moving bus and leave her there.

"One of you needs to start talking." Caroline's eyes darted between her two friends, waiting for someone fill her in on what was going on. "I don't care who says it, but one of you better spill."

Elena crossed her arms over her chest and shook her head. "I'm not saying anything." Her mouth was plastered shut. If Bonnie wanted to tell Caroline about what she walked in on that night it was up to her, but she wasn't about to come clean just yet.

Bonnie watched Elena, waiting for her to say something, but when it became clear she really wasn't going to tell Caroline, she turned to the blonde and said, "Elena kissed Damon the night of your engagement party."

"Elena did what?" Elena cringed as Caroline whipped around on the pedestal. She held tightly to the chest of the wedding dress she was trying on as the skirt whipped around her tiny body when she spun around to face Elena and Bonnie. Her bright blue eyes darted between her two friends, waiting for an answer. "You do not just drop that bomb on me and stop talking!"

"You're just on a roll," Elena mumbled beneath her breath as she glared at Bonnie.

"Tell me she's wrong," Caroline demanded. "Tell me that you, Elena Gilbert, Matt's girlfriend of four years, did not kiss Damon."

She groaned and rolled her eyes, knowing that her back was pressed against the wall. The cat was out of the bag now. She had to tell Caroline everything. "I was upset and I'd been drinking, and he was really nice."

"Yeah, cause he wanted to get in your pants," Caroline scoffed.

"But I don't think he was," she argued. He hadn't been flirtatious with her that night, nothing like compared to the other times they'd been around each other. He didn't do his weird little eye thing that she'd come to associate with him. He was just nice and honest.

"Stefan is nice to you and you don't go around kissing him."

"I feel bad enough, okay?" she snapped, agitated with what Caroline was implying. In four years, she had never cheated on Matt, never even gotten close. She'd always been loyal to him, and now she felt horrible. He trusted her, and she'd broken that, even if he didn't know it.

"Why would you kiss him? I mean, Damon, of all people? Really, Elena?" Caroline seemed so utterly flabbergasted by the thought that Elena would even give a second glance to Damon. It was as if she couldn't fathom that she'd actually like him as a human being, and not judge him for some of his questionable decisions of late. Granted, she'd never actually seen his very good decisions, but she knew that there was something good inside of him. Even if their entire conversation was an act on his part to sleep with her, she'd still heard his fight with Katherine, and knew that there was more to him than met the eye.

"If you were going to drop the bomb, you could have at least given her the prelude to it all," Elena snapped in Bonnie's direction before looking back at Caroline. "What Bonnie failed to mention, is that Matt told her that he didn't see himself marrying me. A fact I didn't know until that night. I had been perfectly oblivious to the fact that while I believed we were okay, he was trying to figure out when to break up with me. That's why I was upset that night. That's why I drank. And that's why I ended up by that pool, talking to Damon."

Caroline was about to open her mouth and offer another counter argument, when the sales attendant entered the dressing room that they were in for Caroline's search of a wedding gown. "I've brought in a few more options for you." The attendant was soft-spoken as she reentered the room, and Elena feared that she had never had a client quite like Caroline Forbes before.

"I hope they're dramatic." Caroline smiled as she attempted to get a glimpse of the dresses the woman was holding. Her admiration of the dresses only lasted for a few short moments before she continued on with the conversation like they were still alone. "You and Matt fight all the time and you don't make out with guys. I don't get why you'd make out with Damon. Especially after that speech he gave."

"Well, it's not like I was feeling that great about relationships that night either, so I might have understood where he was coming from." At Caroline's furious glare in the mirror, she quickly added, "However, it was completely inappropriate and wrong." She waited for Caroline's face to relax before she continued. "Why is it so hard to believe that we just had a nice conversation, and things just spiraled? One minute he was wiping eyeliner off my face, and the next we were kissing."

It had all started so innocent. She hadn't been able to wipe the eyeliner off without a mirror, so he'd helped her. Then, his eyes locked on hers and it was like they were sucked into another world. All thoughts of right and wrong fell away in that moment. She wasn't the Elena that was upset over the possible ending of her four-year relationship. She wasn't the Elena that couldn't seem to figure out how to move her life forward. She was just the Elena that wanted to kiss Damon in that moment, so she did.

