AN: I'm back! First off, just to warn you readers, this is going to be a fluffy fic! Also, if you recognise the plot from the summary it's because I'm writing this fic based on the movie 'How To Lose A Guy In Ten Days'. (Seriously, watch it!) I'm using the storyline but obviously I have a different article but there will be some scenes from the movie! Hope you enjoy!

Also, I'm looking for a pre-reader who would just read the chapters and make sure everything flows and can correct any little mistakes I might've missed during editing so if you're interested then please, PM me!

Disclaimer: I do not own 'The Vampire Diaries' or 'How To Lose A Guy In Ten Days'.

All outfits for this fic will be available at amygerrard . polyvore . com (without the spaces, obviously!)

Day One

Elena felt the wet tears stream down her face silently as she stared up at her white ceiling. She sucked in a deep, painful breath as she wet her dry lips with her tongue, licking away a salty water droplet from the corner of her pink flesh. She turned her head towards her alarm clock, the damp white fabric of her pillow case sticking slightly to her flushed cheek, and glared at the green digits blinking back at her. 6:13. Just two more minutes and she would be able to escape her bed at a reasonable, albeit earlier than usual, time.

She sat up in her plush double bed and swung her calves over the side. Her shoulders hunched as if the weight of the world was pressing down on her as a sob flew from her lips. Her fingers clenched her locket as whimpers tore from her throat and the tears fell freely from her eyes. Her chest felt tight, reminiscent of the night when she had lost two of the most important people in her young life. She gasped for air, much like she had done in her nightmare when only water had filled her aching lungs.

"Mom, Dad," she sobbed, her hand reaching unconsciously for the memory of her parents. She remembered how she had frantically tried to shake her parents as their car was submerged with water. Her efforts had been in vain, no matter how much she had tried to wake them from their slumber, they simply floated in the metal vehicle as their belts trapped them to their seats. Her hand had grabbed her throat as it burned for the much needed oxygen whilst her elbow thrashed painfully against the thick glass window.

Her attempts at escape had been futile and as her world began to blur around the edges, she let go of her hold on it. She swam forward until she was in between the two front seats as she grasped each of her parent's hands in her own. She breathed one last 'I love you' to her mother and father; the people who had raised her. Her mouth filled with water as each word passed her lips and infiltrated her lungs. Her eyes drifted shut as her consciousness faded into the welcoming darkness.

Elena wiped away the wetness on her cheeks and quickly blew her nose with a nearby tissue. She let out a soft sigh as she remembered her confusion when she had woken up in the hospital. A man, a brave man, had seen the accident and he dived in after their car. What had felt like hours to her had been only minutes in reality. The unnamed hero had managed to break the window with his boot and pull her safely from the wreckage. When he dived back under, he was unable to rescue them; the steering wheel was lodged against her father's chest and her mother's legs had been trapped by a large dent in the passenger side door. He had promptly called for an ambulance and taken her to the hospital, leaving the vehicle to be removed from the water by the police. He waited at her hospital bed until the doctors confirmed that she would be fine. And then, he left. No praise or thank you's were needed in his eyes and her safety had been enough of a reward.

She had woken up a few hours later after the water had been drained from her lungs. Jeremy had held her hand tightly in his own larger one as she roused from unconsciousness and they had fallen into each other's arms as they mourned for the loss of their parents.

Their lives had changed so drastically in the space of a few hours. Elena had been at a party getting drunk and was left stranded. Her parents had come to her aid and in doing so, had lost their lives. Jeremy had been making love to his girlfriend, Bonnie, for the first time when news of the accident had reached him. The once careless attitude of a twenty-one year old dissipated quickly as he became the legal guardian of his eighteen year old sister. What had started out as a fun night for both of the Gilbert siblings had ended in a heartbreak that would never be fully overcome.

Elena took deep, calming breaths before moving towards her bathroom. Once her feet met the cold tiles, her clothes fell from her body and littered the floor. She moved to the shower and scrubbed her body of the sweat and tears that had covered her skin; that covered her skin every year that this day rolled around. She would normally indulge the feeling of the warm water droplets as they pelted against her olive skin but not today. Today, she loathed the feel of the water on her skin. She cleaned her body quickly and efficiently, not even letting her fingers trail south and bring her the pleasure that helped her to start off the day.

Two minutes later, she emerged from the shower and wrapped one of her plush purple towels around her. She wiped at the layer of steam that covered her mirror and groaned at the sight of her puffy and bloodshot eyes knowing that no amount of make-up would be able to cover her despair. She towel-dried her body, taking extra care to ensure no water lay on her skin. Elena blow-dried her hair completely naked as she allowed the warm air to travel over her body and raise goose bumps on her skin. Her silky hair fell over her shoulders, caressing her flesh lovingly as it curled around her figure; somehow offering her the comfort that she craved.

