Hey! This is my first time trying to write a fanfiction so please leave any tips and feel free to point out problems/errors. I hope you like it!

Chapter one

Elena carefully laid out her outfit for the blind date Jenna has set her up for tonight and went into the bathroom to get ready. She began by straightening her hair then curling it at the end to create more volume and edge to her look, she then began to apply little make up to her face just enough to bring out her eyes and added a pinkish purple color to her lips to match the dress she had picked for her evening. She walked back to where she carefully laid out her outfit and began to dress and accessorize, Elena looked at the clock and saw that her date should be arriving soon and took one last look in the mirror and admired the work. Elena was dressed in a tight purple dress, which had a geometric print in grey. She wore grey pumps, and accessorized by adding many bracelets and bangles to her arms and had stud diamond earrings on. Elena nodded once at her reflection, grabbed her purse and headed to the living room to wait for her date

Elena looked at the time again, thirty minutes have passed and there was still no sign of her date. Has she been stood up? Elena sighed as she felt herself begin to drift to sleep but was startled awake by the sound of a knock coming from her apartment door. Elena immediately stood up and began to smooth her dress down, running a few fingers through her hair. She plastered a smile on her face and headed to answer the door. What Elena did not expect was to be welcomed with the bluest eyes she has ever seen in her life "Sorry if I was a little late" the man, no sorry, the incredibly good looking man in front of her said as he smirked at Elena. "Oh no worries you only have me extra time, you know thirty minutes late it's nothing really. I'm Elena, Elena Gilbert" Elena extended her hand out to him and he took it "Damon Salvatore" he grinned "So should we get going?" Damon looked at her and made a beckoning motion for her to step out.

Elena stepped out and they both began walking to the road, she decided to begin small talk to try and clear the awkwardness between the two "How long have you known Alaric for?" she asked and looked at Damon looking at his figure rather than solely staring into his blue eyes, Damon was a very attractive man but dressed rather inappropriately for a date. He had a baseball hat on with a couple of raven black tousled hairs peaking from underneath, dressed in a leather jacket and jeans. Elena suddenly felt overdressed. "High school" He replied. "Ohh that's great" she smiled and him and looked around "So where's your car?" "Right here" She looked back and saw Damon handing her a helmet and to his side was a black motorcycle "You know you can hold tight if you want to, I won't look into it or anything" He winked, oh no, she was not going to do this "ohhh no, um I don't think that would be the best option and all since you know I'm wearing a dress and heels and all" She pointed at herself as to make a point and Damon's arm holding the helmet began to fall back to his side "But you know! We can just take my car and it's new so I love driving it and this won't be a problem at all" Elena began to fish for her car keys from her purse and pointed at the smart car she had parked right in front of her house. Damon's face fell for a moment before he plastered a strained smile "Sure" He said as he put the helmet back on his bike and began to walk towards Elena's car.

Elena smiled back and they both got into a car, "So where'd you make reservations at?" she turned to look at him as she started her car, "uhh, reservations? Umm yeah" Damon looked at her apologetically and began to rub the back of his neck "You didn't make reservations? Oh um it's cool uhh" She looked at him and felt herself get flustered. He just smirked and held his hands up in front of him "So where shall we go?" he asked and Elena felt a bit of anger spike up but quickly began to calm herself "You know I know this little café my friends and I used to always go to, we can just-" Elena's blabbing was cut off by a ringtone sounding off, coming from Damon's pocket. "Go on" He encouraged her, but she just stared at him "Aren't you going to answer that?" she asked "nooo, go ahead I'm sure it's nothing serious" he smirked at her and gave her a hand motion to continue. Elena held her annoyance and tried to continue explaining but ended up losing her nerve "Can you please just answer your phone? Its fine really, just answer it" She encouraged him, trying not to roll her eyes, busying herself by looking at her perfectly manicured nails as he answered her phone "Hey-y you, aha you know me I'm just doing stuff…Yeah sure, mhm, you know what? Why don't we make that 10:30 instead.. mhmm ok bye see you later" Elena turned to Damon disbelievingly, "Yeahh, sorry it's a…um..sick friend" He smiled at her. "You know" Elena drawled, "We don't have to do this" Damon looked at her "Really?" His eyes widened "Okay then" he began to open the car door to step out. "Oh my God, are you serious" Elena looked at Damon as he sighed and leaned back in the car and said "Okay, let's be honest here, you obviously don't like me". Elena sighed and explained "but at least since people close to us set us up then I think we should owe it to them to at least try this out" She was on her last nerve now and was very close to exploding from anger "We owe them to fake smiles and small talk? I mean come on the best scenario for the both of us is if we both get a little drunk and we hook up" he explained, completely casual. That was it, Elena was going to explode, 1, 2- oh screw it, she thought "What kind of an asshole are you?!" Elena shouted, "Oh come on it's a Saturday night I want to have some fun" Damon tried to explain "I just want to go see my um.. sick friend.. and you can do whatever you usually do on a Saturday night, you look like you read.. You know you can just go read a book.. Do you blog?" That was it for Elena "DO I BLOG?" She hit the steering wheel of her car, "OKAY, you want to ensure that tonight won't be a lousy night? HERE'S A TIP, Don't show up half an hour late, and DON'T MAKE A BOOTY CALL INFRONT OF ME", "Oh come on she's sick", "OH, were you going to heal her with your magic Penis?", "Okay, fine, you want to go out.. Let's go out" he sighed, she could not believe the ego on this man "Oh no I'm not going out with you NOW, what are you CRAZY?" She switched off her car and began to get out of it "GET OUT OF MY CAR! GET OUT OF MY SMART CAR! I don't know what Alaric and Jenna were thinking!" she shouted at Damon as she walked out back to her house. "Yeah me neither" He said.

Elena brought out her phone and dialed Jenna's number "Jenna, the only way you can make this up to me is to promise that I will never have to see this man ever again in my life"

Thank you for reading! I promise to post the next chapter as soon as possible, please review and tell me what you think.