Summary: At age 25 Elena is happily engaged to the man of her dreams. Until his brother she hasn't seen in ten years makes an appearance. Then her world comes crashing down when she realizes that everything she knew isn't what it seems. Damon may be her only hope.

Disclaimer: I own nothing! Everything belongs to their rightful owners.

A/N: This is actually a really old fic of mine based on 'Buffy' that was an unfinished fic. Every time I read it over and over again it just clicked that this would be a perfect story for Damon and Elena so I hope you all enjoy! I obviously changed a lot around, but please review and let me know what you think! Also big thank you to Aurora rose1001 (Mia) For beta-ing this for me! You rock!

Chapter 1 – Engagement

Elena Gilbert walked out her mother's gallery, the Gilbert's Fine Arts and Artifacts, and skipped happily to her car. She knew tonight was the night. The previous evening, her boyfriend, Stefan, had told her he wanted to take her to one of LA's finest restaurants and for her to dress in style. Elena navigated the well-known streets to her house, her thoughts careening around in her head. After she parked in front of her house, she ran inside as fast as she could and began getting ready.

Thirty minutes later, Elena stood in front of her mirror and carefully applied her lipstick. She puckered her cherry colored lips and smiled happily to herself. She just knew Stefan was going to love what she was wearing. She had gone on a shopping spree the day before with her best friend Caroline and found a gorgeous black silk dress that dropped to her knees and showed off her shapely legs. With its plunging neckline that showed off the curve of her breasts she knew she had to buy it.

A few minutes later the doorbell rang. Elena quickly looked herself over one more time then rushed down the stairs.

When she opened the door a pair of brown doe eyes met hazel. Elena gasped when she saw her boyfriend dressed sharply in black slacks and a gray silk shirt. He looked absolutely gorgeous. His brown locks were slicked back and he had an impish grin on his face.

Stefan smiled widely, gazing at Elena up and down before pulling her in for a quick peck on the lips.

"C'mon beautiful lets go, or we're going to be late."

After the dinner – which was wonderful – they decided to go for a stroll on the beach. They walked for a few minutes before they came upon a secluded section of the beach and Elena gasped when she saw the sight before her. Displayed in front of her was a red checkered blanket sprawled across the sand with champagne flute glasses and a bottle of champagne in a little cooler. Next to that was a small basket of food and a radio playing romantic melodies.

Elena looked up at Stefan with a goofy smile on her face. "You planned this," she whispered, still in shock.

Stefan just smiled and pulled her down onto the blanket. Elena settled herself in front of him and he wrapped his arms around her protectively. She kissed him underneath his jawline and inhaled his scent. She was going to make sure that whatever happens, this night stays imbedded in her memories.

"Elena I want to ask you something."

Elena's heart skipped a beat and began pounding in her chest. She looked up at Stefan and nodded softly.

"I know things haven't been easy for you lately with your parent's death and all…"

Elena got a glazed look in her eyes at the mention of her parent's. They had died over a year ago from a terrible car accident that claimed their lives.

"…but we have been together longer than I can remember." Stefan turned Elena around so that he was looking deeply into her eyes. His love for her so evident in the way he was gazing at her, "I love you more than anything in this world…" He stumbled a bit on his words obviously nervous with what he was trying to tell her. Elena nodded in encouragement and he continued. "Elena, what I am trying to say is, will you marry me?"

Elena felt tears well up in her eyes and she happily gathered the nervous man before her in a tight embrace then pulled away to kiss him passionately.

"I guess that's a yes?" He asked breaking the kiss.

With happy tears streaming down her face Elena nodded. "Yes, I love you so much!"

It had been two months since the night Stefan proposed. Elena stared happily at her princess cut platinum diamond ring. They decided they would hold off on the wedding for a year to give them both plenty of time to plan, for they were both busy with their careers at the moment. Elena was the sole owner of her parent's gallery. She was immensely grateful for her friends, Caroline and Bonnie, who both worked with her and helped out immensely. Stefan was now living with her as well and she was thankful for that. She hated being in this house all by herself.

