AN: Thank you for the reviews on the last chapter. I think I've gotten back to all of you. I love hearing your thoughts and feelings on everything so far. I really was nervous about it, but now that I'm over that, I can get into the story and some explanations. We will now be delving into flashbacks. Since the flashbacks will be taking up most of the chapters, I really don't want to have them in italics, so I am just going to do a dividing line right now. The line will divide the present from the past. That might have to change at some point down the line, but if it does, I will give you all a warning. Anyway, here is the first chapter. I hope you all enjoy it! Reviews are always amazing!

Chapter 1

Waiting for Now
Don't ask me who I am
Don't ask me where I stand
Don't ask me what's my plan
Cause I don't know

Elena glanced around the city as it passed by her, the streets crowded with tourists and jaded New Yorkers. At 18 years old, she'd been in complete awe of New York City. Coming from a small town in Virginia, this place had been like a completely different world. She came with her two best friends and a million and one dreams. For a while, those dreams had begun to come true.

As a freshman at Columbia, she met Matt Donovan, and he quickly became her first real love, the first adult relationship she'd ever had. For four years she believed that he was the one, that she would spend her life with him, but the problems mounted and the distance began to grow between them. Then, one night in July, she spotted Damon across the bar and her world was forever changed.

"We're getting married!" Elena looked up as Caroline Forbes came rushing into the bar, flashing the diamond ring that had taken up shop on her left hand. Heads turned in the bar as she ran through the crowd, an elated smile on her face.

Elena couldn't help the girly scream that fell from her mouth, and she rushed around the side of the bar to wrap her arms around Caroline. "Congratulations!" she told her best friend, hugging her tightly before pulling back and grabbing at her left hand. "So, how'd he do it?" She'd gone with Stefan to pick the ring out weeks ago, but she still wanted to see how it looked on Caroline's dainty finger. It was large and gave off enough sparkle to catch the eye of a blind person.

"He took me to Central Park, and at first I was mad, because these heels are too high to walk in." She pointed down to her stilettos that looked far too uncomfortable for Elena to ever dream of wearing for an extended period of time. "But then I realized that we were where we kissed for the first time, when he was taking me home cause I was drunk and he didn't want me to go alone." Caroline got misty-eyed thinking about her first kiss she had shared with Stefan. "And then he told me he loved me and got down on one knee and then I cried and said yes."

"You're getting married," she told her excitedly, overcome with joy for one of her best friends, even if her own life was in complete turmoil right now.

"I'm getting married!" She exclaimed, the infectious smile taking over her face once again.

"Okay," Elena smiled, giving Caroline a brief hug. "I have to get back to work, but you get free drinks all night. Get your man over here to celebrate."

She got back behind the bar she'd been tending since her sophomore year at Columbia. It had started out as a way to make some extra cash to get her through college, and now, freshly graduated, it was quickly becoming the fallback plan as she decided whether she had the guts to really chase her dream or not.

From the moment her mother gave her a journal at 10 years old, she'd wanted to be a writer. She loved putting her thoughts into words on a piece of paper in front of her, and she loved creating stories that wove just enough of her life in to words that made it feel cathartic, while still leaving her a secret that only she knew. Then her parents died and everything changed.

For a while, she clung to that dream, desperate to feel closer to her mother. She'd somehow believed that it kept a part of her mother alive, but not too long after she started college, she began to question if the dream was still there. She stayed in school and completed her major, but the passion began to fade. The questions consumed her, and soon, her plans of getting her Masters were put on hold.

She'd graduated two months ago and the plans were still on hold. The deadline had long past for graduate school, so her next year would be spent tending the bar and figuring out where to go with her life. She was in her 20s, wasn't this what she was supposed to do?

The evening became a rush as people poured into the bar from the streets, and soon Caroline had people lining up to congratulate a complete stranger, basking in all of the attention coming her way. She happily flashed her ring to anyone and everyone who asked to see it, and proceeded to squeal at the top of her lungs and go over every minute detail about the proposal when their other best friend Bonnie arrived.

"I told you she'd say yes!" She shouted to Stefan over the pulsating music wafting from the speakers. She smiled at him and slid his favorite beer across the bar. "Congratulations."

"Thank you," he told her before Caroline stole his attention away, sliding her body between his and the bar.

"Hi baby," she smiled at him, wrapping her arms around his neck and littering his face with kisses.

Elena watched the happy couple with a smile. They'd met in Caroline's English Literature class her junior year at NYU, and the moment Stefan stood up and introduced himself as the TA for the class, Caroline swears she knew that he was going to be hers.

Stefan had tried to fight her at first, but Caroline was persistent, and the pull was just too much in the end. Just over a year and a half later, and now they were engaged. Caroline had her life all figured out, and as always, it was going perfectly according to plan.

