It was a million tiny little things that, when you added them all up, they meant we were supposed to be together … and I knew it. I knew it the very first time I touched her. -Sleepless In Seattle

I never planned on becoming Damon Salvatore's personal assistant. It's not like I woke up one morning thinking Hey, I know what sounds like fun, I want to follow that multi-billionaire who's in the tabloids every other week around for the next five years. But that's exactly what I ended up doing, I just sorta fell into it.

We met in the most ridiculous meet cute way, and if it had been a scene in a major motion picture I probably would of ended up with the husband and the white picket fence at the end of the movie, instead I ended up with the best and worst job of my entire career history. I became a PA to feasibly the most gifted CEO of my generation. Well, the job title says PA, in reality I was a laundry list of things for him; secretary, cook, first aid, counselor, mind reader, mother, sister, confidante but never ever ever something remotely romantic. Until one day everything changed.

And it all started with a glass of red wine.

"Seriously?" I mutter, as yet again another yellow cab whips past me splashing my ankles with stagnant rain water in the process. I'm a fresh out of college transplant from Virginia and I still haven't mastered the whole hailing a cab thing the native New Yorkers have down to a tee.

I've been at my new job for exactly two weeks, my first real job thats not slinging pizza slices, and I'm already late to the mandatory soiree they're holding tonight. The head of the company is coming down to say hello to all us little people and I guess we're all expected to be there to line up and kiss his hand or something.

After I spit out every curse word under the sun, one of the cab drivers finally takes pity on the girl who looks like a drowned rat and stops for me. After I get in I watch as the neon lights flash by, blurring into one long snake of illumination, and yet again I'm struck with how much bigger than me this all is. I'm nothing but a speck in New York, and I'm already pretty convinced I'm going to be eaten alive out here.

When we pull up to the Salvatore Corp. building with it's grandiose Art Deco facade I quickly pay the fare, never quite knowing how much to tip and step out onto the sidewalk. The lobby is deserted and I stand there for a moment dripping puddles onto the immaculate jade marbled flooring, still too new to find my bearings instantly. I locate the coat check and wring out my hair as much as possible, feeling like a human sponge, before I progress to the second floor.

The scalloped light sconces have been dimmed causing the room to be bathed in a soft golden glow, transforming the area completely from what I was used to during the day. Instead of harried work colleagues running around, waiters had taken their places smoothly slipping to and from the small groups of people that had formed, holding their serving trays aloft. The front wall is all glass from celling to floor, showcasing the twinkling New York skyline, the Empire State Building providing the main focal point in the vista. I'm transfixed for a moment by the sharp pinpoints of lights contrasted against the black of the night before shaking my head and swiping a glass of wine from a passing tray, holding onto the stem tightly as a means to ground myself.

My first order of business is to find Caroline in the melee. Caroline Forbes was my first and so far only friend in this city, she started work here the same day I did and after finding out we were both from similar small town backgrounds we have been joined at the hip. We're like the blind leading the blind though, one day we tried to find our way to the Statue of Liberty and ended up getting lost on the subway system for over five hours.

On the surface she's a typical effervescent blonde, who comes across as a little ditzy and maybe even slightly shallow. Take the time to dig under the miles of blonde curls and pink lipgloss however and you come to realize she's got a razor sharp mind and is sweet and loyal as the day is long. And she will definitely be my anchor to get through tonight.

I start to walk over when I think I catch a glimpse of her on the other side of the room and with my usual grace I plow into the chest of the first person who moves in front of me. With growing horror in the pit of my stomach I watch in slow motion as the crimson red wine from my glass overflows all over the man's pristine ivory dress shirt. The claret spill blooms and spreads like blood and I cringe as I raise my head to meet my victim's stare. The most flawless, clear blue eyes are looking back at me and the pleasant wooziness I start to feel has absolutely nothing to do with alcohol.

"I am so, so sorry" I profess, mortified to the roots of my hair. The man steps back and I can now see his eyes, stunning as they are, do not do the rest of him justice. His ruffled onyx hair provides the perfect contradiction to his alabaster skin and the smirk he is currently shooting my way is positively sinful.

"I wouldn't worry about it, I'm used to women losing their motor skills in my presence" He assures, cocky as hell. He holds the damp ruined part of his shirt away from his skin with two fingers.

I suppress an eye roll and smile tightly back at him. He may look like he walked off the cover of a magazine but I'm just not the type of girl to fawn over male model characters who think smarminess is the way into any women's panties. My estimation of him plummets, I gather he's probably a middle management type at the company, kept on the payroll to seduce the female clients into signing a contract with us.