Twenty minutes later, she slipped her chunky black heels onto her delicate feet. She stood up from her freshly changed bed and smoothed out her deep purple pencil skirt and adjusted her white blouse. She shrugged on her black fitted blazer and grabbed her messenger bag before exiting her bedroom.

With her fresh bouquets of lilies in her hand, she left behind the haven of her small apartment and stepped out into the morning chill of the New York air. She battled against the bustling winds as she threaded through the many streets of the city. Her feet followed the well-known pathway until she was met with the cold iron gates of the cemetery.

Elena rested her forehead against it in silent encouragement as her hand pushed the gate open gently. Her ankles wobbled on the stones of the pathway as she walked towards the familiar plots and she pulled the flowers closer to her chest as a gust of wind swirled around her small body. She stepped onto the grass as she found the particular row she was looking for and stood on her tip toes, trying desperately to stop her heels from sinking into the slightly slippy ground beneath her.

Her hand flew to her mouth as she saw the two granite gravestones that had their names imprinted on them; Miranda Gilbert and Grayson Gilbert. She dropped her messenger bag to the ground unceremoniously and immediately kneeled down on it to protect her outfit from the soil and grass covered in dew. She swiped at the green leaves that had fallen on the top of their gravestones before she placed each bouquet on the sodden ground.

"Hi Mom, Dad," she whispered, wiping at a stray tear that was threatening to roll down the length of her cheek. "Sorry, it's been a while. I've been a bit busy at work," she sighed. Her fingers traced the engraved letters as her mind swirled with memories. "Has Jeremy been to see you yet? I guess not," she chuckled, "it's still early and you know very well that he was never a morning person."

"I really miss you," she choked out, her head leaning against their cold gravestones as her eyes drifted shut from exhaustion.

"Elena, you're late!" Carol Lockwood exclaimed in a shrill voice as Elena burst through the conference room doors.

"I'm sorry, I was-"

"Frankly, I don't care about your reason. Make up the time later." Carol spat as Elena quickly sank into one of the plush chairs that surrounded the large, circular table.

"Sorry." Elena murmured as she took out her notepad and pen from her handbag. She raised her head slightly and surveyed the faces of her fellow employees. Her gaze soon landed on Caroline, her best friend from childhood, who sent her a sympathetic glance. She gave her a small and what she hoped was a reassuring smile in response before zoning in on the assignments that Carol had planned for the next issue.

Each employee was given a concept for an article, they voiced their opinions and ideas and were given a deadline. All in all, it was a regular, mundane Monday morning for Elena and the rest of the employees at Dazzle magazine.

"Caroline, I want a list of the ten must haves for your spring wardrobe," Carol, the executive producer, ordered.

"Should I include shoes and accessories, Mrs Lockwood?" Caroline questioned as her sparkly pen scribbled across her pink notepad.

"Yes, to the shoes. Don't let them overcrowd the list. Two pairs maybe, day and night. Accessories will have their own inset but keep the number to a minimum. Remember, two pages are all you get so use them wisely." Carol waggled her finger whilst moving her icy gaze around the room, a warning to everyone to not exceed their limit.

The warning was unnecessary; everyone remembered what had happened to Emma Reid. It had been her first week at Dazzle after her move from In Style magazine and she had fit in straight away. Her first assignment was going to be a real hit and the whole office was raving about her work. She had been given three pages, including the centre fold, but Emma said she needed just one more page for her article to be perfect. Despite our protestations, she went to Mrs Lockwood's office and asked for another page in the issue. Emma spent nearly an hour in the office as Mrs Lockwood proceeded to scream and rage at her, never allowing Emma to utter another word. The yelling could be heard throughout the whole building and when Emma finally emerged from the room, her face was streamed with tears and mascara. The next day she quit and everyone at Dazzle knew now to take what they were given with no complaints.

"Elena, our 'how to' girl," Carol smirked as Elena's expression lifted. "Let me guess, you have an idea."

"Well, I found out about these really inspirational women who use all of these various methods to reduce their carbon footprint and save money at the same time. It's something which would be very beneficial for everyone to learn about, especially with all of the climate change worries. I was thinking-"

"Elena, stop. This isn't what women in their twenties or thirties want to know. They want to read your articles on 'how to have a mind-blowing orgasm' or 'how to lose weight without dieting'. They don't want to read Elena Gilbert's 'how to save the world'," the editor sighed, shaking her head in disdain.

"Mrs Lockwood, I really think it would make a difference," Elena stated, persuasion and passion laced in her voice.

"I have a proposition for you then," Carol grinned, snaking her hands together like a criminal mastermind. "If you can make a difference in the sales with this next 'how to' article then I will let you write any mumbo jumbo that you want."

"What's the article?" Elena questioned warily.

"How to change a womaniser into a one woman man," Carol grinned, motioning the title with her hands. "You'll have ten days to make a commitment-phobe into a monogamous man."

