DISCLAIMER: I do not own anything from The Vampire Diaries.

Hi everyone! This is my first ever fanfiction but I am so excited to be writing it. I've been reading Delena fanfiction for probably a year now and I never thought I was talented enough to write my own. Soon enough I had run out of fanfictions to read so I thought i'd try my own. In my fanfiction everyone is human so no vampires, werewolves doppelgangers etc. Please if you have any constructive criticism or any ideas for the plot etc please don't hesitate to message me, i'd love to hear your opinions etc, anyways I hope you enjoy!

Elena Gilbert lost her parents in a car crash in the summer. Damon Salvatore is involved with many different crimes. Two People who are popular in different ways. Elena's boyfriend Stefan is doing everything he can to save their relationship but what happens when older bad boy brother Damon becomes Elena's friend?

Elena's POV

I woke up Monday morning and realised today was the day i had dreaded the most. My first day back at school since my parents had died. I'll have to smile and say "I'm okay thanks." when someone asks how I am. Deep down I know that I am not okay. My Aunt Jenna has been doing a great job of taking care of Jeremy and I but I miss my parents every single day.

I heard a loud buzzing noise before realising somebody was calling me. I picked up my phone from my table and looked at the Caller ID, to see it was Stefan my boyfriend. He had been so good to me over the past couple months but i've just felt like we've lost our spark that we once had. I still love him of course but i don't think i'm in love with him. I've brought it up a couple times but he thinks i just need time to come to terms with my parents death but i've felt this way a couple weeks before my parents death. So because he wouldn't let me talk to him about our relationship i'd been avoiding him for weeks but i knew i'd have to face him at school today.

"Hello?" I said my stomach filled with nerves because there are so many things we need to talk about.

"Hey Lena, I was just calling to let you know i wouldn't be able to walk you to school today."

I was surprised that he was pretending that there was nothing going on between us and that I hadn't been avoiding him for a month.

"Oh right, is everything okay?"

"Well Damon's back from his little trip and my Dad said that he has to drive me to school."

I had only spoken to Damon a couple of times when I was with Stefan. There were rumors that he was working for the Mikaelson family which were heavily involved with many different crimes. Damon had been arrested in the first week of summer on suspicion of drug possession and drug trafficking but he was released as they had no real evidence against him. He then disappeared for the rest of the summer. All I really know about him is that he doesn't live with Stefan and his Father but he has to have dinner every Friday with them.

"That's alright i'll just see you in class."

"Okay, I love you." My heart stopped beating for a moment when he said those words and I wasn't sure how to reply.

"Yeah, um bye." I said stupidly which was bound to bring on a serious talk which we needed to have.

Damon's POV

I hopped into the driver's seat of my camaro while a grumpy Stefan got into the passenger seat.

I looked over to see Stefan with a frustrated look on his face.

"C'mon Stef spill what's on your mind." I said and jokingly punched him in the arm. The only response I got was a huff mixed with a sigh.

I let out a dry laugh. "Ah I get it now, you have girl problems."

Stefan glared at me which told me I was spot on.

"Are you still with that hot Elena chick?" I asked knowing i'd piss him off.

I never knew too much about Elena just that she was Stefan's girlfriend. The only time i'd see her was in school or if she was at the house to see Stefan. She has the same features as Katherine but from what i've gathered she is nothing like her. Katherine was manipulative and selfish, Elena didn't seem anything like that.

"Yes I'm still with her." He snapped at me.

"Okay so what's the problem?" I said as I started to drive to school.

"Nothing i'm fine I just wanted to walk her to school but Dad is making me go with you"

I knew that wasn't the only reason he was in a bad mood but I let it slide. We pulled up to Mystic Falls high school and I saw Elena walking and laughing with her friends Caroline and Bonnie. She was so cute when she laughed. I quickly stopped myself for thinking that way. I spotted my best friend Klaus Mikaelson with his brother Kol. I parked my car and Stefan got out as quick as he could and ran to Elena.

"Mikaelsons!" I shouted across the car park to get Klaus and Kol's attention

"Ah Salvatore, it's good to see you" Klaus greeted me with a smirk as I walked up to stand outside the school with them.

"I'm alright, where's your sister?"

Rebekah is a junior and we hooked up a few times but i knew how much I was pissing off Klaus so I cut it off not only to clear things with Klaus but that girl can be a bit intense.

"I'm going to ignore that you just said that. Are you free to meet us at the warehouse tomorrow at 8?"

"Yeah i'll be there." I replied before walking through the doors for my first day as a senior.

Elena's POV

Caroline and Bonnie gave me a worried look and before I could question it Stefan appeared in front of me.

"Hi." Stefan said shyly.

"Bonnie I have your um.. English book in my locker!" Caroline said trying to not make it obvious she was trying to leave us alone. They both knew how I felt about Stefan even though Caroline was trying to convince me I was wrong. They quickly hurried towards Caroline's locker leaving Stefan and I alone.

"Look I know you're feeling like we don't have that spark that we once had but I love you Elena and I want to try and get our relationship back to what it once was." He said putting everything out there.

