Chapter One: Uncharted

"I'm already out of fool-proof ideas, so don't ask me how to get started."

Elena sighed as she stood in line waiting to order her coffee. She had her phone pressed to her ear with her shoulder, and was struggling to pull her wallet out of her purse. Her sister was talking a mile a minute, making it insanely difficult to concentrate. This was what she got for answering her sister's phone call in public, she supposed. What was she supposed to do? Her phone had kept vibrating all through her run, she'd just assumed it was an emergency.

About halfway between 'Elijah' and 'woke up this morning,' Elena had stopped listening. She really wasn't in the mood to talk about her sister's committed boyfriend of five years. Not after she had broken up with her not-so-committed boyfriend of two weeks the night before. It wasn't that she was upset – the guy had turned out to be an ass – she was just angry with herself. She was twenty-seven. She should have it all figured out by now – marriage, children, a career. Instead, she worked in a bar every night and went out with seemingly good guys who just wanted to get into her pants.

Here was her baby sister, seriously dating this great guy at twenty-three. She had it all. She'd gotten a great job right out of college, she made two more figures than Elena, and she was probably going to be the first to have kids. Katherine's life was just perfect, and Elena's was perfectly. . .unfulfilling. Moving to New York with Caroline hadn't done anything but had her watch her best friend get married and deal with said best friend's new brother-in-law incessantly. She was miserable.

Before she could finagle her wallet out of her mess of a purse, she was up to order her coffee. She looked up distractedly at the waiting barista and ordered the first thing that came to her mind. "Regular coffee, medium," she requested as she finally got her wallet out into the open. The barista nodded and took the card Elena held out.

"Are you getting coffee?" Katherine asked, pulling Elena back into their conversation.

"Yeah, I had a rough night," Elena said as she took her card and receipt back from the barista and shoved them in a nondiscriminatory manner back into her purse. She stepped out of line to go wait in the pickup line. She swore if she had to wait in one more line today, she'd throw something out the window.

"What happened?" Katherine asked, trying to be considerate even though Elena knew she really didn't care. This entire time she'd been building up to something, and now Elena's drama was just a roadblock to that.

"It doesn't matter," Elena said quickly. "I know you want to tell me something. Spill."

At the same time the barista called out, "Medium regular coffee." Katherine said, "I'm getting married!"

Elena reached out distractedly to grab her coffee and almost dropped it in the process. Her mouth hung open in shock, and she stood at the front of the line, completely frozen, until the person behind her snapped at her to move. She almost yelled at the rude New Yorker, but decided against it. She just took her coffee and rushed to sit down at one of the empty tables.

"Say something!" Katherine said excitedly.

Elena swallowed the urge to hang up. She was happy for her sister, of course she was. This was just too much though. Right here, right now, her mind wasn't in a good place for her to talk about her baby sister getting married long before her. It was that moment she realized what a mess her life had become. The moment you realize your sister has far surpassed you in every way, shape, and form, is the moment you get the hell off the phone before you break down.

"I'm so happy for you," Elena said, trying as hard as she could not to convey how she was really feeling. "Really, Katherine. I am. We can talk more later, okay? I have to go do a couple things."

"Okay, I'll talk to you later! Love you!" Katherine said, making a dramatic smooching sound before disconnecting.

Elena slowly lowered the phone from her ear and placed it on the table. She focused on breathing – in and out, in and out – while staring at her cup of coffee. She jumped when a hand suddenly closed around it and lifted it from the table.

"Excuse-" she started, looking up to see who'd had the audacity to steal her drink from right in front of her face. Her eyes narrowed when she saw who it was. Of course. "What the hell, Damon?" she snapped. He sat down and made a face as he drank the coffee from her cup.

"Since when have you liked it black?" he asked, taking another sip.

Elena was fairly certain she'd never shared her preferences in coffee with him, but she decided to let that detail go. "Never." Her voice was begrudging, her eyes hard on his. She was definitely not in the mood for his antics today – or any day, but especially today.

"Then why order it?" he continued grilling her, while drinking what she had paid for.

"I was distracted," she told him, more annoyance seeping into her tone. She was hoping he'd get that she didn't want him here, but no such luck occurred. He just continued sitting and drinking her coffee, unbelievably oblivious to her sour mood. Elena suddenly had the overwhelming urge to smack him upside the head.

Just as she was about to reach across the table, her phone began to vibrate. She looked down at the caller ID and saw that it was it was her Great Aunt Kathleen calling. Groaning out loud, she took the phone in her hand and prepared to hear all about not being married yet, and then being asked if she was in a serious relationship yet, and then being told why she wasn't.

"You have to answer," Damon said matter-of-factly as he watched her battle with herself over whether or not it was worth it. "She could die soon," he told her, pointing at the 'Great Aunt' title on the contact information.

"You're an ass," Elena said, but answered it anyway. She quickly adjusted her tone and held the phone to her ear. "Hello?"