Stefan and Caroline soon disappeared into the crowd, probably off whispering sweet nothings into each other's ears. She was left, busy at her job, until her other best friend showed up. "So, where's Matt?" Bonnie asked when she sidled up to the bar sometime after 11.

Without needing to be asked, she began to mix a drink for Bonnie. "I don't know," she finally said when she presented the finished product to her friend. "We're kind of fighting."

"About what?"

"Same thing as always," she sighed and rolled her eyes.

She'd been with Matt on and off since her freshman year and his sophomore year at Columbia, when they met at a fraternity party at the beginning of the semester. He'd since graduated and had gone on to law school, while her life moved along at a snail's pace. Since he graduated, he'd been asking her to move in, but she always refused, telling him that she didn't want to make a commitment that big until she had her life more figured out.

The more he pushed to try and get her to move in, the harder she pushed back and withdrew from the relationship, but even when they broke up, they still got back together. Some days she wondered if it was worth it, but she'd been with him so long and he was one of her best friends. He'd been by her side through everything since she was 18, never letting her down. He was her first love and she knew that one day they'd get married, she just didn't want to make that commitment right now, and she was scared that if she moved in with him, soon they'd be engaged, and next thing she'd know, they'd be in the suburbs with three kids.

Bonnie reached over the bar and squeezed her hand. "He'll come around when he cools off. He always does."

"I know," she nodded her head, because it was true. He'd take a few days, maybe a week, calm down, and then act like nothing had happened. "We'll be fine."

"Oh God," Caroline groaned, throwing herself against the bar after untangling herself from Stefan long enough to come up for air. "I know that look," she waved a wobbly finger in front of Elena's face. "You and Matt had a fight because he wants to move in together and you don't want to. Let me save you the trouble of it all. He'll stay mad for a couple days, and then you'll have hot makeup sex only to have the fight all over again in a couple months. So," she slammed her hands down on the bar. "Stop focusing on him and focus on me. I'm engaged!"

Knowing better than to argue with Caroline, she just smiled and prepared another drink for the bride-to-be.

"I'm gonna kill her before she even makes it down the aisle, aren't I?" Bonnie questioned after Caroline launched herself back at Stefan, where he was talking to a guy she'd never seen before. He had hair as black as night, and eyes as blue as the ocean. They were such polar opposites; his eyes shined all the way from more than 10 feet away. "Elena!"

Bonnie snapped a finger in her face, bringing her attention back to her friend.

"Yeah," she shook her head. "Sorry, what were you saying?"

"I was saying that I was probably going to have to kill Caroline before she even made it down the aisle."

"Depends on who she makes her maid of honor. If it's me, I'll probably beat you to the punch." She saw someone motioning to her from a few feet down the bar and excused herself from Bonnie, putting herself back to work for nearly another 30 minutes before she could make her way back down to Bonnie, who returned to the bar when she saw that Elena had a moment. "Who's the guy with Stefan?" She motioned her head to the man she'd seen chatting with Stefan earlier.

"Oh him?" Bonnie grimaced when she looked at where Elena was motioning. "Apparently that's Stefan's brother, Damon."

"You don't like him?"

"Kind of an asshole." She shrugged her shoulders. "Keeps telling Stefan he shouldn't get married. I'm waiting for Caroline to use her ring to gauge one of his eyes out."

"That would be interesting to watch." At that exact moment, Caroline stomped her foot on the ground and narrowed her eyes at Damon. She shoved a finger in his chest and then turned on her heel, leaving him smirking behind her, while Stefan slapped him across the back of the head. "What happened?"

She took note of the empty glass in Caroline's hand and began mixing a fresh drink for her. "Just because he has serious parental issues and one raging bitch of an ex, doesn't mean he needs to take it out on the rest of us." Caroline huffed out before gratefully taking the new drink from Elena's extended hand. "Thank you."

"Well, at least he's hot." She tried to offer, because honestly, the man was gorgeous. Those eyes and that hair, combined with the pale skin, and lean body, would make any girl do a double take.

"Oh, he knows it." She glanced over her shoulder, shooting daggers in his direction. "Asshole."

"Okay, you keep trying to light him on fire with your eyes and I'm going to go try and make some more money."

"Have fun," Caroline shouted at her before turning to glare at Stefan's brother again.

At midnight, the bar got one final surge that kept her busy for an hour, her hands moving so quickly she barely knew what she was making half of the time. She graciously turned down dozens of shots, a few marriage proposals, and pocketed enough phone numbers to make a phone book, even some from clearly taken men. The girlfriends glared at her, but most were never paying for the drinks, so it never affected her tips, just possibly her karma somewhere down the line.

