Preface

Firstly, I want to thank everybody who has read, reviewed, and supported my work. I wouldn't be writing now without all of you, and writing is helping me stay sane at the moment. I also want to thank all my fanfiction friends (you know who you are) for your support whenever I've been feeling low about my writing, or anything else for that matter.

Secondly, I want to state that this story is being written in absolute chaos. Between my six week old baby, and my almost two year old, things are pretty crazy. Sleep is a thing of the past at the moment, and mess seems to accumulate much faster than I can clean it up. My brain is mush, so I'm going to ask you to overlook any really awkward sentences, or errors.

Thirdly, I haven't abandoned 'Bet Me', but in my muddled up state, I need to work on something that requires a little less of my attention, and so I decided to write the kind of story that I love to read. One of my favorite story lines, ever, is about friendships between men and women, where one or both of the parties are in denial about how they feel. I've always wanted to write one, but haven't because there are plenty around.

I love DE, and their friendship, and I'm excited to see them develop this season, but I'm aware it's going to be painful at times waiting for Elena to deal with her feelings for Stefan. And so this is more of my TVD style therapy for me (like Tonight We Tell The Truth was), because watching Damon suffering wears me out. By writing this AU/AH, I can play with their friendship, turn it on it's head, and change the dynamics. I'm finding that writing one of my fave story lines is a lot less demanding. I'll return to Bet Me when I have more time.

There is a substantial amount of Stefan/Katherine in this. They're not my favorite couple by any means, so writing them has been an interesting experience for me. In my mind, Damon and Stefan are actually half brothers here, but neither one of them knows it. I doubt it will come up in the story either.

I think that's it. Apologies for the long note, and on with the story.


Chapter One

A Resolve Is Born

Despite the fact that Elena Gilbert loved her best friend Damon Salvatore to a fault, there were times when she wanted to shake some common sense into him. This was one of those times.

"I can't believe she left me for that ass-kisser. I mean, what does she see in him? Ugh, he's so boring."

It wasn't the first time Elena had heard Damon make these comments about his long-time work rival, Stefan. It was a sick and twisted game the two men played, spurred on by their employees, Klaus and Elijah Smith. A competition over who could win the affections of a selected target was something Elena thought totally despicable. Damon had lost the latest round of their game to Stefan. Usually Elena would tell him he deserved anything he got for partaking in such foolish games, but something was different this time. Most women walked in and out of Damon's life in the blink of an eye, but Katherine Pierce had walked in, and she'd never walked back out.

What Elena wanted to tell him was, 'you're better off without that heinous bitch. You need someone who loves and appreciates you, like I do.' Instead, however, she knocked back another shot of tequila. She'd never told him how she felt. Damon had broken so many hearts over the years that there was a group of Damon's ex-girlfriends who met weekly in town to bond over their pain, and throw darts at a cut-out of his face. Elena chose not to join that club. She had been friends with Damon for a long time, and the thought of losing the one constant in her life; the person who had been there for her through every success, every failure, every break-up, had stopped her from telling him how she felt.

"I have to get her back, Elena. I'd do anything."

"Women don't matter to you. That's what you tell me."

Elena knew Damon didn't count her in that, because fortunately, or unfortunately, depending on how one looked at it, Damon didn't see her that way. It had never worried her before, because he'd always made it his business to get out of any relationship, or fling, before he fell in love. For self-preservation, she'd never seriously contemplated letting him know how she felt. The bartender put more shots in front of them. Elena downed her two, and watched Damon drink his.

"Katherine's different," he told her.

"How?"

"I think I'm in love."

Elena felt as if she'd been sucker punched. Out of all the things she expected him to say, she'd never expected to hear him say that.

"You have to help me, Elena."

Elena couldn't believe it. She'd always thought that if he ever felt that way about a woman, it would be about her. She'd never contemplated Damon would go ahead and fall for that shrew of a woman. He couldn't be serious, could he?

"Tell me what to do," he pleaded.

