She looked into the eyes of the only man she's ever loved and realised the amount of pain flashing through them and shuddered .

"Fine , explain! Explain how everything went so wrong for you .. " she asked him taking in shaky breaths.

"Please Damon , just tell me why."

...

Elena Gilbert did not fall easily for a mans charm and smile, but the night she met Damon that changed . It had been two days since she had experienced one of the most amazing dates ever , although she had to admit she was more nervous than excited for the next one.

"So! Bet you're glad I convinced you into that double date now aren't you!" Caroline squealed as she walked into her apartment.

"Ok first off yes I am actually and two can you dial it down a bit it's 8am and I'm still in zombie mode." Elena grunted grabbing a glass from the cupboard.

"Arggg why are you such a crank in the mornings! It's so annoying I want the old energetic Elena back!" Caroline whined.

"That Elena died a very long time ago ! I start my shift in less than an hour so forgive me if I'm not all sunshine and rainbows !"

"You're no fun! But anyway are you and Damon still going out again? Or do I have to go through my list of potential boys ?" Caroline asked making herself a coffee.

"Well he hasn't called because of work but he did text me yesterday, only a small hi it's Damon save my number but it's something right !" Elena chirped , smiling at the thought of the handsome man she'd set her sights on.

"It is indeed ! Stefan said he's never seen Damon this interested in someone before !" She smiled widely at her friends reply and grabbed the orange juice from the fridge .

Elena has never let her self be in a serious relationship since Tyler , Tyler was great but she couldn't see herself ever falling in love with him. Too much had gone wrong with them even in the short year they was together .

Truth is she was scared , commitment really was the one thing she couldn't get her head around . Maybe it's because she hasn't been in love yet , she had loved Tyler but she wasn't in love with him.

"I really like him , I just hope the next date is as good as the last." She spoke her words softly as she took a sip from her glass.

Caroline sighed softly and reached out to grab her friends hand.

"Look , I know you're worried after everything that happened with Tyler but you'll be ok. Damon is smart, attractive , mature , he's not an immature boy like Ty was ." Elena smiled at her best friend and sighed.

"You're right , no matter what thoughts are going through my head Damon is amazing and I will be fine . It's about time i gave my self a chance at love."

Two hours later and she was back again,stuck in work with sweaty old men perving at her as she served other customers and passed around their food. She really hated how her life had planned out , but she didn't have enough money to go back to college yet.

The whole reason she hadn't gotten chance to finish her medical degree is because her father had passed away leaving her baby brother Jeremy alone back home . That meant she had to drop everything to go support him! but now 2 years later he's at college himself and she's stuck in a dead end job with no support from anyone to help her get back to college, it sucked really.

"Why so glum beautiful?" A familiar voice chirped making her head shoot up.

"Damon?! Hey what are you doing here?" She questioned him in shock.

"Well I don't know about you but I always found arranging a date over the phone to be less romantic." He said smirking .

"Well Mr Salvatore it's just your luck I'm about to have my lunch break. Take a seat."

She watched as his perfect self walked towards the small booth across the room and she felt he knee's go weak.

"Soooo , is there a new boy toy on the seen?" Her boss and Caroline's mother Liz said chuckling.

"Nope , new Man Toy Liz ! He's all man ." She said smirking as she grabbed her lunch and made her way over.

She was glad she decided to wear her hair long and straight along with her short black skirt and red blouse . It's a little more appropriate for a lunch date than the original sweats and baggy T she first had on.

"Nice skirt, no wonder all the old men like it here !" His voice pulled her from her thoughts and she laughed softly sitting across from him.

"Thanks , I wish that wasn't the case though but still thank you."

"You're welcome , so how about 7:30 tonight that's a reasonable time for you? "

Elena coughed and looked up in shock.

"Ermm, yes! Sorry I just wasn't expecting you to ask straight away!"

"It's all good ! But 7:30 I'll come pick you up , oh and Elena ? Don't look so nervous I promise I really do like you ." He smiled softly standing up and kissing her cheek .

"I like you too, bye Damon." She said smiling softly as he winked . God she has no idea what this man is doing to her but she definitely enjoyed it !

Liz walked over just has he exited through the door and sat with her.

"He's most definitely all Man! Is that Damon Salvatore as in the Mr Salvatore editor at Joulsburg books !"

Elena blushed and looked down.

"Maybe... but hey your daughter is dating his brother ! You know he's just as manly."

"Yes , but he's also my possible son in law ... so I can't exactly say much except he's got a good career ! Paramedic isn't he?" Liz questioned.

"Yeah and he's literally perfect for Caroline , have you met him yet?" Elena asked .

"No ! You know what Carebear is like she won't introduce us until she's prepared him." Liz said laughing.

"That is true! But hey I promise he's amazing you're going to love him."

"I trust you Elena , Damon though ? What's the deal you two official or just dating ?"

"Oh ! just dating ? I guess .. I mean we met 2 days ago and tonight is our second date." Elena mumbled biting her lip.