With a confident move he's probably performed a thousand times before he takes my hand and kisses it. "No harm done" he declares and then he disappears again. I'm left standing with my drink dripping over my hand and mulling over what just occurred.

Caroline bounds up from behind me and I regale her with the whole embarrassing tale, once she hears how attractive the guy was she begins to search out the crowd for him like a sniper picking out it's prey. The girl is on a mission so I leave her to it while I go to freshen up my make-up. I swerve the nearest bathroom knowing it'll be jam-packed and venture further down the hallway to the executive one, figuring no one will be around to stop me from using it.

As I enter I see the man I just dive bombed with alcohol leaning over the sink, topless and scrubbing furiously at the stain on his shirt with a bar of soap and hot water. I have to force myself to drag my eyes away from the expanse of his back which is rippling with knotted muscles and I feel a acute sting of guilt at what I did to him.

"You're just going to imbed the stain more" I inform as I take pity and gently remove the shirt from under his hands. I hold it up to the light trying to get a read on how bad the discoloration is.

"Fuck" He curses violently. "My assistant left to have a baby last week and I've been helpless ever since. She's always the one that knew how to fix this shit".

I suddenly notice the shine of vulnerability in his eyes that definitely hadn't been there before and the guilt I'm feeling ratchets up to a new level, he's probably terrified he's going to get fired or something with the CEO making an appearance tonight.

"Wait here" I instruct as I rush back to the main party and grab the items I need. I return and pour some club soda and table salt on the stain and rub at it until it begins to fade away, and then utter relief as it fully goes. I hand it back to him and he looks at me impressed.

"Thanks" He beams as he holds the top under the hand dryer, waiting for it to dry. "What's your name? I don't think I've seen you around before"

"I'm new but it's Elena. Elena Gilbert" I see him silently repeat the name back to himself like he's committing it to memory. "And yours? I haven't seen you around either. Do you work up on the marketing floor?"

Sheer amusement spreads across his face as he digests my words, and I'm left feeling like I'm missing a huge private joke. As he slips his shirt and tie back on he answers smugly. "Just some guy, that's all. Just some guy".

He leaves me standing alone yet again, and suddenly I'm feeling very sorry that I lifted a finger to help him at all.

Caroline and I spend the majority of the evening gorging ourselves on tiny canapes and wrapped olives when all I really want is a fat greasy burger. Finally, the man of the hour decides to grace us with his presence and we're all herded to stand before a raised make-shift stage. Caroline starts to bounce from one foot to the other and I lazily stare around the room, yawning and waiting for the speech to start.

I hear a finger tapping on the microphone and a short balding man I recognize as one of the members of the board introduces "our illustrious leader" and out walks my boss's, boss's boss. None other then Mr. Red Wine. The man who I had the nerve to ask if he was in marketing, does in fact own the whole fucking company. I start to get a little light headed and try to discreetly wave my hands around to get Caroline's attention as he starts speaking.

She looks at me and I point at him and then mime spilling a glass over him. Her eye grow wide as what I'm trying confess hits her and right as I'm pulling a ridiculous face I realize the whole room has grown silent and has turned to face me, mid imitation and he is looking at me perfectly politely waiting for my attention.

"If Miss. Gilbert has quite finished with her energetic retelling I would like to continue if that's acceptable to her" He announces, clearly and succinctly to the whole entire room.

I'm calling him every bad word my parents never let me use in my head as I nod and blush all the way down to my toe nails. And then as if someone pushed a button everyone once again turns back around and focuses on him as he finishes and promises us all another profitable year.

Isabelle Fleming, one of the women who works in a cubicle next to mine is already talking to Caroline as I sidle up. Isabelle has a few years on us at the company and she seems to take this as carte blanche to demean us anyway she can, she's one of the snidest people i've ever had the displeasure of meeting.

"So Damon Salvatore knows you by name, you must feel special" She drones at me, probably peeing her pants in happiness at the humiliation he just caused at my expense.

"We met..briefly" I deflect, trying to count down the seconds until I can go home, dive under my covers and pretend the whole night never happened. After prattling away for ten minutes Isabelle finally leaves us alone to annoy some other poor soul and I'm finally free to talk to Caroline.

"You had no idea who he was?" Caroline questions, looking shocked.

"Nada, I was expecting some decrepit old man to be our CEO. He's what? In his late 20's?" I took the first job that was offered to me in New York and now I was paying the price for not finding out the history of the company or of a Mr. Damon Salvatore.

Caroline shrugs "I think he was some sort of child prodigy or whatever. He inherited the company when his dad died a couple of years ago. I mean I don't know much about him but I know his name and face. He's always in the papers...for varying reasons"

"Oh" I responded dumbly.