His gaze was pleading as he looked at her, and the desperation in his voice disturbed her. There was nothing she wouldn't do for him, but when it came to winning women back, she didn't have much practical experience, not to mention the fact that he didn't belong with that woman. In was on the tip of her tongue to tell him so, but the look of anguish on his face kept her quiet. He really was serious. She was reeling. She needed a moment, but from the way he was looking at her, she didn't have one. She wracked her brain for something to tell him.

"I don't know, Damon, in the movies they use jealousy when they want to win someone back."

"Jealousy?"

"Yeah, you know, that horrible green emotion that makes you want something that someone else has," she said, trying for a joke. He didn't smile.

"I know what jealousy is, Elena. How do I make her jealous?"

"Pretend to be with someone else. Show her you've moved on, and don't want her anymore."

"Does that ever actually work?"

"I don't know. I've never tried it. It works in the movies though."

Damon looked at her thoughtfully. "Katherine never liked you."

"I know."

He made a face. "She thought you were in love with me."

Elena swallowed hard.

"It didn't matter how many times I told her you weren't," he continued. "She never believed me. She hated it whenever I spent time with you."

"She was insecure."

"She was jealous," Damon said to her.

He was looking at her now, his eyes brightening a little; a small smile playing around his lips. Suddenly Elena had a very clear idea of where this was going.

"Oh no," she told him.

"Yes," Damon said decisively. "It's perfect. She'll hate it if she thinks we're together."

"It's crazy," she told him desperately.

"It's genius."

"Someone else would be a better choice."

Anyone else would be a better choice than her. She couldn't do it. She couldn't 'pretend' to be in love with him. What if she faked it a little too well? What if he realized the truth, and then what if that ruined everything?

"It wouldn't work with anyone else," he told her. "She'd never believe it."

"Forget it. It was a stupid idea."

"Come on, Elena."

"No. I won't be a part of this stupid game you play with Stefan."

"I love her."

Elena could do nothing but look at him. He really believed it.

"You know I'd do it for you," he said to her.

He would. He would do it for her. He'd done crazy things for her, and he never asked for a thing in return. Until now. How could she refuse him? It had been her idea after all; her very stupid idea. If she said no, he would want to know why. What valid reason could she give him? None. She had nothing. Her eyes strayed to the empty shot glasses in front of her. They had had an awful lot to drink tonight. Maybe he'd forget this in the morning. Maybe, if she plied him with enough alcohol, he wouldn't remember any of this conversation.

She ordered more shots for them. "Okay," she said to him, hoping the alcohol would work a miracle. "I'll do it."


Hours later, Elena helped Damon up the stairs to his apartment as best she could. It wasn't easy, but they struggled up one step at a time, all the while Elena cursed the lifts for being out of order. She'd stopped drinking an hour and a half ago, while Damon had kept drinking right up until they left the bar. Now she was feeling no end of guilt for shamelessly trying to get her best friend drunk.

"Keys?" she asked him, when they'd finally reached their destination.

"Pocket," he mumbled.

Elena delicately reached into his jean pocket and fumbled around trying to get her hand on them. It was a testament to just how drunk he was that he didn't give her one of his flirty comments. Instead he just grunted. She finally fished them out, unlocked the door, and then they stumbled through it with his arm around her. When they reached his king size bed, Damon fell onto it, pulling Elena with him.

She landed on top of him with a thud. His eyelids, which had been drooping both from fatigue and the effects of alcohol, now fluttered open. She pushed against him, trying to get up, but his arm was still heavy around her, trapping her against him. His eyes locked with hers as she moved against him, making her breath catch. She was suddenly all too aware of how her feminine curves melded against his hard male body; of how close his lips were to hers.

"Damon."

He released her, and she rolled off him, and onto the other side of the bed.

"Stay," he mumbled. "You're tired."

Elena was about to say no, but lack of sleep, and all those shots were catching up with her. She didn't feel like having to make her way back downstairs and catch a cab back to her place, especially when she was already in a bed that was so comfortable. Still, she should go. She was just about to tell him she was leaving when she realized he was already asleep. She got out of the bed and pulled the covers up and over him.