Then, Bonnie came outside and she came crashing back down to earth, where she was very much in a relationship, and he was going through a very nasty divorce. Once she went inside, Bonnie had lectured her until they found Matt, unable to figure out what was going on in Elena's head. Bonnie lived in a world of black and white. There were no shades of grey with her. To her, it was simple; if she wasn't completely happy with Matt then she needed to end it. That's why she needed Caroline on her side with this. If either of her best friends would understand, Caroline would be the one that would come closest.

Things with Matt were in a complete limbo and she didn't even know which way was up or down anymore. She just knew that she loved him, but it didn't seem to be enough. She didn't know if she was ready to throw in the towel yet on their relationship, but she didn't know if she could take that plunge and move in with him.

Thoughts like that were what had gotten her into this mess to begin with. She'd been selfish during the past year, only thinking of what she really wanted. She hadn't given Matt a real option in how their relationship would be. It was really only a matter of time before he decided he was going to have one. They were ultimately at a stalemate.

"Fine, let me see if I can figure this out," Caroline sighed like this was the hardest thing she was ever going to have to say in her life. "You were upset because of Matt, so you kissed Damon, and now you and Matt are on a break. Am I close?"

"Pretty much."

"Do you like Damon?" Caroline cringed as she said the words.

Elena froze, unable to answer the question. In all of her guilt ridden thoughts of that kiss with Damon she never stopped to ask herself how she felt about him, or if she felt anything at all. Her brain had been so focused on the mere fact that she'd betrayed Matt. She hadn't allowed herself to thing beyond the fact that she had wanted to kiss him. If she let herself think about it, she was scared of what conclusion she would come to.

Her feelings about Matt and their relationship were confusing enough without adding Damon into the equation. So, it left her at a loss for words as Caroline and Bonnie stared at her, waiting anxiously for her answer. "I don't know," she confessed quietly, embarrassed with her inability to find a real answer. She had a boyfriend and she'd kissed another man without any thought of the repercussions for her actions. She hadn't thought about how it would hurt Matt. He hadn't even been a thought for her in that moment. And now, two weeks later She still didn't even have a good explanation for it.

"How do you not know?" Bonnie asked, clearly confused. She wished things were as simple for her as they seemed to be for Bonnie. If she held as steadfast to her morals and beliefs as Bonnie did, her life might not be in this place right now.

"I don't know. Everything with Matt has my brain so jumbled I don't know what I feel about anything anymore. All I know is that I love him, but I don't know what to do with that anymore."

As Elena's voice wavered with emotion, Bonnie reached out and ran a comforting hand down her arm. For her harsh reactions sometimes, she was never anything short of supporting.

"Maybe it's time to let him go," Caroline spoke up, her voice gentle and cautious. It was a fine line to dole out relationship advice to a friend. If you advised the friend to end the relationship and she didn't, there was tension for saying it. However, if you advised your friend to stay in a relationship and she didn't, there was tension for encouraging a doomed relationship. There was always the chance that the advice could backfire, but if anyone would give her honest opinion, it would be Caroline. "Right now, you're just treading water and making each other miserable. That's not good for anyone. And if you're going around kissing Damon, I think that speaks to a problem in the relationship that you're not admitting."

"Oh my god," Elena gasped quietly, shock and awe filling her. As the consultant tightened the dress on Caroline, all conversation and thoughts of anything else went out the window. All three women were captivated as they took in the vision in white that reflected in the mirror. The confusion and guilt didn't matter anymore. They'd found the dress.

Caroline's tearful gaze roamed over her appearance in the mirror. Her hands were shaking as she ran her hands over the soft silk of the dress. "This is it," she choked out. "This is the dress."

Bonnie and Elena couldn't take their eyes off of Caroline as they mutely nodded their heads.

That was the dress.

It was daring and bold, demanding nothing less than the full attention of everyone in the room. The dramatic floral detail along the bust gave way into yards of silk that draped softly down to the floor. In short, it was Caroline in every way possible.

After several minutes of the women staring at Caroline in shock, Elena finally found her voice to say, "Stefan is going die when he sees you in that."

A beaming smile blossomed over Caroline's face. "He is, isn't he?"

