So happy with the amount of reviews I got on just my first chapter, it might not seem a lot to you guys but to me it was amazing. Anyway, I hope you like this chapter about Damon's attempts to woe Elena, sticking to one of your reviews (and my intentional thought) Elena will not be so easy persuaded to sleep with Damon, he's gonna really have to work for it! Hope you enjoy! - Jess.

All day that following Monday at school Elena felt eyes shadowing her every movement. When she was walking into school, when she was getting books from her locker, when she was eating her food in the cafeteria. The problem for Elena was she had no idea why or who was watching her, she just knew that someone was.

The answer quickly revealed itself on her way to maths class in fifth session class.

"Elena?" an unfamiliar voice called from a distance, she was confused, yes she was the only Elena in the full school but nobody ever willingly spoke to her. She was a freak, a nerd, a loser, no she must have misheard whoever was calling her, surely they were shouting on someone else. Not her, maybe an Ellen or a Helena but not Elena. Realising that it was probably her ears playing up, Elena walked on into the maths classroom and took her place in the squeaky chair at the front of it. As she was opening her text books at the page they were studying she felt a dark figure looming over. Looking up she found herself mesmerised by the two crystal blue pair of eyes fixated on her, searching her own eyes - shielded by glasses - as if they could see into her soul. Why was Damon Salvatore standing at her desk?

Mentally shaking herself out of the trance she had found herself in Elena gave Damon a questioning look.

"Can I help you with something?" she asked, suspiciously.

"I've been meaning to ask you something." Damon smiled at her, his eyes flaring up with an emotion Elena didn't quite catch.

"What?" she said, what the hell would Damon fucking Salvatore, the hottest guy in school and possible Mystic Falls and the surrounding areas - and the biggest jackass as well - want to ask her? Elena swallowed nervously.

"Yeah, um," he seemed to be stalling, as if he was scared of her answer yet at the same time he still seemed his usual cocky self. "I was wondering if, if-"

"Right class, please take your seats, I will be round in a second to pick up your assignment, make sure you have it ready to be collected." the stern voice of Mrs McKay cut off whatever Damon was going to say.

"If," he tried to continue.

"Damon. Seat. Now." The teacher called.

Damn it! Elena mentally groaned, what did he want to ask her? For a minute Elena felt like punching her second favourite teacher in the school as Damon gave her an apologetic smile and made his way to the back of the classroom.

"Elena," a soft probing in her back from someone's finger midway through the maths lesson caused her to flinch. She turned around to the boy behind her.

"What?" she asked surprised that he was speaking to her, he never had before. What, was this just a day for random people speaking to her? What was everyone's deal?

"This is for you." He discreetly passed her a note with her name printed on it, carefully she took it and opened it, warily as if it might explode or something.

"Want 2 go out after skl, the grill?

- D x"

D? As in Damon? As in Damon fucking Salvatore? Why on earth did he want to go out with HER? That must have been what he wanted to ask her. Why but? Why a sudden interest now when Elena was positive that 48 hours ago he had no idea she even existed. It must be some sort of joke, yeah, a laugh to his friends, she'd say yeah then he'd laugh and say he was kidding, humiliating Elena. Even if it wasn't a joke there was no chance in hell Elena was going out with Damon, nope never. For one she couldn't go anyway, not to the grill at least, Caroline and Bonnie would be there, pissed that she'd being blowing them off for the past two weeks and secondly, she really didn't want to. Damon Salvatore was a notorious ladies man, a player; he treated girls like play things just because he could. Anyway, Caroline and Bonnie would be furious at her if she turned up with a boy - after saying she was so busy with homework.

"No." she scrawled across the paper before handing it back to the boy behind her to pass back.

Throughout the lesson she was probed with several more notes which she ignored only to the infuriation of Damon who groaned every time he watched her through the notes in the nearby bin without even reading them. Elena didn't care, as hot as Damon was, he was also the world's most arrogant dick who hid his amazing ability at maths - for she had noticed, as Mrs McKay looked for her test results in the pile of student results, that Damon's marks were always rather high - just so to not damage his reputation. In Elena's books, that screamed pathetic. He thought he could get any girl he wanted but no, he couldn't get Elena, he would never get Elena, she'd never stoop to that level. And whatever game he was to playing with her, asking her out, she wasn't for it, she refused to become another one of Damon Salvatore's infamous conquests, talked about like a piece of meat, compared on a scale of "who was better, her or her?"

When the bell rang at the end of the lesson Elena quickly gathered up her books and charged out the classroom at lightening speed, unusual for her as she was usually the last to leave. She ignored the call of her name behind her and the footsteps shading her quick pace as she tried to make her way to Chemistry in peace.

"ELENA!" Damon called again, exasperated.

Finally, after a moments hesitation Elena stopped walking and turned her head a fraction "What do you want Damon?"

"You." he grinned cockily, seeing the expression of shock on her face he rephrased his question "As a tutor, I need help in maths."

Elena was gob smacked; he'd went from a date to tutoring in just one lesson? This must be his second tactic. Elena rolled her eyes at the thought.