Her great aunt's voice came through small, but strong nonetheless. The woman was nearly ninety years old and was just as strong as she was twenty years ago. It was amazing. "Elena, darling," she said. "I heard the great news! You're getting married, how exciting!"

Elena had the serious urge to smack her head on the table. Damon caught onto her expression and hid his smile by taking another sip of coffee.

Gritting her teeth together, Elena prepared to tell her very traditional great aunt that she still wasn't getting married, her sister was. "Aunt Kathleen, I'm not getting married. That's Katherine."

There was silence on the other end for a moment and Elena braced herself. "I should call her then. Don't think we're done here, dear. We need to have a good, long talk about your choices."

With that, her aunt hung up, leaving Elena to thank God it didn't turn out to be a long monologue on what she was doing wrong with her life. Granted, that talk would probably come at some other inopportune time, but she was just glad it wasn't now.

"Thank wasn't too bad," Damon acknowledged with a smirk. "So, your sister's getting married? That must suck."

Elena took a deep breath and blew it out through her mouth. "It doesn't suck," she told him. "What sucks is that I'm twenty-seven and can't hold onto a guy for more than fourteen days, while she's going to be off planning her wedding for the next ten months."

Damon shrugged. "I'm not doing much better."

Elena narrowed her eyes. "That's because you choose not to do better. You like the incessant flow of girls through your bed every night. You can't tell me you don't." Her eyes challenged his and she grabbed her coffee from him and took a sip. It tasted bitter and disgusting, but she kept her face straight. Proving a point wouldn't work if she faltered.

"Of course I like it, Elena," he scoffed. "But that doesn't mean I wouldn't ever settle down."

Elena shook her head and leaned back in her chair. "I just don't know what I'm going to do," she muttered. "I'm going to show up at my sister's wedding with not so much as a boyfriend and I will never hear the end of it. God, I just want to die in a hole right now."

Damon raised his eyebrows at her. "You're being a little melodramatic, Elena."

He was right. She was making this all about her, when in reality it should have been all about Katherine. Weddings weren't about the single sisters, they were about the happy brides. She just had to keep reminding herself of that. It wasn't about her getting compared to her sister for the thousandth time, it was about her little sister finding someone that made her happy. That was all. It was just remembering that amongst her own drama that was going to be hard.

"I'm such a bitch," she groaned and leaned forward, resting her forehead on her arms.

"No," Damon consoled her. "Only to me, but that doesn't count. I felt the same way when Stefan got married before me. Although, to a much lesser extent. It was a little embarrassing is all."

"Why are you being nice to me?" Elena asked him. She'd been nothing but rude to him since the day they'd met. In all fairness, he usually wasn't any nicer to her, but still. She didn't deserve his kindness, especially with all the selfishness swirling through her head right now. She didn't deserve anyone's kindness.

Damon shrugged. "I know we don't like each other, but I figured being mean to you right now would just be rude."

"That's never stopped you before," Elena challenged, placing her chin on her arms and looking up at him.

"Maybe I don't feel like fighting with you today," he leveled. "Can we move on?"

Elena sat up and crossed her arms over her chest. There was always something about Damon that rubbed her the wrong way. Whether it was his arrogance, or sense of humor, or ability to basically read her mind when it came to feelings, it just all bugged her. For two years she'd known the man, and in all that time she'd never once considered him kind. That was exactly what he was being right now, though. He wasn't antagonizing her, or telling her what she felt, or making some gross sexual joke. He was just talking to her and being a decent human being. She never thought she'd see the day.

Damon looked at her curiously for a moment, trying to pinpoint exactly what she was thinking. "I can do it, you know," he said with a smirk.

"You can do what, Damon?"

"I can pretend to be your boyfriend when your sister gets married."

Elena stared at him incredulously. "You have got to be kidding me," she said before she could stop herself. "Damon Salvatore doesn't do favors for anybody."

His eyes narrowed. "He does them for Elena Gilbert," he said seriously. "Listen, I don't want to have to hear you whine about this for the next however many months until her wedding. I'll pretend to be your date, we'll go to this thing and then we can go back to hating each other. Problem solved."

"No," Elena said, standing. "Did you miss the part where we don't like each other? We'd never pull it off. I'll find an actual boyfriend, thank you."

She brushed past him and exited the coffee shop. She ignored her phone as it rang, knowing it was him, and began down the street toward Caroline's apartment. Her fingers were tight on her phone as it vibrated again. She didn't bother to look down before she picked up.

"Look – Damon," she started. She was going to attempt to explain to him that it was an awful idea. A fake relationship between them would be as bad as a real one, and she just couldn't handle that right now. She wasn't mad about the idea, but she was put off that he thought she needed a fake date before she even tried to find a real one.

"Um, it's Katherine," Katherine's voice came through. "But I am interested to find out who Damon is. Do you have a boyfriend you haven't told me about, Elena?"