Elena was in the kitchen of her house when the doorbell rang. She looked at the clock… 7:30am. Who could be here so early? She wondered. She wiped off her hands and shut down the stove, so her bacon and eggs wouldn't burn.

When she opened the door all she could do was stare. Before her stood the most gorgeous man she had ever seen. He had raven locks that flowed down in waves across his forehead. Chiseled cheekbones and soft full lips that Elena decided would be worth taking around for a taste test. Then his eyes… Elena thought she could lose herself forever in this all too familiar blue orbs. Oh my god! Elena what are you thinking? You don't even know the man – and you're engaged! Must remember you are engaged… wait a minute why does he seem so familiar?

The man smirked at the woman before him, all too aware on how she was studying him. He thought she wasn't too bad herself.

"Hi." Elena stumbled. Way to go Elena, make a complete idiot of yourself.

"Hey gorgeous, I'm looking for Stefan Salvatore."

Elena blushed and then she instantly recognized his voice and broke out in a wide grin.

"Damon? Oh my god! How are you?" She grabbed him in a tight hug then pulled away, and blushed a slight pink because of her earlier ogling him. She smirked when she looked up to find his confused expression.

"Elena?" he asked squinting. Wow, she really grew up to be a beautiful woman, he thought.

Elena playfully punched him in the arm for his playful squinting and invited him in.

"Still wearing your same old signature clothes I see." She smirked as his eyes grew wide and looked down at his outfit. Black fitted jeans, black fitted t-shirt. He honestly didn't find anything wrong with his choice of clothes. Before he could make a comment, Elena spoke.

"So how've you been? What are you up too?"

"Well me and the dear old man finally came to blows and I quit the company," he said not feeling one bit sad at his choice. He lived in New York where he worked for his father for Salvatore Corps. He never blamed his brother for not wanting to work for the bastard. They walked into the living room and sat down on the couch.

"Oh no, I'm sorry. " Elena said sadly, even though she knew Damon despised his father.

"Yea…"he said, then looked up into her brown doe eyes, "I'm sorry I wasn't there when you parent's passed… I know how it feels." Even though his father was alive, Damon knew what it was like to lose a parent. Especially a mother.

Elena nodded her head and looked away, tears threatening to well up in her eyes. Before she could say anything Stefan walked into the room, freshly showered and shaved.

"Hey sweetie, who's here?" Stefan asked, and then spotted the raven locks. "Damon is that you?" He grabbed his brother into a hug and patted him on the back.

"Your still a softy." Damon said with a wide smile.

"And you still look like a wanna-be vampire." Stefan shot back. Damon smirked at that.

"Hey, I'm sorry about what went down with you and the old man." Stefan said sincerely. "Is that why you're back in LA?"

"Yeah, I can't seem to get a decent job. I swear that bastard is doing this to me." Damon mumbled angrily.

Elena, who had been listening to the exchange the whole time, finally spoke up.

"I know! I could use some help at the gallery; a lot of help. I could really use some help with paper work and all that fun stuff you can work there… that is, if you want?" Elena offered with a huge grin on her face.

"You mean work for you?" Damon contemplated about it for a few seconds. "Okay 'Lena, it's a deal." They shook hands in agreement.

Elena smiled and looked Damon up and down. "There's one condition..."

Damon raised an eyebrow, waiting for the "condition."

"You can't wear that." Elena smirked at his expression, causing Damon too look down at himself with a confused look on his face and a snickering Stefan.

"Why the hell not?" he asked with a make-believe hurt expression.

Stefan clapped him on the back, "Well, you can always borrow my clothes for now."

Damon looked at him and burst into a fit of laughter, an amused Elena watching them.

See your face every place that I walk in
Hear your voice every time I am talking
You will believe in me
And I will never be ignored

I will burn for you
Feel pain for you
I will twist the knife and bleed my aching heart
I'll tear it apart

A month flew by, and Elena was becoming more accustomed to the events in her household. Damon now worked for her full-time and she had to admit that he was a good worker, he sold more paintings and artifacts then she ever did when she first started working at the gallery. Elena was shocked of his knowledge of the many rare artifacts on showcase. When Elena asked him where he learned everything from, he just shrugged his shoulders and winked at her.