"I saw your last test results Damon, I think you're doing just fine on your own."

She went to walk on but Damon captured her arm and positioned himself in front of her "I was thinking more like a study date?" he raised his eyebrows.

Elena studied him intensely, trying to figure out what his game was, Damon shifted uncomfortably before her eyes.

"Sorry." she finally said before pushing past him "I'm busy."

"But I didn't tell you a day or time." Damon called, watching her walk away from him.

"I'm busy every day, all the time." Elena answered.

Damon frowned to himself, never before had any girl rejected him from anything, not a dance nor a dinner and not even something as simple as a ride home from school. In fact most girls went out of their way to make themselves available for Damon but Elena was clearly no ordinary girl. He smirked to himself, Elena Gilbert was a tough nut to crack and oh, as if Damon didn't love a good challenge.

"Elena Gilbert to the head teacher's office, now." an oh-so-familiar voice ordered as she scribbled down different types of alloys in chemistry.

Her head shot up "What for?" she glared at Damon suspiciously.

"Do you have a note, son?" Elena's chemistry teacher questioned.

"Sorry no, Mrs Burns just said it was urgent and to get Elena immediately."

"Urgent? Well you best be going, Elena. Quickly, don't keep the head waiting."

Elena sighed and stood up before brushing past Damon to get out. They both walked along towards the office in an awkward silence.

"Why would the head teacher want to see me Damon?"

"She doesn't," he grinned cockily "but I do."

Elena stopped walking and turned to face him "You mean to tell me that Mrs Burns DOESN'T want to see me and you dragged me out of class on an urgent message for no reason?"

"Yep."

"You're a joke, Damon Salvatore." Elena scolded before turning to head back to class. A strong arm caught her and held her in place.

"I just wanted to see you, 'Lena."

"DON'T call me that and just LEAVE ME ALONE!" Elena cried, exasperated. "Listen I don't know what your game is but leave me out of it!"

Damon opened his mouth to respond before he could even say one word he was cut off by a stern voice.

"Do either of you have a note for being out of class?" A teacher that Elena wasn't familiar with frowned at them whilst he looked at the position they were in. Elena half-turned away, fury in her eyes, Damon latched onto her arm looking apologetic. The perfect scene of a lovers tiff. Elena groaned internally at the thought.

"No sir" Elena replied weakly.

"And do you, Mr Salvatore?"

"Afraid not."

"Do you have a valid reason for walking around the school during class hours?"

Both Damon and I shook our heads.

"And what is your actual reason for being out here?"

"Just needed a walk, sir." Damon smirked, a cocky grin plastered across his face. The teacher glared at him.

"Well I expect you and your little friend to take a walk BACK to class immediately and I will see you both in detention after school." he looked them both up and down. Elena nodded and then gulped; she turned on her heels and speed walked back to class as fast she could. Detention? Elena Gilbert was a straight-A student, she got endeavour awards presented to her every year, she was the good girl, and she didn't get detention, that wasn't her. She put her head in her hands, this was his fault, Damon Salvatore, he had did this.

"You're late." A male voice barked at Elena as she scuttled through the door.

"Sorry," Elena replied sheepishly. "I've never been here before; I didn't know where to go."

"That is not a valid reason, now go and find a seat and begin copying out this textbook." The teacher, Mr Gillespie - who had been nicknamed "Mr G the baldy B" by his students - threw a rather thick text book at her which Elena swiftly caught before heading to the nearest possible seat. The class wasn't what Elena would call "full" but there wasn't many leftover seats in there, it was full of adolescents whispering quietly amongst themselves and throwing her strange looks for WHY was the class suck-up Elena Gilbert in detention? Elena rolled her eyes, she had no idea either. Countering her previous thought, it didn't matter how many seats were left in the room, that didn't give the next late student the right to saunter into the classroom and take the available one next to her.

"Go find another seat, Damon" Elena hissed. "This is your fault I'm here in the first place and I'd appreciate it if you let me be."

"I know," Damon replied meekly "and that's why I'm sitting here, I wanted to apologise for my actions, I guess I was just upset that you said no both time I asked you out and felt rejected."

Elena was gob smacked. The infamous Damon Salvatore was apologising to her with only sincerity ringing in his voice, was this for real?

"Um, ok. Thanks." Elena muttered back.

"Now," Damon titled his head to the side cockily "about that study date..."

Instantly Elena was wary again. How could this boy go from sincere to cocky in just a few seconds? There must be a reason this boy was pestering her so much, why was he so desperate for a study "date?" Elena didn't think he was that concerned with his education.

"Forget it, Damon. I told you I'm busy."

"Please, just hear me-"

"SALVATORE, GILBERT WILL BOTH OF YOU STOP TALKING" The stern voice of the moody teacher at the front of the classroom bellowed.

"Sorry, sir." Elena whispered, lowering her head back to the sheet of paper, which had barely been written on, on her desk and tried to continue copying out of the textbook discreetly.

"Have either of you actually written anything so far?" Mr Gillespie stormed up to their adjoining desks in the third row of the classroom.

"Nope." Damon glared at the teacher looming over his desk.