"I don't think he'll last long enough for the minister to pronounce that he can kiss the bride," Bonnie agreed with Elena. "Caroline, he is going to lose it."

The blonde hopped up and down giddily on the platform, clapping her hands together. "I found a dress!" she exclaimed excitedly. "I'm getting married!"

Elena smiled brightly at Caroline's utter elation over the thought of having found her dress. Her best friend had dreamed of this moment her entire life. When they were children, Caroline would keep them up until the early hours of the morning, mooning over finding her prince charming and getting married one day. They'd spent so many hours imagining this day, and it was finally here.

Two years ago, Caroline set eyes on Stefan Salvatore in the back of her English class and she'd been done. All of their mindless talks of finding a husband suddenly formed into a reality. She never stopped to wonder if Stefan was it. He had her from the very first time he kissed her, and she'd never looked back.

The realization pulled tears to her eyes as she watched Caroline and Bonnie hug. She realized that she never had that with Matt. There was love and comfort, but there had never been the heart wrenching desire to never leave his side. She didn't look at Matt and feel glee over their future like Caroline did with Stefan. She looked at him and felt fear over what would happen if she gave into that future.

In a small dressing room nestled into the heart of a Manhattan bridal shop, Elena realized that there wasn't really any confusion about what she felt for Matt. The confusion was about what she didn't feel and why she didn't feel it. As the silent tears slipped down her cheeks that she masked with a shaky smile, she felt her heart breaking inside for what she now understood. Matt was never going to be the one. She was never going to wake up one morning and know that she was ready.

If she were, the kiss with Damon never would have happened. If Matt was the one, she wouldn't have poured her heart out to a man she barely knew instead of the man that had been by her side for four years. If Matt were the one, she wouldn't have to wonder, she would already know.

This crippling thought stayed with Elena for the rest of the day. It followed her through Caroline's purchase of the dress. It followed her through her trip to buy groceries for her apartment. And it had followed her to work, where she was now, hauling in a box of vodka from the storage as she prepared for the bar to open in an hour.

As if a signal had gone out that something had changed inside of her head, or more so clicked into place, Matt had been calling her all day. Her phone had been ringing nonstop since she got to the bar. Every time she looked down and saw that it was Matt calling, she ignored the call. She wasn't ready to talk to him yet. She didn't know what she was going to say or how she would even say it once she could figure out the words. So she avoided him, like she always did when she wasn't ready to face something.

Elena's phone rang for what felt like the one-hundredth time in the past few hours. This time, she didn't bother to look down to see Matt's name staring back at her once again. She pressed the ignore button and went about drying the glass in her hand. She wouldn't avoid him forever, just for now. That was what she was telling herself at least.

"Now that's just cold." Elena gasped at the unexpected voice, her head shooting up to see Damon sauntering into the bar, a teasing smirk on his face and a bottle of scotch in his hands. "I come all the way across town to see you, only to find out you are ignoring my calls. That hurts, Elena."

Her racing heart soon began to settle once she realized it wasn't some complete stranger who had wandered in off the street. Then her heart began racing again, because it wasn't a stranger who had wandered in off the street, it was Damon. "What are you doing here?"

He slid onto a bar stool, not phased in the slightest by her accusatory question. "Why are you ignoring my calls?"

She set the glass in her hands down on the bar. "I thought you were somebody else."

"Now I'm intrigued." He set the bottle of scotch down on the bar and pushed it toward her. "I'd like a scotch on the rocks."

Slightly amused, Elena picked up the bottle and stared down at the expensive brand. "You brought your own scotch to a bar?"

"My tastes are a little more refined than what you offer here."

Knowing there was no point in trying to deny it, she went about pouring him a glass of the aged alcohol. "So, what exactly are you doing here?"

"Blondie still hasn't let me back in the wedding, so I told Stefan that I would be on my best behavior to convince Caroline to let me be best man again." His voice was casual as he tried to play it all off as a joke, but she could see that he underneath it all, he might actually be worried about it.

She tossed the towel she was holding down and leaned onto the bar. "Where do I come into this whole best behavior thing?"

"For starters, we can start planning the bachelor and bachelorette party. For another, you can try to avoid any mention of the fact that we kissed, at least until after the wedding." She cringed at the mention of the kiss, and he quickly jumped on the look. "Let me guess, she already knows."