Liz smiled softly , pushing a stray piece of hair behind her ear . Elena never had a mother growing up so Liz was all she had . Liz had watched her struggle through everything and was nice enough to offer her job as soon as she returned to California.

"Elena , you'll be ok ! Stop worrying that pretty little head of yours . Damon is a business man he knows what he wants and he wants you ! Embrace it . Find your Epic Love , it's about time sweetheart..."

The first thing she done when she walked into her apartment was get a shower. Working in the cafe always puts her on edge about her appearance once she leaves that place . No offence to Liz but working with coffee and grease all day just isn't something she enjoys along with the smell that comes with it . She waited as the water began to heat up before slowly stepping inside .

The water splashed onto her skin making her shiver at the contact before she allowed it to dance over her skin and through her hair. She decided on her blueberry scented shampoo , that had always had an effect on people's noses it was a strong and pleasant smell. Showering had always been one of her favourite things to do , she loved the way her body just relaxed and felt free. The shampoo massaged her scalp and the soap made her skin tingle , there was nothing better .

She opened her eyes enough to catch a glimpse at the small clock on her bathroom wall, 6:45pm she best get her ass moving otherwise she wouldn't be ready . She grabbed a towel and wrapped herself before walking down the hall to her bedroom. Elena was quite a simple girl meaning her decorating skills where just the same , her bedroom was full of creams and pink along with a diamond lamp shade just to liven the place up a bit . She walked over to her walk in closet and sighed.

The first two times she had seen Damon she was wearing red , maybe it was time for something a little different . Maybe a nice blue will be the right choice , not too dark but not too light either .

She searches for about 5 more minutes until Bingo! Her eyes fell on her long gold dress and she knew it was the one. It's plain detail just made the colour seem even more gorgeous and it reminded her of Damon's eyes, he had these small flecks of gold inside those ocean blue lookers and she loved it .

"Crap hair!" She exclaimed to herself rushing to grab her hair dryer. It only took her about twenty minutes to finally finish her hair and makeup and she had to say she was looking pretty damn good! Her hair was curled and pined neatly up , her makeup was neutral but she was wearing just enough for it to seem glamorous.

She quickly slipped into her dress before grabbing her shoes and bag rushing into the other room just in time for the door to sound.

Pushing her feet into her shoes as quickly as she could she grabbed the door handle forcing it to open.

"Damon! You're five minutes early ?!" Elena rushed out seeing him stood in a suit .

Suddenly she felt as though she was underdressed , why was he wearing a suit?

"Hey ! Sorry I just decided to come I was out of work early and didn't want to just sit around ... are you nearly ready or?" He asked.

"Yeah! I'm ready just thought I'd have chance to grab a mint at least !" She exclaimed before blushing .

"A mint? Huh hoping for a bit of action are we miss Gilbert?" He said slyly.

"Oh hush Mr Salvatore! Where are we off to anyway ?" She said shutting the door behind them.

"Well , I have a gala for work and you my dear are joining me ... as my date ."

"What!" Elena shrieked.

"It's ok ! Trust me they're going to love you , believe me it's rare I even turn up to these things never mind with a date !" Damon assured her.

"Wow , ok you don't think I'm a little underdressed ?" She asked self consciously.

"No! You look unreal , honestly Honey you look amazing don't threat." He said grabbing her hand as they walked towards the elevator.

The ride to the gala was a short ten minutes and honestly that did nothing to help control her nerves . She was terrified, Damon was a big editor in California and most newspapers and magazines knew of him so being his date to an event like this was a very big deal!

"You ready to go in?" Damon asked gently.

"As ready as I'll ever be..." she muttered climbing out of the car door slowly.

Instantly she was met with the flashes of cameras and she raced to Damons side.

"What is with all the cameras ?! " she gasped.

"There is a lot of famous authors here tonight , don't worry though it's only a couple of pictures then they will move on to the next couple . " He replied slipping his arm around her waste and leading her to the carper area.

They posed for a few pictures before her eyes followed Damons to a familiar set of eyes.

"Father !" Damon called.

God she had no idea she would be meeting the family so soon.

"Damon! How are you my boy." The man who she now knew as the Salvatore Father asked approaching them .

"I'm good! How is everything here? Been ok?"

"Yes , yes! Everything has been fine don't you worry ... now who is this gorgeous thing you've brought with you ."

Elena felt her self shrink under his gaze , gosh as nice as he seemed he definitely knew how to stare you down if needed. His eyes where an exact match to Damon's she now knew why he was so stunning , you can tell his father would of been a looker back in the day himself .

"Elena, this is my father , Father this is Elena ... my date."

She smiled as he took her hand and gave it a gentle kiss on the back. She couldn't believe this was happening , she's never felt this important in her entire life .

"Pleasure to meet you Elena , please call me

Giuseppe!" He said smiling brightly .

"Nice to meet you too !" She replied smiling cheerfully.

This night was going to be better than she thought !

A/N : I will be editing each chapter once the story is finished so please If you notice any mistakes let me know!