"I'll have a Bud Light." Her head shot up at the sound of Matt's voice. He was standing in front of her, hands shoved loosely in his pocket, a lazy smile on his face. "And a water for the taken bartender."

"Hey," she sighed out, and even though he couldn't hear her because of the music, he understood. "I didn't expect to see you tonight."

"Yeah, well, I could only sit in the library for so long without going crazy, and Caroline called and told me if I didn't come celebrate her engagement she would come castrate me."

"I'll cut her off." They shared a laugh as he glanced back at Caroline, who was in fine spirits now, smiling widely at whatever Stefan was whispering in her ear.

He took the beer from her and set it down on the bar, reaching back for her hand and holding it within his grasp. "I'm sorry about the fight."

She shrugged and gave him a small smile. "Me too."

"We good?"

"Yeah," she nodded her head. "We're good."

"Okay, I'll let you get back to work while I go congratulate Caroline before she gets her hands on a knife."

"Tell her I said she's cut off." She watched as he went over and gave Caroline a hug before shaking hands with Stefan and congratulating both of them.

She felt a wave of comfort wash over her now that their fight was over and things would return back to normal. He was the one constant in her life and she hated when they fought. It left her uneasy and feeling horrible.

The bar began to clear out soon after Matt came in, and they all began to make their way toward the bar now that it wasn't so crowded.

"Alright, shots of tequila for everyone, even you, Elena." Caroline announced, holding her arms high above her head. She began to object but Caroline cut her off before she could begin. "The bar closes in less than an hour, that means you can do a shot, because I'm your best friend and I just got engaged, and I told you so."

Knowing better than to argue, Elena pulled out enough shot glasses for everyone and filled them with tequila. She passed them around to everyone, and they all held them in the air, waiting for someone to make a toast.

Finally, Stefan cleared his throat and spoke up so they could all hear him. "One year ago, Caroline threw herself at me in the back of a lecture hall at NYU, and I thought that I was going to have to spend half the semester dodging her, but she wouldn't give up, and I finally gave in." He glanced down at his new fiancée who was beaming up at him. "I'm so happy that I gave in, because I cannot imagine marrying anyone else. I love you."

"To Stefan and Caroline!" Elena proclaimed, and they all joined their glasses together and cheered before swallowing the shot. She shivered a bit as it ran down her throat and shook the burn off.

"Yeah, well tell her I said to kiss my ass." Her head turned to the sound of an angry voice, and she saw Damon coming toward them, his phone pressed to his ear. "She's not getting dick, and you can quote me on that. She's. Not. Getting. Dick!"

"Katherine?" Stefan questioned his brother after he'd ended the conversation and joined the group.

"Who else?" he flashed an angry smile, and she could see the muscles in his jaw twitching furiously. He leaned up against the bar, hanging his head in her direction. "Scotch on the rocks, make it a double, and the best you have in this place." She stood, frozen for a few moments, unable to move. Then he snapped at her. "That is your job, right? I haven't been imagining that all night?"

"Right, sorry!" She snapped to attention and turned to the shelves behind her, reaching up for the best bottle of scotch in the bar, having to stand on the tip of her toes to reach it. She made quick work of fixing his drink and sliding it over the bar to him. "There you go."

"Thanks." He pulled a $100 bill out of his wallet and handed it over to her.

She stared down at it, eyes wide, before looking back at him. "Um, do you want change?"

"Keep it." His eyes raked over her, making her tremble nervously. "You obviously need it more than I do."

"Excuse me?" she questioned, a hint of disbelief in her voice.

"Elena, meet Damon, Stefan's brother and anything but a best man!" Caroline explained, faux smile plastered to her face as she motioned between the two of them. "Damon, meet Elena, my maid of honor."

She turned to Caroline and brushed off Damon's words. "What, I'm your maid of honor?"

"Yup, congratulations!" She waved her hands in the air before dropping them to her side and glaring at Damon. "Have fun planning mine and Stefan's joint bachelor and bachelorette party."

Damon smirked at her and held out his hand for her. "Stefan, your wedding officially just got more interesting."

Caroline reached out and slapped Damon's hand away before Elena could shake it. "She's taken; back off, and stop doing that eye thing."

"Just because there's a goalie doesn't mean you can't score."

Matt immediately choked on the mouthful of beer he had been trying to swallow and Elena reached across the bar to hit her hand on his back. "You okay?" She couldn't believe this man that she didn't know had just said that. She thought things like that happened in movies, not real life. Who said those things?

"Oh, so you must be the boyfriend." Damon deduced the dynamic after a quick glance between Elena and Matt. He almost looked apologetic for a second, but then he shrugged his shoulders. "Oh well, you'll hate me soon enough anyway."