"If it helps, I wasn't the one who told her. I didn't want her to know either."

He pondered over this bit of information for a moment as he sipped on his scotch. After a moment he looked at her and asked, "On a scale of one to Caroline, how mad is she?"

"Actually, she's not really mad. She was confused, but I don't think it really has to do with you so much as me."

This seemed to capture his full attention. "What do you have to do with it? I thought Caroline would think I practically forced myself onto you."

"Okay," Elena finally conceded with a small smile. "So she might have initially blamed you."

"Why doesn't she now?"

"Maybe she realizes that I'm not 12 and you can't manipulate me?" she questioned with a raised eyebrow. "And maybe she knows that I wouldn't kiss you unless there was something else going on." Damon opened his mouth to say something, but Elena quickly cut him off. "Why don't we talk about Las Vegas? The bar opens soon, so we should probably focus on the important things."

"But it's so fun," Damon taunted with a grin, but it wasn't easy and comfortable like that night at the pool. Suddenly, the gentle ease with which they'd talked that night was gone. Her stomach was aflutter with something akin to butterflies that she couldn't quite figure out. He was looking at her with a teasing smile, but it didn't feel teasing or lighthearted. It felt like he was searching for something.

"I have a boyfriend," Elena finally reminded him, although she was also maybe reminding herself. She couldn't focus on the kiss. She had to focus on Matt and how she was going to handle everything with him, and Damon being here did not help with that. She didn't know how he could act so casual about it when she'd just seen that he was genuinely worried about not being allowed back in his brother's wedding. For everything Caroline said about Damon, she always acknowledged that he had a deep affection for his younger brother. He should be focused on making sure he got back in the wedding, not on their kiss.

"Oh, is that still going on?" Damon smirked with feigned surprise. "I would have thought that was over the night you stormed out of the engagement party crying."

Annoyed, she snapped, "It's a four-year relationship. You don't just end it because things are going a little rough." In reality, she knew that that was exactly what she was going to do soon. Tonight or tomorrow or a few days from now, her relationship with Matt would be over. She wasn't ready to acknowledge it out loud though, especially not to Damon, who she still barely knew, despite the kiss they shared.

"That's exactly what you do. Once the relationship stops working, you pull the plug."

"Like you and Katherine?" she countered.

Damon's eyes hardened at the mention of his ongoing divorce. "What is that supposed to mean?"

"It means that Caroline is my best friend, and she's always talking about how you and Katherine can never really pull the plug. She says the two of you fight over everything in the divorce settlement just so you don't actually have to sign the divorce papers."

"Now why on earth would I do that?" he asked, like he couldn't possibly think of a reason why he would ever engage in such tactics.

"Because she's your wife and you love her, and according to Caroline, in some twisted, messed up way, Katherine actually loves you too."

Damon's clear blue eyes penetrated her gaze, and she found that she couldn't look away. She'd hit a nerve inside of him, said something she probably shouldn't have, but he was just staring at her, completely silent. There was something unnerving about it all. She felt as if he was seeing straight through what she was saying and down to what she really meant.

Her phone suddenly sprang to life and Elena reluctantly broke her gaze to glance down to see Matt's name flashing in front of her. Before she could press ignore Damon's hand snatched her phone up and pressed answer. "Elena Gilbert's phone." Panicked, she desperately reached out for her phone and tried to pull it from him, but he easily evaded her attempts. "Who may I ask is calling?" he paused for a moment before continuing, "Matt? The name isn't ringing any bells. Are you sure you don't have the wrong Elena?"

"Give me the damn phone," she hissed at him, still trying to snatch it away from him.

"I'm the guy that's with Elena. Who are you?"

With all the effort she had, she practically launched herself onto the bar and ripped her phone from Damon's hand. "Matt?" she called out when she jumped back down to the floor. "Are you there?"

"Who the hell is that, Elena?" Matt shouted at her.

"It's nobody," she quickly explained, flashing angry eyes on Damon. "Just some guy being a dick."

"I've been trying to get you all day and finally this guy answers and says that he's with you. What the hell is going on?"

"Look, it's just Stefan's brother, okay? He answered the phone before I could stop him."

"Why are you even with Stefan's brother? He's not even in the wedding."