"Stef I ju-" before I could say anything he cut me off.

"Elena please come over after school and we can talk about everything please just give me that." he practically begged.

"Okay." I agreed.

Now that he was standing in front of me I realised I hadn't thought this through as much as I thought. I want to try make things better because I love him and I realise that now.

I leaned in and kissed him on the lips quickly to show him I was really going to give him a chance.

"Walk me to my locker?"

"Sure" he said and I grabbed his hand before walking into the school.

After a long day at school it was finally time to meet up with Stefan and go back to his house. I spotted Stefan outside the school talking to Damon.

"Elena!" Stefan greeted me.

"Hi Stef. Hello Damon." I said ignoring the feeling I got as I said Damon's name.

"Elena. Hey Stef i'm gonna go see you in the morning." Damon said and patted Stefan on the shoulder and walked away.

"Look Elena, I am so sorry but my Dad wants me to attend some business meeting he says they appreciate family and since Damon doesn't have the best reputation he asked if I could."

"No it's fine you go we can talk tomorrow okay?"

"Okay." He pulled me into a quick kiss and then we said our goodbyes.

I decided to walk home alone so I could think without Caroline talking in my ear. I decided I wanted to go to a bar and have a couple drinks alone.

I walked home had some food and headed out before Jenna could stop me. It's a school night and I don't want to lose her trust. I walked down to my local bar and sat down and ordered my first drink.

Damon's POV

The first day of school was hard with everyone talking about me getting arrested. I was let go free of any charges and everyone knows that. I walked into my favourite bar and took my usual seat. I ordered a glass of bourbon and look a large sip trying not to think about the time I spent in jail. It still haunted me and I definitely do not want to end up there again, it was hard even for 2 weeks if it was any longer I don't think i'd be able to handle it. I turned to my left and I saw a girl with dark hair which was covering her face, looking down at her glass deep in thoughts. When she lifted her head I realised it was Elena Gilbert.

"Elena Gilbert, underage and drinking in a bar." I said with a smirk.

She looked at me scared and her face softened in relief as she realised who I was.

"Don't rat me out?" she pleaded.

"It's not like I didn't do it when I was underage so i'll let it slide. Though, can I say anything to my baby bro or does he not know?"

"No he doesn't know and i'd like to keep it that way."

"My lips are sealed." Elena flashed a smile before staring back at her drink. I saw it was empty and I wasn't sure if it was appropriate to buy her a drink. I decided I would. I waved at the bartender to get her attention and she slid over as fast as she could.

"What can I get for you handsome?" I could see Elena rolling her eyes and I laughed to myself.

"I'll have another bourbon and get another drink for this lady." I motioned to Elena and the bartenders face dropped and she walked away to make our drinks.

"Damon you don't have to I have my own money."

"With a girl as pretty as you looking as sad as that I thought you deserved a few free drinks." she flashed a grateful smile and looked at me straight in the eyes for the first time. We sat and stared into each others eyes for a moment I felt myself getting lost in her dark pools. The bartender interrupted our little stare and handed us our drinks.

"So what has got you so down Gilbert." I know I have never really talked to her but I felt so comfortable that I decided to not end our conversation there.

Elena's POV

It was weird being sat at a bar with the older Salvatore brother but I felt happy.

"I'm not sure if I should answer that, we don't really know each other and i'd rather not overwhelm you with my crazy life."

"Trust me my life is probably a thousand times more crazy and hectic than anybody else's." he said and laughed. God he is so gorgeous. His icy blue eyes glowing through the darkness of the bar almost made me forget what we were talking about.

"Okay then, I am in a relationship i'm not sure I even want to be in, yet everyone is telling me that we are perfect for each other and I just don't feel it. My parents are dead and i've no idea how i'm supposed to get through this. I have to pretend to be strong for my brother even though on the inside i'm crumbling apart. My Aunt Jenna is trying so hard to do everything in our house but it's just not the same without them and now i'm sat here in a bar drinking with my boyfriends older brother who I barely know and telling secrets I haven't even told my best friends." I didn't even realise the tears that were freely flowing down my face. I just unloaded so many thoughts that were on my head and it felt like it was a weight lifted off my shoulders to finally talk to someone.

"Elena I know exactly what you're going through. When I lost my Mother my Father blamed me for it. I was the one who found her dead in our living room. He said I was too much trouble and it leaded her to take one too many pills. But what he didn't tell me was she was a recovering drug addict. She had been clean for 2 months and then she was straight back on them. Many times I walked in on my father screaming and punching her. It was terrifying to see that. So after her funeral I packed up and moved out. Only recently i've been trying to get a good relationship back with my Father. I'm not going to say that I don't miss her every single day and that I don't hate my father but I am no longer crippled by her death."

I could not believe what Damon had just told me. I was crying even more imagining him having to go through that as a child. He was being so honest and I could tell that he had never told anyone all of that. What was different about me?

He placed his hand on my thigh and started rubbing soothing circles which were calming me down. He must have realised that this was wrong and quickly snached his hand away from my leg.

I don't know what it is about him but I want to know more. I want to know him.