Author's Note: Everything other than Damon's thoughts are based off my personal life (other than the boyfriend part). So this story isn't going to have any more chapters or anything its just a one shot to help vent my feelings about unrequited love. Sigh.

Damon and Stefan aren't brothers. AU

Elana was surprised when Stefan, her boyfriend, showed up at her work. She and her boss Damon had been in his office discussing last minute work that needed to be done before the weekend when Caroline, the secretary, interrupted them to announce that Elana's boyfriend was there to whisk her away for a surprise romantic night on the town. Elana found herself trying to casually glance at Damon to gauge his reaction to Caroline's news. Elana had always had a small crush on him (the man was extremely attractive) since she started working at Salvatore Incorporate, but the age difference of seven years was something she always felt got between them. It also didn't help that she felt they had little to talk about other than their work and their occasional drinking escapades. Nonetheless, Elena still felt a pang of disappointment when she saw that Damon's expression was painfully neutral. She sighed. Well duh, he didn't feel anything for her. He was seven years her senior was a workaholic/alcoholic who still lived with his parents. On top of that Damon was her superior. Their interests and lives were totally different. Too different if Elana was being totally honest with herself. She just liked to trick herself into thinking that maybe something would happen between them but that was naive. After all, this job was only a stepping stone for a future that would take her far away from Mystic Falls. The reality was that in a few short months she probably would never see him again. Returning to the present she smiled at Caroline and said she'd be out in a minute. A moment of awkward silence fell between the pair, but Damon quickly broke it.

"Well, have a good weekend Elana, thanks for your work today. Don't worry about locking up. I'm going to finish up some paperwork and I will see you next week."

Elana flashed him a smiled, offered up her thanks, and quickly left Damon's office to greet her eagerly awaiting boyfriend. The minute Stefan laid eyes on her he swept her up into a large embrace and gave her a sweet kiss on the lips. She laughed lightly when they parted, grabbed her purse and coat, and left the office holding onto Stefan's hand tightly. But as she exited the building she allowed her mind wander back to Damon.

As Elena walked out the door of his office, Damon tired to focus on the spreadsheets that were laid out in front of him. But he couldn't help but look up from his work, and through the large window that overlooked the rest of the office, Damon was greeted with the sight of Elena's boyfriend holding her tightly and leaning down to give her a kiss. Ok he got it. Elana clearly had a life outside of work that included romance and sex. He didn't need her to shove it in his face. He grumbled slightly and turned back to the spreadsheets he was trying to complete before he went to the bar and drowned himself in alcohol. Damon didn't want to admit to himself how painful it was to know that the only time he got with Elena was when she was in the adjacent office working from nine to five. He wasn't a part of her life outside of the office and he wasn't entirely sure he'd fit into her happy world anyway. She was better off with someone her age, who fit in with her friends and her family. With that final unhappy thought he forced himself to become immersed in the spreadsheets, and when he looked up again the happy couple was gone.

Author's Note: Everything other than Damon's thoughts are based off my personal life (other than the boyfriend part). So this story isn't going to have any more chapters or anything its just a one shot to help vent my feelings about unrequited love. Sigh.

Damon and Stefan aren't brothers. AU