"Yeah, Isabelle said he was featured in this week's Time magazine, he's like unbeatable or something"

Except for when he needs to wash his own clothes I think vindictively to myself. On the way home against my better judgement I dip into a open all hours news vendor and pick up a copy of Time magazine. After all, if I want to succeed at my job I should probably learn some of it's past.

I flip through the magazine under my covers with a flashlight, like I used to do when I was twelve and read Cosmo without my parent's permission to find out all about boys. Except this time I was finding out about one very specific boy and I couldn't shake the feeling I was doing something wrong.

I deliberately skip past his photo spread and start studying the word heavy article. It starts by repeating basically what Caroline had told me earlier, he was a exceptionally intelligent child who excelled at whatever he put his mind to. Graduated with a doctorate from Harvard and then took over the now infamous advertisement company when his father passed away. I start to skim when the article starts just repeating words like mogul and tycoon to describe him and find myself drawn to the last paragraph which briefly touches on his private life. He has a younger brother- no name given, is very close friends with his attorney by the name of Alaric Salztman and is allegedly single. It finishes by making a witty comment about Damon's work dedication and impeccable reputation despite his womanizing ways. I roll my eyes, womanizing ways- color me shocked.

I wake up the next morning groggy and with the magazine sprawled open across my face, obviously having fallen asleep during a re-read. Wanting to make a good impression after the debacle of last night I take a quick steaming shower, pull on a blouse, pencil skirt with nude stilettos and arrive early at my cubicle.

I'm pretty low on the food chain here, a paper pusher for lack of a better word and as usual I find myself distractedly spinning on my chair and gnawing on my pencil as I wait for the lunch hour to come. The phone on my desk, which literally hasn't made so much as a peep since I started working here abruptly comes to life, shrilly cutting through my daydreams and almost making me fall off my chair.

"Hello, Elena speaking" I tentatively answer.

"Please hold for Mr. Salvatore" A cool, pleasant female voice comes through the line. I start to panic, surely he's not going to be petty enough to punish me for the incident. I idly wonder if he had told my superior about the events of the previous night.

Before I have time to deliberate further his already familiar velvety graveled voice starts to drawl. "Miss. Gilbert, I trust you made it home safely last night"

I grind my teeth before replying, I can hear the smirk stretching across his face as clearly as if I could see it if he was sitting in front of me. "I did thank you Mr. Salvatore" I state, snippier then I perhaps should have considering he can kick my ass out onto the street on a whim.

"Please clear your lunch hour today for a meeting with me, I would like to discuss some things with you" It's more of an order then a request.

My mouth dries, what possibly could he want with an insignificant employee barely on his radar? I can't help but ask "Lunch hour today, why?".

"Just make sure you're there. Probably should take more than an hour off too, it may overrun"

"I don't know if I can take the time off, I have a lot of work to complete" I say as I look at my wire inbox, which is mockingly empty, forgetting for a second who I'm talking to.

He laughs "I'm pretty sure your boss will be okay with it"

I flush, of course my boss would be okay with me staying out late for lunch if the order came from their boss. "Alright" I agree meekly.

"Mary-Ann will give you the details". And then the line clicks and his perky secretary is back on giving me directions and the name of the restaurant we're supposed to meet at. I recognize the name, it's the kind of restaurant you have to be on the waiting list months to get reservations.

I spend the next hour hiding in Caroline's cubicle talking about why he possibly would take me out for lunch if he's just going to fire me. Caroline gloomily ponders if he gets his kicks by humiliating young girls at expensive restaurants, she's such a mood lifting person.

Dana, a nosy but nice enough girl sticks her head over the separator. "I'm surprised he's even still here today. He's usually jetting off to somewhere exotic, he never spends a lot of time actually in the building." Caroline studies my face for a minute then goes back to concentrating on painting her nails.

Finally the time comes and I swipe my pink lipstick across my lips and decide that's as good as it's going to get before walking down the sidewalk to the restaurant which is only seven buildings away. Just as I'm about to enter, palms sweating, this time it's my cell that starts to ring.

"Hello?"

Great, Mary-Ann sunshine is back. "Mr. Salvatore wished for me to inform you that he unfortunately can no longer make lunch but would like you to join him for drinks at the same place tonight"

Can you say power play? Waiting till the last second to let me know about the change in plans? For a brief moment I wonder if Damon arranged this from the get-go so we would always end up having to meet at night. I sigh and consider refusing, it would mean cutting into my own personal time but I acquiesce just to get it over with. I somehow know Damon would of gotten his way anyways. "Fine, i'll be here at 8:00"

I really shouldn't do it, but I do it anyways, I intentionally turn up twenty minutes late to the restaurant that night after deciding that Mr. Salvatore needs a small taste of his own medicine. It's a dangerous game but the little thrill I get when I see him already stoically waiting for me is worth it.