"I'm at the bar and he came to talk about the bachelor and bachelorette party. It's nothing, I promise."

"Whatever," Matt sighed, clearly still irritated. "You're obviously busy, so just call me later." Before she could say anything, he hung up, leaving her staring down at her phone wondering what in the hell had just happened.

After the shock wore off, she looked up at Damon, livid with what he'd done. "That was a dick move."

Damon shrugged and stood up from his stool. "I've been told I tend to make a lot of those."

She picked up his bottle of scotch and shoved it at him. "I think you need to leave. I have work I need to do."

"Yes, I'll let you get back to your busy schedule. You obviously have your hands full with your boyfriend, so I'll handle things with Las Vegas."" He pulled a few 20s out of his wallet and threw them onto the bar even though he hadn't actually purchased any alcohol. "By the way, that inability you say I have to pull the plug on my marriage? Mediation ended today. Maybe next time you should consult your facts before you listen to everything Caroline has to say."

As she watched Damon walk away she felt remorse over what she'd just said to him. It hadn't been her place to say what she had about his marriage. "Damon, wait!" she called out to him before he could get out the door. She ran around from behind the bar and rushed over to him. "I'm sorry," she apologized when she ran in front of him to block his path. "I shouldn't have said that. My situation with Matt is different. It would be concerning if you thought it was easy to end your marriage."

"There's no need to apologize," he told her, his voice tight. The muscle in his jaw twitched as he looked down at her. "Are you going to move or do I have to move you?"

She tried to find something – anything to say to pull her foot out of her mouth and fix this situation, but she didn't know what to say. His marriage was one step closer to being over after today, and she'd just told him that he'd been too scared to do it. It was a line she shouldn't have crossed, and she felt horrible. Before she could think through what she was saying, she'd blurted out, "Have dinner with me."

His eyes widened a fraction of an inch as he stared back at her. "Excuse me?"

"I just ungracefully put my mouth where it didn't belong."

"So why does that translate to dinner? I don't need a pity date."

"It's not a date and it's not out of pity," she quickly corrected him. "Besides, we really do need to figure out everything with Las Vegas. So, dinner?"

"Why should I say yes?"

"Okay, now you're just being obnoxious. Do you want a free dinner or not?" She might feel bad for what she'd said, but she wasn't going to beg.

"What about your job?"

"Mark will be here in 20 minutes. He can hold down the fort for a few hours."

He seemed to contemplate her answer for a few moments, before finally nodding his head. "Fine, you've talked me into it."

A smile broke out across her face and she released a relieved sigh. "Good, just let me leave Mark a note, and we can leave." She rushed over to the bar, where she pulled a piece of paper and a pen from her purse. She scribbled out a short note explaining that she would be back soon, and she'd give him half of her tips that she made after she got back. Once she grabbed the keys and her purse she turned off all the lights and walked back over to Damon. "Okay, let's get out of here."

He held the door open for her and as she passed by him he said, "You better not take me someplace crappy. Katherine is walking away with my house and 20 million dollars."

"Jesus," she gasped, practically dropping the keys from her fingers. "Who the hell walks away with that much money from a divorce?"

"My wife."

She looked up at him as they began walking. "I really am sorry about your divorce. It can't be easy."

Damon groaned and rolled his eyes. "If we're going to talk about my divorce the whole time, I'm going to turn around right now and go home, while I still have one."

Catching on that he didn't want to talk about Katherine, she held up her hands in surrender. "No more divorce talk. In fact, I won't even say the word. It doesn't exist."

"I like where your head is at." As they came to a corner, Damon looked around, clearly unfamiliar with this part of town. "So, where are we going? I have no idea what's around here."

"Well, there's this trendy little dumpster down that alley over there," she began with a light chuckle. "You act like I'm leading you into the valley of death or something. There's actually a really good Thai restaurant two blocks down."

Soon, they were nestled into a corner booth at one of her favorite restaurants by her work. She was happy to find that things were returning to how they had been the other night by the pool. All divorce talk had ceased since she banned the word, and they were actually enjoying a lighthearted conversation about Stefan.

"He thought he was going to keep it hidden under his bed and nobody would ever notice. I caught him trying to take it for a walk in the middle of the night, in his Spider Man pajamas and rain boots."