"What?" Elena sputtered nervously. "Who's the guy?"

"None other than Damon Salvatore," Carol smirked, arching her eyebrow as she waited for the brunette's reaction.

"Damon Salvatore, the renowned businessman of Saltzman Advertising who has a woman in his bed practically every night? I'm supposed to make him into a one woman man?" Elena questioned, her voice shaking with worry. "T-That's impossible!"

"Well, Elena, you can take it or leave it," Carol responded, fixing her with a glare. "But, if you do in fact decide to leave it then you can leave the office while you're at it. For good."

Elena shook her head as she looked at the woman who was trying to ruin her life. She bit her lip as she tried to keep the tears that stung her eyes from falling. "I'll do it," Elena whispered before inhaling a strangled breath.

"Good, I'll expect a detailed report on your tactics and their results on my desk on Thursday morning." Carol quickly collected her magazine mock-up and stood from the desk so that she looked down on them all. "That's all then. Remember, do your jobs correctly and there will be no problems."

Elena clenched her teeth together in anger as Carol's pointy heels clicked along the floor until she exited the room. Caroline saw how her friend was on the brink of falling apart and quickly pulled her from her seat. Elena felt as she was guided along the hallway by someone holding gently onto her arm. Her other hand came to her face in the pretence of fixing her hair but in fact she was hiding the tears that were falling from her doe eyes from her fellow employers.

"Oh, sweetie," Caroline exclaimed as she pulled Elena into a tight hug when they finally reached the woman's bathroom.

"Why d-did she have t-to choose today of-f all days?" Elena whimpered as she clung to the navy satin of her friend's blazer. She buried her head into Caroline's neck, allowing herself to be lost in the blonde curls and strawberry scent that was Caroline Forbes.

"I know. Shh," Caroline soothed as another bout of sobs wracked through Elena's body. "She's an awful woman."

"You got that right." Elena let out a watery chuckle as she pulled out of the blonde's embrace. "I mean, just because I ended things with Tyler in high school, she feels the need to punish me for it. I think that the only reason she hired me was so she could torture me with all of these ridiculous stories."

"She is extra hard on you," Caroline sympathised.

"I know! She wants my article on her desk on Thursday when everyone else can bring them in on Saturday. She's just waiting for me to screw up so that she can fire me," Elena cried, her voice rising in righteous anger with each word.

"Sweetie, why don't you quit?" Caroline questioned, hating how upset her friend was because of their bitch of a boss.

"I can't," Elena growled. "It was hard enough to get this job in the first place and I want to accomplish something here. I don't want the last two years I worked my ass off to be for nothing. Even a reference for another job would be a bonus; I just have to hold out until another job opens up. I heard that Bill Davies is retiring from the New York post in the next few days so, I'm going to apply there."

"Good for you," the blonde beamed. "If you get that job, then you can write about anything you want to and that bitch, Lockwood, won't be able to do anything about it."

"I know why she's so awful to me but she's always in a foul mood anyway. I mean, what's her problem?" Elena grumbled as she stared into her friends blue eyes.

"Maybe she's not getting any!" Caroline snorted at Elena's hysterical laughter. "It's true, Mr Lockwood would probably get his dick frozen off if he went anywhere near that ice queen."

"True!" Elena giggled before looking in the mirror and her expression soon turned to one of sadness as a tear trickled down her cheek. "God, look at my make-up."

Caroline looked at the brunette and couldn't help the small smile that spread across her face. Even in despair, Elena always had to have a put together appearance so that no one thought she was weak.

"Hey, we can sort that out in a minute," Caroline protested as she pulled the concealer from the other woman's tight grasp. "Now, talk."

"I should have moved on by now," Elena whimpered, shaking her head to dispel the tears. "It's been five years."

"Honey, your parents died. That will always affect you," Caroline smiled sympathetically. "Is that why you were late?"

"Yes, I went to their graves to lay down flowers. I sat there and talked to them and I guess I lost track of time," the brunette explained as Caroline rubbed her arm in comfort.

"That's totally understandable. Do you want to stay in and chat tonight?"

"No," Elena sighed in disappointment. "I have to get started on this assignment. How am I going to even attract Damon Salvatore?"

"Seriously?" Caroline scoffed. "You're hot! He'll be on you like a fly on shit."

"Nice, Caroline. Real nice," Elena laughed, shaking her head at her friend's words.

"It's true! I mean look at you," Caroline exclaimed, turning Elena to face the mirror as she began to repair her friend's make-up. "If I was a guy, hell if I was a lesbian, I would totally tap that."

"Really?" Elena murmured as a red tint formed on her cheeks.

"You are beautiful, Elena Gilbert. Come on, say it," Caroline cajoled as she stood behind the brunette, her hands on Elena's shoulders.