Without acknowledging my tardiness he rises and greets me and my nerves are back with a vengeance when I realize exactly who I'm about to spend my time with.

"What can I get you to drink?" The waitress directs her inquiry at me but doesn't take her eyes off Damon, I don't really blame her.

Flustered, I wave my hand towards Damon's glass tumbler "Whatever he's having". I catch Damon raising an eyebrow at me but he chooses not to elaborate.

I get the impression he wants me to break the silence first, so I do. "Just some guy huh? You could of filled me in before I made a total fool of myself"

"I didn't know if to believe you at first, not a lot of people don't recognize me" he chortles teasingly. "Though it soon became clear you were completely clueless about my identity"

"Well" I huff, cutting straight to the point "What is it that you wanted to talk to me about Mr. Salvatore?"

"I was impressed with the way you handled the situation last night. I want to offer you a trial run as my assistant. My PA"

"This is a job interview?" I question, astounded. All I did was clean a simple shirt for him, it's like housekeeping 101.

"If that's what you need to call it, I guess. You're very straight forward and breezy with me, Miss. Gilbert, It's refreshing. Not a lot of people interact with me the way you do"

I hadn't realized my inherent sassy attitude and aversion to authority figures was a positive thing. "But I already have a job"

"Is it your dream job?"

"I suppose not, but not many people get their dream job straight away do they?"

Grinning, he shrugs "I did. You can't tell me you actually like what you're doing right now."

"You don't even know me, I could be the worst PA in the history of PA's"

"I just have a feeling about you" he proclaims. "And as for not knowing you, that's what tonight is for"

As if on cue my drink is served. I take a careful sip of the caramel liquid and almost spit it straight back out onto the tablecloth. "How can you drink that, it's tastes like lighter fluid" I exclaim, revolted.

"That is 30 year old scotch Miss. Gilbert. It's an acquired taste"

"One I never hope to acquire" I mutter. "So, what does the 'most prolific young entrepreneur in the Big Apple today' want to know about me?" I realize my mistake when it's too late.

"I see you've been doing some research of your own. Quoted straight from the Time's article wasn't it?"

Of course the man knew each and every bit of press he received by word recognition. "Just doing my part in keeping my knowledge up to date"

"Mmmm hmmm, if that's what you need to tell yourself. So, tell me about you, what was your childhood like?"

I take another gulp of the abhorrent scotch because I need something to smooth the rough edges of the night down, the whole situation is mystifying. "There's not much to tell, I had the typical all-American apple pie lifestyle."

"Uh uh, you're not getting off that easy. You have a cheat sheet with me, it's all online. But you are a conundrum" he notes before leaning forward over the table and hitting me with an intense gaze. I suddenly realize partly why he's so successful, he has this way of making you feel like you're the most important thing in the room to him.

I relent and start to list the factoids of my fairly humdrum life so far. " I grew up in Mystic Falls, Virginia with my parents and younger brother, all of whom still live there. I got my degree in business at UVA and then I came out to New York, got a job and here I am having dinner with you".

"Why New York?' He questions with unnerving laser insight and perceptivity.

I take another bitter mouthful of my drink, this question always stings to answer. "I wanted to get out of Virginia, it was the first place my finger landed on the map".

Predicting what his next question will be I carry on before he can voice it. "I was a ballet dancer, I trained my whole life and got accepted into the Royal Ballet Company in London. About a week before I was due to leave I was doing a performance and fell in a weird way, shattering my right femur and the bones in my ankle. It healed okay enough, and I can still dance casually if I wanted but it becomes too painful to train any longer then for an hour so my dreams of going professional were well and truly out the window. So after college I wanted to leave all that behind"

Instead of the sickly look of pity I was expecting from him, he only shrugs and observes "At least you went out in a blaze of glory".

I suppose most people might of hated him for a callous remark like that, but for me I can pinpoint it as the exact second I decided I liked the guy. He was an optimist, in a dry, biting humor kind of way. The fact is, not becoming a dancer hadn't made me bitter or against the world and it was something I wasn't going to let stain my future. It was nice to meet someone who didn't treat me like I lost the only important chance I was ever going to get in my life. "That's one way of looking at it I guess".

The drinks came quicker, and I started to become numb to the the taste of them. We had soon progressed to first name basis, and I began to view Damon as a person, not just as a suit. He was wickedly funny and astute, liked to cut through all the bullshit and just say what was on his mind, and after the second hour I spent with him it didn't even enter my thoughts that I wasn't drinking with a old friend.