She laughed at the mental picture of a little Stefan trying to sneak out of his house in the middle of the night. "He just wanted to help a puppy."

"It belonged to the family on the 15th floor," he exclaimed a little too loudly. When he got more than one annoyed glare from a few of the patrons he lowered his voice and leaned closer to her. Apparently, he found out that some cultures eat dogs as a delicacy, so he started thinking anyone who owned a dog was going to eat it for dinner."

"He did not!"

"Yes, he did," Damon insisted, still smiling. "And so he wouldn't get in trouble, I had to sneak the dog back down to the 15th floor, where I knocked on the owner's door and then ran up to the next floor before taking the elevator back up to our penthouse." He swallowed the remaining contents of his beverage, setting the empty glass on the table in front of him. "He may be smart now, but the kid was not bright."

"You really do love him," she said in soft wonderment, never seeing the depths of it until now. She could hear it in his voice when he talked about Stefan, and even though he did his fair share to make his brother mad, he really did love him.

Damon tilted his head, confused by her observation. "I might pick on him incessantly, but he's still my baby brother."

"I know, it's just, hearing you talk about him and how you talk about everyone else, you're different. That's all I meant."

A shadow crossed over Damon's features and he leaned back in his seat, putting distance between them again. "I know my reputation and that I've more than earned it, but Stefan is Stefan. Caroline can say what she wants, but he's my brother. He's all I have."

"Don't you work for your father?"

"That's different. Surely you have a vastly different relationship with your parents than you do with your sibling."

Elena's throat constricted at the mention of her parents. All these years later it still hurt when she thought about them and how she'd never see them again. She may have made peace with her parents' deaths, but it didn't make the pain go away. "They're dead."

His tapping fingers stilled immediately on the table. "I'm sorry. Caroline had never said anything."

"It's fine," she quickly tried to assure him. "It was 5 years ago, so it's been a while."

"But they were still your parents."

At the distance in his voice, she remembered Caroline telling her that Stefan's mom died when he was just a child. She knew that Damon understood her sense of loss. "How old were you when your mom died?"

He glanced down at the table when he answered her. "I was 12." Before she could talk herself out of it, she reached her hand across the table and gently squeezed his hand. His head quickly shot up at the gesture, his eyes slightly wide with shock. "We knew that it was coming, so I got to say goodbye and all of that stuff that doesn't really make a difference in the end."

The short moment was interrupted as the waitress approached their table, a pad and pen poised in her hands. "Are you ready to order?"

Damon looked down at the menu he had yet to open and then back at Elena. "Since you picked the place, you can pick the food. I am deferring to your expertise."

"That's a dangerous choice," she warned with a small smile before she looked up at the waitress. "We'll have the Yellow Curry."

The waitress quickly copied down the order and retrieved their menus, her eyes lingering a few moments too long on Damon. "Your order will be ready shortly."

Elena watched the waitress walk away before looking back at Damon. "She thinks you're hot."

Damon smirked and wiggled his eyebrows. "Most women do." She rolled her eyes and shook her head, but she couldn't keep herself from smiling. "Don't give me that look. You got checked out at least five times on our way here. You can't tell me your ego isn't stroked by the male sex's appreciation of your looks."

"Are you saying I'm hot?" she teased.

"Damn straight. You are sexy and you know it."

A blush crept over Elena's cheeks at Damon's compliment. She knew that she was attractive. She got hit on by plenty of men at work, but something about hearing Damon say he thought she was attractive made her giddy. He was married to a model, and she was just a bartender that walked around in cheap clothes, but he thought she was sexy. It was flattering and slightly embarrassing at the same time.

"Well, thank you for the compliment."

"Just calling it like I see it." To her surprise, he gave her a few moments to get her blushing under control before he continued their conversation. "So, how in the world did all three of you girls end up in New York?"

Elena shrugged her shoulders before answering, "Caroline wanted to study fashion at NYU. I wanted to study writing at Columbia, and Caroline didn't really give Bonnie an option. We've never gone more than a week without seeing each other since we were 6. We just couldn't stand to go separate ways."

"You three make an interesting group."

"I know we're different, but they're my best friends and they never judge me, no matter what."

Damon swirled the ice around in his drink as he pondered over his next words. "I guess that comes in handy when I'm involved. I'm sure I bring out the knee jerk reaction to judge."