Elena hated not getting a straight answer, but dealt with it anyway. It was now three o'clock in the afternoon and Elena was exhausted from the day's work. She told Caroline and Bonnie she was closing early and for them to go home. She went into the back of the gallery and settled into her office when her cell phone rang.

"Hello," an exhausted voice murmured into the phone. "Hey Stefan, yes everything is still on for tonight… no they don't have a clue… yes I will… okay sweetie I just have to wrap a few things up and I will be home to fix everything, k? Alright…love you too." Elena clicked her phone off and leaned into the chair.

"Hello cutie."

Elena shrieked and jumped out of her seat. "Damn, Damon don't you ever knock?" She said obviously annoyed her heart pounding in her chest. Damon rolled his eyes at her and smirked settling himself into her chair. He lifted his feet and threw them on top of her desk. Elena swung his feet off and muttered angrily.

"I am having a bad day right now and I don't need you adding into it!" She glared at him.

Damon was a little taken aback at her outburst. "Sorry, didn't realize you were in such a pissy mood." He noticed she was still glaring while rubbing the back of her neck.

"Something wrong 'Lena?" He asked, concern evident in his voice.

"Yeah I got the worst crick in my neck." She continued to rub her sore spot. Before she knew what was happening, Damon jumped out of the chair and pushed her into it. His gentle hands began rubbing her sore spot. Elena tried to protest but all she could muster was some incoherent muttering. God his hands feel so good, I don't want him to stop. God Elena what are you thinking! Elena immediately jumped away from his ministrations.

Damon was confused for a second and looked at her flustered form.

"I'm sorry if I did something wrong," he said still confused.

"No, it's not you!" She saw Damon flinch not realizing she had yelled. She blushed under his intensive gaze. He walked up to her like a tiger trying to catch its prey. Elena's heart pounded in her chest. What is he doing? What is he doing!

Damon saw how nervous she was getting and backed away. Elena sighed in relief.

"Elena, do you remember when I left for New York?" Damon asked inching a little closer to her.

Elena remembered. She was thirteen and he was sixteen, and they both had insane crushes on one another but never did anything about it. She always figured it was because she was young so she never dwelled on it. And before long she ended up falling in love with his younger brother. That was also when Giuseppe, their father, decided to send Damon to New York to a boarding school, cause Damon was wreaking havoc then.

"Yeah I remember, why?" Elena asked trying to keep her voice steady, but failing.

"Remember I wanted to tell you something but never got the chance?" He asked looking intently into her eyes.

Elena just simply nodded wondering where he was going with this.

"What I wanted to say was that… I was hoping whenever I came back… um… That there might be a chance for us," he slowly said and looked away from her confused and bewildered expression. What the hell! Whatcha go and say that for you idiot!

"Oh my god! Damon, why are you doing this now of all times?" Elena flung her arms around, muttering angrily.

Damon grabbed a hold of her hands. Elena tried to pull away and was forced to look into his eyes.

"Elena I was hoping…"

Elena finished his sentence for him. "That we could be together," she mumbled.

"Exactly, it's almost like you're reading my mind." He smiled softly.

Elena pulled out of his grasp. What an asshole! I can't believe this! He knows she is engaged to his brother what the heck is wrong with him? Stefan would kick him out in a heartbeat if he knew about this!

"Well why don't you read mine?" She looked at him sternly and put her jacket on and brushed past him.

He grabbed her arm before she could leave her office and turned her to face him. "I can't just be your friend."

Elena pulled out of his grasp and glared at him defiantly.

"I will see you at home, and if you ever and I mean ever bring this up again I won't think twice about telling Stefan," she said through clenched teeth.

Please review to let me know what you think! Also there will be flashbacks to when they were younger, but it won't be till a couple more chapters!