He lowered his head until he was inches of Damon's face, it must have been intimidating but Damon didn't bat an eyelid, not even when he begun screeching at him.

"And why not, BOY?"

"Because I don't have a pen." Damon rolled his eyes.

"And what about your friend here, has SHE not got a pen?" Elena slithered back in my seat as far as she could go as the teacher turned his attention on her.

"Well?" he barked.

"Um, I don't, I don't know." She stuttered.

"What do you mean you DON'T KNOW? You either have a pen or you don't, which is it?"

Elena's hands were shaking as she tried to retrieve her bag from the side of her desk but she was so nervous she ended up dropping it and the contents of it scattered every where. Everyone in the room, who was fixated of the confrontation between the furious teacher, Damon and herself, begun laughing with the exception of Mr Gillespie who's ears were so red, Elena was surprised smoke wasn't coming out of them. The humiliation was dreadful.

"You can't even do ONE simple task you stupid, intolerable little girl!" the teacher roared as Elena dropped to her knees and begun picking up the spillage from her bag.

"Hey, don't fucking talk to her like that" Damon shouted back to him, leaning down to help her.

Mr Gillespie blinked and stared at Damon for what seemed like a long time as if he simply could not comprehend what had just happened. Finally, an indescribable anger crept into his features.

"I'll report you for that boy, that language is not tolerated in this class! You'll be out of this school before you can even blink!" The teacher fumed.

"And you think calling her stupid and intolerable is acceptable?" Damon glared, pulling Elena to her feet but not letting go off her hand. "You report me and I have a class full of witnesses who can confirm that you bullied a student, I think you're the one that'll be out of school before you can blink, c'mon Elena."

And with that, Damon begun to lead Elena out the classroom but not before she pulled her hand away from his, who did Damon think he was, her knight in shining armour? Elena Gilbert could take care of herself thank you very much.

"I can't stand that fucking cunt." Damon ranted as they made their way out of the school building, Elena still looking over her shoulder every few seconds, scared the furious teacher was going to come charging after them.

"Don't worry he won't come" Damon laughed noticing her uneasiness. "And you won't get into any trouble, Gillespie's like all bullies, once he's put in his place he just goes running scared."

Elena just nodded her head, completely uninterested in the conversation and more interested in getting the hell away from school and - more importantly - Damon.

"So..." Damon drawled, looking at her with desperate eyes as he struggled to find a conversation starter.

Elena smiled; a weak small half smile was the best she could muster. "Thanks for sticking up for me in there Damon but in the future I'd rather you didn't bother, I can take care of myself. Now, I must go I'm late home."

Damon stood dumbstruck and open mouthed for at least a minute whilst she scampered away. He had been positive that if he'd did what he'd just did, defend her honour in front of a class room of his peers, she would have went running into his arms, eternally grateful. But no, if anything she seemed angry that he'd defended her, Damon got the feeling that he'd damaged her pride. He was quickly figuring out that Elena wasn't the kind of girl that liked to be protected... but what kind of girl was she? Intelligent, yes and mysterious, seemingly immune to his charm - a first for Damon - and she seemed strong-willed, realistic, lonely? Damon Salvatore was a very determined person and at this point he was determined - even more determined that when he'd first made the fucking bet - to figure out whom exactly Elena Gilbert was.

Running out to his car Damon started it up and quickly sped out of the school parking lot to catch up with Elena, walking at a fast pace away from the school, on the sidewalk.

"Need a ride?" he called, lowering the window on the passenger seat and smirking at her.

"No thanks, my house is just along here." she replied firmly, breaking into almost a light jog, her school bag bouncing on her hip.

"Oh come on, it'll get you there quicker. I owe you for getting you detention in the first place, c'mon, hop in!"

"Why would I hope in when my home is on the other side of this lane?" Now she was smirking at she pointed towards a lane strictly for pedestrians. Running towards it she was sure to yell over her shoulder "Goodbye Damon."

Damon sighed and drove away, he had just been rejected for the third time in one day and he was out of ideas for how to woe Elena. This wasn't even about the bet anymore, though Damon could imagine the humour on Tyler's face if he found out how many times Elena had rejected him. Luckily he had been absent today and had missed Elena throwing his notes to her in the bin. Right now, however Damon couldn't care less about Tyler or his reputation or anything really, all Damon cared about was Elena. He wanted to know why she was so distant with him and everyone else; she never seemed to let anyone in, why she seemed sad all the time and why she never seemed to be interested in her friends' conversations at lunch, why she looked like she was always deep in thought. These were all questions that he needed to know the answers to, he didn't even know why, he just had to know.

Damon drove home with a smile on his face, an idea had finally struck him and he knew exactly how he was going to obtain those answers. Punching a number into his phone Damon held it to his ear. "Hello, Sage."

Introducing Sage, yes or no? Don't worry, she won't be a main character she's just there to do Damon's dirty work next chapter! Also, do you want me to develop more minor characters e.g. Caroline/Tyler/Klaus (do you even want to meet Klaus?) and see more of Stefan/Katherine's relationship or Jeremy/Vicki's? Review and let me know!