He stirred slightly. "Katherine," he mumbled, eyes still closed.

That was her cue to leave, Elena thought; her heart squeezing inside her chest. With any luck Damon would forget that woman, and if he didn't forget her, hopefully he would at least forget Elena's stupid suggestion from earlier on this evening. Closing his front door behind her, Elena thought she would have to wait till tomorrow to find out if she was lucky or not.


Damon closed his eyes against the sun beaming through the window. Why did he feel so damn awful? That's right; he and Elena had spent the better part of last night doing tequila shots. This was Elena's fault, he decided. Sure he'd been the one to suggest they go the bar, but the tequila had been her idea. She'd gone shot for shot with him for a while there, but then she'd been sensible enough to stop. He hadn't. Now he had a blinding headache, and no desire to go to work.

Damon got up, headed straight for his bathroom cabinet and took out pain killers. He had to go to work today. If he didn't, Stefan would get the edge on the highly prized Brewis Beer campaign they'd both been vying for, and he didn't want to give that smug idiot anything more to gloat about. Introducing Katherine to Stefan at his work dinner a month ago had been a big mistake. He swallowed the tablets with a mouthful of water from the tap.

He had a never ending calendar of work functions. Smith and Smith Advertising was one of those annoying companies that liked all their employees to 'bond' on a regular basis. Elijah and Klaus Smith made it mandatory for all their employees to attend monthly dinners, and a yearly working vacation at the Smith brother's home on their private island, "Heaven's Isle". Damon would have left the company ages ago if they weren't the best in the business.

At least they were allowed to take partners on the week long working vacation. He'd already asked Katherine to go with him, but now she was going with Stefan. Damon's lips twisted into an expression of utter disgust. He and Stefan had been hired on the same day, and Klaus and Elijah had always encouraged them to compete over everything, including women. At first it had been fun and light-hearted, but now it was an all out war. Lexie had gone to Stefan. Isobel had gone to him, and the tiebreaker, Katherine, had gone to Damon first, then Stefan.

He never let women matter to him, but there was something about Katherine that had changed that. He still wanted her. He missed her. That had to be love didn't it? He'd never been in love before, but this must be what love felt like. It figured that the first woman he fell in love with would leave him, just like his mother had left his father years ago. His father had fallen apart instead of fighting, though, and Damon wouldn't make the same mistake. He would win Katherine back. Elena would help him with that.

Elena. She was the greatest friend a guy could ever ask for. She was always there for him. They had something special; something that meant more to him than anything else in his life ever had. She knew him better than anyone, and she cared about him anyway. She accepted him completely, called him on his bullshit, and he knew he was lucky to have her in his life. He smiled as he stepped under the hot spray of the shower, remembering their first meeting.

He'd been hassling Billy Grayson for his lunch money at school. After Damon's mother left, his father had fallen apart like some weak, pathetic fool, drinking all the time, and then sleeping with women who would feed him. He left Damon alone to fend for himself, not bothering to stock the fridge or leave money for groceries. The only time Damon ate was when he took food, or money, off the kids at school.

Elena had tried to stop him from doing that on the first day he'd met her. She'd seen him roughing up Billy, and promptly marched up to him and kicked him very hard in the shin. Consequently he'd dropped Billy and turned on her.

"You'll pay for that," he'd said to her, backing her up against the wall in the empty corridor.

"Pick on someone your own size," she'd told him defiantly.

"I'll do what I want."

"You're a bully."

"Who cares?"

"Didn't your mother ever teach you any manners?"

"My mother's dead," he told her.

That wasn't the whole truth, but she may as well have died when she'd left Damon with his father, without even a goodbye.

"My mother is dead too, but I don't go around hurting other people."

"I wasn't hurting him," Damon said to her. "Well, I wouldn't have hurt him if he'd given me his money."

"Why do you need money?"

"So I can buy cigarettes," he lied.

He hadn't been about to tell some girl that he hadn't eaten in close to twenty-four hours, even if she was pretty.