"You bring out something."

"Clever."

Elena's phone beeped, notifying her of a new text. She picked up her phone from the table and her throat went dry as she read the message from Matt. So much for being at the bar. "Crap," she groaned.

"What? Caroline having a wedding crisis?"

She dropped her phone back to the table, at a loss for what she could say back to him. No matter what she said he was going to be mad at her. "Matt went to the bar."

Damon cringed. "Yeah, that's probably my fault. Sorry."

"I'm the one who keeps lying to him."

"I'm assuming he doesn't know about the kiss?"

"God no,!" she exclaimed. "Our problems are big enough without adding that into it. If he found out, he'd hate me. We're already going to have a bad breakup as it is."

"What happened to not giving up when things get a little rough?" he questioned.

She knew he was throwing her earlier words back in her face, and she figured she brought that one on herself. "If I tell you this, do you promise to not make fun of me for it or call me a stupid girl?"

"I don't know, depends on what it is." She narrowed her eyes to glare at him. "Alright, I won't pick on you if you tell me."

Elena looked down at her phone again before looking back up at Damon. "From the moment your brother kissed Caroline, she was a goner. From the very beginning, he was it for her. There were no doubts or fears. She just knew, and the truth is that I've never truly known with Matt. Things have always been so easy, so I just thought it meant we were supposed to be together forever, but it's not. When I think about marrying him it scares me because I'm scared that I'll lose who I am, because I'm just not ready. And if I'm not ready by now, then I'm never going to be ready." She averted her gaze downward as she felt the onslaught of tears coming. "God, I can't believe I'm doing this again around you."

This time it was Damon that reached out and grabbed her hand in a soft moment of reassurance. "Break ups aren't easy, especially when you thought you'd spend the rest of your life with someone."

"How do you do it? Even when you know you have to, how do you end it?" She wiped her face before looking up at him again.

"I don't think you should take advice from me on how to end a relationship." At her continued questioning gaze, he softly explained, "I handed Katherine divorce papers in bed."

"When you woke up one morning?" she asked, almost scared of the answer.

"No, I wasn't that kind. I had sex with her, got out of bed, grabbed a suitcase of hers that I'd packed, handed it to her along with the divorce papers, and told her to get out."

"I'll put that down on my 'How to Not Break Up With Matt' list."

"That's probably wise," he advised her, but then his face turned serious. "There's no right way to end a relationship, especially not one that's lasted for so long. All you can do is tell him that you can't be with him. Whether you're gentle or not is up to you, but either way it's going to suck."

As Damon imparted his advice on her, she wondered how this could be the same man that had stolen her phone from her earlier and purposely made problems between her and Matt. He'd do things like that and say horrible things that he shouldn't, but then he'd say things like this. He'd reach across the table and grab her hand because she was upset. She rarely saw him be nice to anyone. What was so different about her?

"Why are you so nice to me?" she blurted out, unable to stop herself.

He narrowed his eyes in confusion. "Am I not supposed to be?"

"You're not even nice to Caroline most of the time. So, why are you nice to me? I sit here and I cry on you and whine about my relationship. I'm barely nice to me right now."

"Well, when you get past your poor choice in friends, you're actually not the worst company in the world. I know I'm a little self-absorbed but I haven't been clueless these past couple months. You somehow manage to stay calm around Caroline when she's having her fifth wedding meltdown of the night. You work your ass off in a job that I wouldn't survive a night in. Your sense of humor is actually on point most of the time, and you actually talk to me."

"Why wouldn't I?"

"Most women just flirt or try to figure out the quickest way into my wallet. I'm the hot bachelor to land now that I'm on the market again, but no one actually has a conversation with me, and if they tried, they probably couldn't even hold one, but you can. So, what I'm getting at is, you're a decent person, Elena Gilbert."

"Even if I made out with you while I have a boyfriend?"

The corner of his mouth pulled up toward a smirk. "I have no reason to file any complaints about your morals that night."

She smiled at his words. "You know what, Damon? You're not so bad yourself." She leaned forward and pressed a quick kiss on his cheek as the waitress approached their table with their dinner. "Now, let's get some food in you before you're tossed out on the street and left begging for money in Central Park."