"No you ass, I will not do a ballet move in the middle of the restaurant for your amusement" I proclaimed, trying not to laugh at Damon's new request. The fact I just branded him an ass with no hesitation spoke volumes on how far our banter had actually advanced.

"So your brother, does he work at the company too?" I ask, switching topics.

Damon noticeably sobers and shakes his head. "No, haven't seen him for years to be honest"

I cross and recross my legs nervously, sensing I have hit a nerve. I'm reaching for something else to talk about when to my surprise he starts to explain.

"Can I trust you not to go running to The Enquirer tomorrow morning with the story?" He cautions, looking serious enough for me to sit up and pay attention.

I do the sign of the cross on my chest "Cross my heart and hope to die"

"My brother ran off with my fiancée four years ago, the socialite Katherine Pierce?"

I shake my head to indicate i've never heard of her and try to ignore the twist of compassion I sharply feel for him. "Wow, that sucks" I acknowledge lamely.

My sharp observation at least gets him to raise a smile. "Yeah, you could say that. Took a lot of lawsuits to keep that scandal from becoming public knowledge. And here I am spilling my guts to you"

"Must be something about my face" I joke. "You never thought about trying to get back in contact with him? Is it worth losing a brother over some girl?" The words have slipped out before I realize I just crossed a hell of a lot of lines. "Oh my god, that was beyond inappropriate of me, I'm sorry"

He waves his hand and laments "We've shared too many drinks to worry about being inappropriate. Don't get all weird around me now, it's been a long time since i've been able to have a frank conversation with someone"

I think about how everyone he comes in contact with must want something from him, and how empty a life like that must be, it makes me warm to him even more. After catching sight of the time on my cell I pull a face "I really should get home, it's getting late. I had fun tonight though". It seems we had both forgotten the actual reason for the meeting at this point.

"Yeah, so did I" He smirks and insists on paying the bill, helping me out of the door after I find out I'm a lot more drunker then I had previously fully appreciated.

We pause in the outside alley as his inhales on a cigarette and puffs the smoke back into the air. "So how about the job then? You'll get to see the world, it can be on a trial basis and if we decide it's not working out you can go back to your cubicle"

Why me? I want to ask, but to be truthful I don't even think he really knows. I've never been the spontaneous type but i've lost enough opportunities not to at least give this one a serious try. I find myself agreeing to his proposition without really even hearing what it fully entails. "I think you've plied me with enough booze to get me to say yes".

A real genuine smile spreads across his face and he nods once distinctly. "My first request of you as my assistant is to show me your ballet skills, just once" he pleads.

I smile and purse my lips but in my alcohol induced haze I rise to en pointe and perform a impeccable arabesque in that grey, dank alley, my right leg pointing to the sky.

We both dissolve into fits of laughter at the same time and he catches me in his arms as I move back down. I know what he's going to try before he even knows he going to try it, so as he leans in and searches my eyes I place a finger to his lips, pushing him gently back.

"Woah flyboy, if I'm going to be working for you, I won't have you regretting making drunken mistakes with me." I smile at him to let him know no offense is taken. I don't want to be treated like one of his conquests, i'd actually like to gain his respect and become a friend, and I know making out with him is not be the route to take, even if a tiny corner of my brain is screaming at me for rejecting him.

He grins surprised but unaffected, slings an arm around my shoulder as he steps on his cigarette and moves me towards the street. And just as I'm getting a strong whiff of his aftershave my stomach whirls and I remember why I have a strict self imposed 4 drink limit. I rip myself away from under his arm, barely having the time to yank my long brunette hair back from my face before I turn and empty all the contents of my stomach onto the gravel.

One time in first grade I peed my pants in front of the whole class, and this? This is about seven levels of hell above that. It comes to my attention that Damon has replaced my grip and is now holding my hair in a low ponytail and holding out a tissue for me. I dry retch once more, wipe my mouth with the back of my hand and accept the kleenex. "Thanks" I say, tartly as I can considering the man just watched me vomit.

"No problem" he declares. "Not everyone can hold their drink like me".

I bite my lip to stop myself from crying and I'm probably redder than a whore's lipstick. "Oh god, I'm sorry" I stutter, humiliated. "I totally understand if the job offer has been redacted"

He starts to howl laughing "Nah, we've both made fools of ourselves tonight, if anything it makes me like you more. You haven't really bonded with someone until you've watched the other person throw-up". His arm goes back around my shoulder "You start tomorrow, bring aspirin"

God, if I had only known what I was about to get myself in for.