"Gross," she'd said to him.

He grabbed her bag. "Now I'll just have to take your money."

"I don't have any."

He'd gone through her bag, and come out empty handed except for a sandwich.

"Fine, I'll just take this."

He thrust the bag back in her hands. At least he wouldn't starve today.

"That's my lunch."

"Now it's mine."

"Get your own sandwich."

"I just did."

"I don't have anything else to eat," she'd told him.

"Do I look like I care?"

"Please," she'd pleaded, as he started walking away.

To this day he still didn't know why he'd turned around, but he had. He'd seen her lip quiver as she held back the tears. Before he'd thought better of it, he opened the packaging roughly, took out half of the sandwich, and gave it to her; the idea of her being as hungry as he was suddenly making him uncomfortable. For whatever reason, the girl got to him.

"Thank you," she said, eating her half before he changed his mind and took it back. "I hate being hungry. My stomach rumbles. It's embarrassing. My foster parents don't give me much to eat."

"Well, I don't get anything to eat," Damon had told her angrily.

He couldn't believe he'd just told her that. He'd never told anybody that

"That must be awful."

It was awful, but he got by, when he didn't have some girl sticking her nose in his business. Her look of concern was almost too much. He didn't want to spend another minute with her.

"My foster parents are awful," she'd told him. "When they find my aunt, I can finally leave here."

Damon didn't care. He really didn't care to hear her ramble on about her life, her aunt, or her own hunger.

"Maybe you can show me round. This is my first day here, and I don't know where my next class is," she'd said tentatively, her cheeks turning a light shade of pink.

Damon stared at her. Had she not just seen him dangling Billy by the foot? As if he, Big Bad Salvatore as he was known around school, was going to play tour guide to some girl because he gave her half her sandwich back.

"Maybe," he said to her, "you can get lost."

He walked away, kicking a trashcan on the way out. He wasn't going to let some stupid girl ruin his reputation; first interfering in his business, then suggesting he actually help her. He didn't help anyone but himself.

In the coming weeks, however, Damon found out that that wasn't quite true. When Damon saw Tyler Lockwood trying to sneak his dope into Elena's bag before a bag check, Damon had kicked Tyler's ass, telling himself it was for the hell of it. When Amber Jacobs spread a rumor about Elena cheating on her test, because she'd taken Amber's spot at top of the class, Damon had put a tarantula in Amber locker, and told himself it was for his own amusement. And when he'd found Matt Donovan trying to feel Elena up after school one day, despite her evident dismay, he'd given the guy a bloody nose simply because it had felt good to. Damon had been suspended for that.

After he came back from suspension, Elena had sought him out to tell him that the Department of Human Services had finally tracked down her aunt, and that her aunt had moved to Mystic Falls over the weekend. He had been about to tell her he didn't care, when Elena had put her brown paper bag in his hands.

"What's this?" he'd asked her.

"Aunt Jenna gave me money and a packed lunch today," she told him.

"I don't want your stupid…"

She'd walked away before he could finish the sentence. Over the months that followed that exchange, Elena continued to give him her lunches. At some point he stopped denying he wanted them, and she had stopped walking away. The next thing he knew he was going round to Aunt Jenna's every night for dinner, and he and Elena were inseparable.

He still missed Jenna. Elena's aunt had passed away the year after Elena had graduated from high school. First Elena had lost her mother, then her father, and then she'd been thrown into three or more different foster homes before she'd moved in with aunt. When she'd lost Jenna too, she'd almost fallen apart. Losing anyone else would push her over the edge. Consequently she never had serious boyfriends, preferring instead to keep everyone at a distance. Well, everybody except for him.

What they had was solid. Dependable. They were always there for each other. They could always rely on each other, and he trusted her implicitly. If she thought making Katherine jealous would help him get her back, then he was willing to try. The easiest way to do that would be to take Elena on his work holiday in a couple of week's time. Klaus and Elijah were expecting him to bring someone anyway. He'd go see Elena on his lunch break. He couldn't wait to see her reaction when he told her what he had in mind.