Elena groaned and kept walking. Of course she would make a mistake like that. She was always getting herself into these kinds of situations – the ones where people thought she was doing something that she wasn't, proceeded to get excited, and then completely disappointed in her when they found out they'd been wrong. It was getting ridiculous.

"Damon is Caroline's brother-in-law," Elena said, jogging through the line of stalled taxis on Broadway. One honked at her for no apparent reason, but she just brushed it off. Sometimes, honking was seen as flirting. Gross, sweaty, taxi driver flirting.

"Well, that doesn't mean there's nothing going on there! Your turn to spill."

Elena stepped up onto the curb and looked around for any excuse to get off the phone. She'd already made a lame excuse not an hour ago, and now she wanted to make another one? Her sister skills needed work. "Nothing's going on, Kat," Elena assured her, picking up her pace so she could get to Caroline's and off the phone faster. "He's an ass."

"Is he hot?"

Elena rolled her eyes. Of course, that would be the first question on her mind after hearing he was an asshole. It didn't matter to Katherine what a guy was like, as long as he was attractive. She was surprised she was marrying a nice guy – the first nice guy she'd ever dated.

"Yeah," Elena said honestly. Because Damon was hot. She'd be lying if she said she'd never thought about sleeping with him in the two years they'd known each other. She may not have liked him as a person, but she sure as hell was attracted to him.

"Sleep with him then! Girl, you need to get laid. I can sense it from here."

"It's not that simple, Katherine," Elena told her. "Anyway, what's up?"

"Well, since you so rudely hung up, I'm calling to tell you that you'll be my maid of honor. And that means that you'll have to handle the wedding alone for a while until I can get the time off to come up there and help you get every situated."

Elena blinked. She knew she'd be maid of honor, but she didn't know she'd be doing all the planning alone. "Have you set the date?"

"June twenty-first at this gorgeous resort on Maui," Katherine said gleefully.

Elena's eyes widened and she stopped suddenly, resulting in the person behind her to nearly run into her. "Katherine, that's four months away," she enunciated. "Are you crazy? I can't do all the planning for a you wedding by then alone! Especially if it's going to be in Hawaii."

"I believe in you," Katherine said. "I'll send you my color scheme and vision. You have perfect taste, and if I don't like something we'll fix it. Everything will be fine."

Katherine hung up, leaving Elena to stare at her phone in dismay. She'd planned Caroline's wedding, but she'd had Caroline looking over her shoulder constantly. Planning a wedding completely by herself for however long until Katherine could get up to New York sounded like nothing short of hell.

With a sigh, Elena quickly hurried for Caroline's.

"Katherine's getting married," Elena said, after going to Caroline's kitchen and retrieving a bottle of water from the refrigerator. "She wants me to do all the planning until she can get up here to help."

"Well, that ought to be fun," Caroline said, leaning against her counter. "She's not as big of a control freak as me. "

Elena took a sip of water and nodded slowly. "You're right. It's just. . . it's so soon. The date is in four months. I don't have time for this."

Caroline smiled. "You don't have time to plan this wedding, or you don't have time to find a stable boyfriend to bring home to your family who all expect you to have one?"

Elena groaned. "Both? I don't know Caroline. Is it even worth it? I mean, whatever I do I'm going to do it wrong. It doesn't really matter if they think I'm seeing someone or not. If I was, they'd probably hate him anyway."

"What do you mean if they think you're seeing someone. If you bring a guy to her wedding, you will be seeing him. Right?" Caroline looked at her suspiciously, catching onto her strange wording. Elena gritted her teeth together. She just needed to keep her mouth shut. This was her best friend, though and she hoped she wouldn't judge her too badly for even entertaining the thought.

"Damon offered to pretend to be my boyfriend. Just so no one would be nagging me the entire time," Elena admitted, shrinking a little bit. If Elena didn't like Damon, Caroline hated him. The only person who wasn't aware of her loathing was Stefan, who was able to stay blissfully unaware of Caroline and Damon's more than unfriendly relationship. Everyone else, however, knew to avoid Damon in any conversation with her.

"Elena," she hissed. "You aren't considering it are you?"

"No, of course not! But if I can't find anyone by then, I might have to start."

Caroline shook her head. "Don't worry, Elena. We are going to find you someone, and that someone is not going to be my rotten brother-in-law. I will not allow that to happen."

Elena took a deep breath. If anyone could play matchmaker, it was Caroline. "I'll only let you play matchmaker if you help plan this wedding."

Caroline smiled. "Deal."

A/N: There you have it, chapter one. If you made it to the author's note, I am proud! I think it's a little all over the place, but things will definitely be cleared up and elaborated on in future chapters. If you have anything you specifically want to know, go ahead and drop it in the reviews (along with what you thought of the entire thing, of course) Reviews are my life source! Anyway, I hope you guys liked it!