Elena's POV-

I picked up my cherry red lipstick and smoothed it over my lips. I smiled at my reflection. Today, I am going to tell Stefan that I like him. It's been a few weeks and I want to take our relationship to the next level. "Elena you ready to go?" I was at my vanity getting ready before Bonnie yelled for us so she could drive Olivia and I to the Salvatore Boarding House. "Yup! We're ready" I yelled as I walked down the stairs.

"Hey Lena?" Olivia walked out of her room but stopped at the door frame and leaned on it.

"Yep?" I placed my hand on my hip.

"Do I have to go?"She asked smiling but I could tell she was groaning on the inside.

"Yep" I answered with a smile on my face.

"Bu-" She started. I just glared at her.

"Fine..." Looked at me with her hands up. She rolled her eyes. We both walked down the steps and climbed into the car.

I know that Stefan and Olivia are close so I thought that if she came it would be easier to talk to him rather than by myself.

I walked up to the Boarding House looking at the intimidating doors. You can do this Elena. Just as I was about knock the door was open. I crept inside calling Stefan name.

"Stefan? Anyone home?" I yelledish.

"Hi!" A man walked towards me smirking.

"I-i'm sorry for barging in the d-door was-" I looked back it was closed "Open..." I breathed out.

"You must be Elena."

"Yup, thats me" I chuckled. "So... Do you know where Stefan is?" I asked smiling.

"He is right up stairs." He gestured pointing at the stairs. "Stefan! We have a visitor!" He called.

"And who might you be?" I rose an eyebrow.

"I'm Damon, Stefan's Older Brother." I shook his hand.

As I waited I texted Olivia to join me instead of waiting in the car because it was getting a bit awkward. I walked into the living room. But was stopped by Olivia's voice.

"Elena... " Olivia was looking for me at the front door.

"Here" I waved my hand.

Olivia's POV

As I walked into the house I saw beautiful antiques everywhere.

"Olivia! Meet Damon." Elena said. Damon... Nope never heard of that name.

"Hey I'm Olivia!" I said putting out my hand for him to shake.

As I looked up I caught a pair baby blue eyes with my own ocean. He looked at me and his smile dropped from his face. He looked surprised to see me.

"Olivia... H-Hi I'm Damon, Stefan's older brother" He simply said while shaking my hand. Just as I was thinking where I knew him from. I casually walked into the living room amazed.

"Wow...This is your living room?" My mouth was gaping open. Damon walked with me.

"Living room, parlor, Sotheby's auction. It's a little kitschy for my taste." Damon says, then looks at Elena. "I see why my brother's so smitten. It's about time. For a while there, I never thought he'd get over the last ones. Nearly destroyed him."

"Last ones?" Elena asked

"Yeah. Katherine and Re-" He was stopped by Stefan

"Elena, Olivia! I didn't know you two were coming over!" Stefan was walking down the stairs eyeing Damon.

"Oh, yeah. I wanted to talk to you but it seems you have a brother visiting that I never knew about" Elena said in a cold way but smiled never the less.

"About that...sorry I didn't tell you, I just didn't think you would care." He resumed.

"He also doesn't like to brag" Damon added in. I giggled.

I was still thinking about where I've seen those eyes from. I didn't realize I was looking at Damon this whole time.

"It's not polite to stare Liv!" Elena nudged me (not very softly I might add).

"Oh it's okay. It happens a lot" he smirked.

"I guess I could see why" I said under my breath as Elena was trying to persuade Stefan to talk to her.

"Elena, I have to go meet up with my uncle so if you want you can stay but I won't be here" Stefan said clearly trying to get us out of the house.

"Um okay... I think I'll be going. See you at school?"

"Yeah" Stefan sighed.

"Well that wasn't awkward at all" I whispered towards Damon. He instantly Grinned. He kissed my hand slowly and looked into my eyes. "I hope I'll see you again, Ms. Olivia" I blushed. Then I followed Elena out of the door and into the car.

Damon's POV

I stood by the bar drinking bourbon. The stinging feeling down my throat made me feel good. A car pulled up and I used my heightened speed to run to the kitchen. "Stefan? Anyone home?" I could hear Katherine's voice but I knew it wasn't her's. The voice was much more... nice. I decided to walk out of the shadows.

"Hi!" I smirked walking towards her. She looked exactly like Katherine.

"I-i'm sorry for barging in the d-door was-" She looked back and it was closed "Open..."She looked nervous so I just smiled at her.

"You...Must be Elena" I watched her shuffle around

"Yup, that's me." She chuckled fiddling with her jacket. "So...Do you know where Stefan is?"

"He is right up stairs." I gestured pointing at the stairs. "Stefan! We have a visitor!" I called knowing Stefan would be annoyed.

"And who might you be?" she rose an eyebrow. Looking up at my eyes

"I'm Damon, Stefan's Older Brother." I shook her hand smirking. While we waited I saw her texting someone on her phone. I saw she was fascinated by our living room but before I could say anything the door opened.

"Elena..." I saw Katherine enter the room. Curly hair and everything. She was looking around.

"Here" Elena waved her hand

"Olivia! Meet Damon." Elena said.

"Hey I'm Olivia!" She smiled I looked at her with my eyes wide. It was the drunk girl. My smile dropped. Katherine was still in that tomb. Helpless.

"Olivia... H-Hi I'm Damon, Stefan's older brother" I said while shaking her hand. She casually walked into the living room amazed. I smirked walking behind her and Elena.

"Wow...This is your living room?" Her mouth was gaping open.

"Living room, parlor, Sotheby's auction. It's a little kitschy for my taste." I said, I then look at Elena. "I see why my brother's so smitten. It's about time. For a while there, I never thought he'd get over the last ones. Nearly destroyed him."

"Last ones?" Elena asked me frowning

"Yeah. Katherine and Re-" I was stopped by Stefan walking down the stairs

"Elena, Olivia! I didn't know you two were coming over!" Stefan was glaring at me but I just smiled

"Oh, yeah. I wanted to talk to you but it seems you have a brother visiting that I never knew about" Elena said in a cold way but smiled never the less.

"About that...sorry I didn't tell you, I just didn't think you would care." He resumed.

"He also doesn't like to brag" I added in. Olivia giggled. When Stefan and Elena were arguing I could see Olivia staring at me from the corner of my eye.

"It's not polite to stare Liv!" Elena nudged her. She winced.

"Oh it's okay. It happens a lot" I smirked. I already like this version of Katherine!

"I guess I could see why" She said under my breath. She thought I couldn't hear her but my super hearing helps

"Elena, I have to go meet up with my uncle so if you want you can stay but I won't be here" Stefan said clearly trying to get them out of the house.

"Um okay... I think I'll be going. See you at school?"

"Yeah" Stefan sighed.

"Well that wasn't awkward at all" she whispered towards me. I chuckled. I kissed Olivia's hand slowly and looked into her eyes. "I hope I'll see you again, Ms. Olivia" She blushed. Olivia followed Elena out of the door and into the car.

Elena's POV

I awkwardly wobbled over to Bonnie's car and saw her playing a game.

I cleared my throat to get her attention and she instantly looked up at Liv and I.

"How was your talk?" Bonnie asked "Tell me everything!"

"Don't look at me" Liv replied with her hands up.

"His brother was there and I felt like they had some unfinished business to take care of" I lied.

"Oh. Well Boring!" Bonnie groaned

"Maybe next time.." I sighed.