"Caroline, no," Elena laughed, trying to escape the blonde's hold.

"I'm not letting you leave until you do. So, repeat after me." Caroline cleared her throat. "I'm Elena Gilbert."

Elena sighed. "I'm Elena Gilbert."

"I am a beautiful, strong woman." Caroline nudged Elena when she hesitated.

"I am a beautiful, strong woman."

"Who is going to rock Damon Salvatore's world tonight and ruin him for the rest of woman kind."

"Caroline!" Elena exclaimed in indignation. "I'm not going to have sex with him tonight."

"Oh, I know. I just meant that you will rock his world with your presence," Caroline smirked, winking at her friend in the mirror. "Although, it's nice to know that you think you could rock his world with sex. Maybe I should rethink the whole tapping thing. Yes, I'd tap you if- You know what, I'll just tap you if you're ever up for it."

"Caroline!" Elena laughed at the blonde's rambling.

"Don't you 'Caroline' me. I've seen you with a few tequilas in you; I think I could persuade you," Caroline winked.

"I think I should tell Matt about your lesbian tendencies."

"Oh, he knows," Caroline wiggled her eyebrows. "And, for your information, if you ever want to participate in a threesome then Matt and I are totally up for it."

"Thanks for the offer but I think I'm all right," Elena smiled at her friend and her ingenious ways at making her feel better.

"Okay, back on topic. Repeat. I'm going to rock Damon Salvatore's world tonight and ruin him for all woman kind."

"I'm going to rock Damon Salvatore's world tonight and ruin him for all woman kind." Elena exclaimed as confidence radiated through her.

"You got that right!" Caroline agreed with a grin. Her grin soon fell from her face as Elena's changed to a grimace. "What's wrong?"

"What am I going to wear?" she questioned with wide, brown eyes.

"Oh, I have the perfect thing. Come up to the swag room and I'll sort you out with a heart-stopping, jaw-dropping outfit," Caroline smiled as she clapped her hands together with glee.

"Does that mean I get the Caroline Forbes makeover?"

"You got that right! I will see you at five o'clock sharp. Don't be late," the blonde warned, wagging her finger. Elena smiled in agreement as she made her way towards her desk. With a quick bid of goodbye to Caroline at the elevator, Elena set to work on what was going to be her best article yet.

Two hours later and Elena had been searching furiously through the internet to find both the best turn ons for a man and the worst turn offs. She had gathered lots of useful information and was sure she would put it into practice tonight. She had begun to jot down the most important ones in her ever present notepad when her office phone began to ring.

"Hello, this is Elena Gilbert from Dazzle magazine. How may I help you?" she drawled out as she balanced the phone between her ear and shoulder.

"Hi 'Lena!" a masculine voice exclaimed down the line.

"Jer! How are you?" Elena questioned warily.

"'Lena, you have to stop worrying about me. I'm not going down that road again," Jeremy responded immediately, conviction oozing from every word.

"I know," she sighed, rubbing her eyes with her delicate fingers. "I just don't want you to get involved with drugs again, Jer. I worry about you."

"Well, don't. Really there's no need. I have Bonnie now and the baby on the way, I wouldn't risk that. How's my little sister doing?" he questioned, worry in his voice.

"I've been better. Work is a bit of a drag," Elena grumbled.

"Anyone I need to beat up?"

"No," she laughed. "Put away the over protective brother act for another day. It's just this article I have to write."

"I've read some of your work and I'm not sure I want to know," Jeremy shuddered, remembering the article his baby sister had written on orgasms.

"Jer, you know I'm not a virgin so stop pretending that I am!" Elena grinned as he grunted disgustedly.

"Lalala! I can't hear you!" he chuckled.

"Jer, I actually need your help." Elena explained, fiddling with her hair nervously. "Do you, by any chance, know where Damon Salvatore goes out at night?"

"There's one club he usually goes to with his friend, Alaric Saltzman. Why?" Jeremy speculated.

"He's the subject of my article," Elena explained hastily, not wanting to offer any more information than that. "What's the name of the club?"

"It's called Sundown. I only know because he kept dragging Alaric there whenever I was doing artwork for their advertising company. He's a first rate jackass, Elena. I'd choose another subject," Jeremy grimaced, knowing exactly what a man like Damon Salvatore would want to do to his sister.

"I can't, Jer. Thank you but I should probably be getting back to work. Can we meet up for dinner tomorrow night and reminisce?" Elena sighed as the memories of their parents flooded her mind.

"Sure thing, sis. Love you."

"Love you, too," Elena sighed with relief as she put the phone down.

As her mind drifted, she smiled; she had some tactics ready, a makeover with Caroline planned and her destination was established. All she had to do was find Damon Salvatore and blow his mind and that was exactly what she would do.

Reviews are, as always, greatly appreciated! Remember to PM if you're interested in being a pre-reader! Amy xo

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