Elena was eating her lunch when Damon turned up.

"What are you doing here?" she asked him, giving him a kiss on the cheek.

"I was in the neighborhood. Thought I'd drop by."

"Damon, you're never just in the neighborhood."

"Bonnie said you guys have been quiet lately."

"Things aren't too bad, though Anna hasn't had too many shifts since we hired her."

Elena and her friend Bonnie Bennett owned a second-hand bookstore in the center of Mystic Falls. They had just hired another person because they expected a rush on second-hand textbooks when school went back, but it hadn't started just yet.

"Well her luck is about to change."

"Why?" Elena asked him warily.

"I want you to come to Heaven's Isle with me in a couple of weeks."

"To your yearly work thingy?"

"Five days, six nights on the Smith's Island. Sun, white sand beaches, sunsets-"

"And work dinners, bonding exercises, and Klaus and Elijah Smith."

"So you take the good with the bad," he shrugged.

The Smith Brothers were over the top, and far too passionate about advertising in Elena's opinion. She also disapproved of the way they'd set Damon and Stefan against each other while preaching about work-place cohesiveness. Over the years she'd attended quite a few of Damon's work events with him, but he'd never asked to go on holiday with him. It was normally partners only.

"It's the perfect place to make Katherine jealous."

Elena's heart sank. He'd remembered. She should have realized the second he asked her to go. For a moment she'd though he wanted her to go with him for the pleasure of her company, but instead he wanted to use her to make Katherine jealous. She couldn't even be angry with him since he was just taking her advice. When she'd agreed to help last night, however, she'd imagined them going on a pretend date once or twice, not spending a whole week trying to make his ex-girlfriend jealous.

"I can't just leave for a week. I have responsibilities here at the store."

At that moment, Bonnie joined Damon and Elena in the small kitchenette at the back of the store.

"Anna can take over your shifts for that week," Bonnie told her. "If you want to go on holiday now is the perfect time. You know things will pick up when everyone goes back to school."

"You discussed this with Bonnie?" Elena asked him, starting to feel trapped.

"Damon mentioned it on the way in," Bonnie said, throwing an empty yogurt container in the bin and running her teaspoon under hot water.

Seeing as the two of them had already figured it out, she had no excuse. Damon was frowning at her now, as if not understanding why she wasn't over the moon about the idea.

"You don't want to come?" he asked her.

"You should go, Elena," Bonnie told her. "Anna and I can hold down the fort."

Bonnie was looking at her meaningfully. She probably thought she was doing Elena a favor, since she knew how Elena felt about Damon. Little did Bonnie know, however, that his taking her on holiday was all for someone else's benefit. Both Damon and Bonnie looked at her expectantly, waiting for her answer. It looked like she had no way out of this.

"Elena?" Damon queried, seeing her completely quiet.

"I can't wait," she told him, forcing a smile.

He looked wholly relieved as he slung an arm around her shoulders, pulling her close, making her feel and appreciate everything she was destined never to have.

"You and me in Heaven, Lena. What could be better?"

Bonnie rolled her eyes. "Very corny."

When Bonnie walked out, Damon started talking about how great their holiday was going to be. She had to stop doing this, Elena thought; she had to stop torturing herself. He just didn't feel that way about her. She'd waited. She'd waited years for him to realize he didn't want to keep all women at a distance; that he didn't want to walk out the moment he felt something for a woman he was seeing. Now that he had finally realized that, however, he still didn't want her. He wanted Katherine. It was Katherine who had turned his whole world upside down. It was Katherine who he'd let himself fall in love with.

Elena wanted Damon in her life; needed him in her life, but the truth was finally sinking in. No matter how she had hoped otherwise, she and Damon would never be more than friends. She had to stop pining after him like some love sick puppy. He was never going to look at her the way she wanted him to, and if she wanted to keep their friendship, it was time to move on. It was time to get over her best friend for good.


A/N: I hope you liked it. Thanks for reading, and please review.