A/N: Sorry it's been a while! I've been really busy. I have two jobs, two kids, and a house that is always messy. I meant to update way sooner. Anyway... I hope you enjoy this chapter. Thanks for your patience, and I hope you all have a great New Year!

"Ok," Caroline ate her eggs like she was eating popcorn at a theatre. "So, he gave you his jacket, he asked you to dance, and told you that you were beautiful, and you didn't hook up with him?"

"I am more than a one-night stand," I reminded Caroline. "Plus, he is the nephew of the CEO. If he wanted me gone because he didn't want to see me around anymore, I'd be toast."

"You're right, you're right," she agreed. "That was smart. I just admire your willpower."

"Believe me it was hard," I smiled. "Pun intended."

"Elena Gilbert!" Caroline giggled.

"Ok, I'm done," I surrendered. "How are things going for you?"

"Well…" She tried holding back a smile. "I met this guy"-

"What? Who? When and where?" I demanded answers.

"I met him at work, he was looking at tile samples," she smiled. "He's really cute and really sweet."

"What's his name?" I asked.

"Stefan," she beamed.

"Oh, my goodness that's awesome Care!" I was so happy for her.

"So, he mentioned he has a single brother," Caroline tried being sly. "Would you maybe want to go on a double date?"

"A blind date?" My eyes widened.

"Well Stefan's cute so I'm sure his brother is also cute," she tried encouraging me.

I thought about it for a minute. I wasn't the type to go on blind dates. I felt as though I didn't need them. But the more I thought about how much that wasn't working out for me, the more a blind date sounded appealing.

"Ok… what the hell," I shrugged.

"Really?" Caroline perked up.

"Why not?" I agreed.

When I got to the office on Monday, I was in a really good mood. I was happy to know that the only reason Damon was a jerk to me, was because he thought I was beautiful. So even if he went back to hating me, at least I knew the reason why.

I was brewing some coffee when Damon entered the breakroom. "Hey princess," he greeted taking a seat.

I didn't even need to look at him, "I see the snarky comments are back."

"Aw, you missed them, didn't you?" He said sarcastically.

I turned around to face him, "I'm having issues with the time off requests. They aren't all coming through."

"I'll take a look at it for you."

"Now?" I asked.

"Is that code for something?" he teased. "You need me to check your hard drive to make sure it works alright?" He smirked walking closer to me.

"I'm HR, I could get you in trouble for sexual harassment," I tried hiding my smile.

"I see that smile," he caught me. "You liked my nerdy IT joke."

"You've used that, before haven't you?" I asked. "Is that how you get laid around the office?"

"I never mix business with pleasure," he sounded serious. He reached around me to grab the coffee pot and poor himself a cup. "I don't fuck people I work with."

I flinched at his harsh use of words, "Well it's a good thing we didn't then. I'd probably be fired."

He poured me a cup as well, "I guess I can always fantasize then."

I grabbed the cup he handed to me and he followed me to my office. He sat down and started fiddling with my computer. "Do you have plans this weekend?"

"Why?" I asked.

"Just making conversation princess," he smirked.

"Yes, I do," I answered him. "And I really hate the nickname princess."

"What are you doing? And what would you like me to call you?" He turned his attention back to my computer.

"On Saturday I have a date, and Sunday I'm taking a new yoga class with my roommate and then were going to the winter carnival," I answered. "And Elena would be just fine."

"Elena is boring," he rolled his eyes. "And who's the date?"

I sat down next to him on my desk, "I don't know. It's a blind date. I'm going with my roommate Caroline. She met this guy at her work, he apparently has a cute single brother, so I'm not entirely sure."

Damon tried hiding his smile, as he clicked a few more buttons.

"Jealous?" I teased.

"Not at all," he smirked at me, like he had secret I didn't know. "Your computer is jacked," he turned to me. "I'll get you a laptop in the meantime."

"Ok," I sighed. "Did I do something wrong?"

"No, it's an old piece of shit," he promised.

"Just like you," I teased him.

"Ha-ha!" He stood up rolling his eyes.

He leaned down to my eye level, resting his palms on my desk, they rested next to my thighs. I had to lean back slightly so we weren't nose to nose. "Just a little advice for your date this weekend," he started to suggest. "Wear something red," he looked down at my lips. "I think you'd look really good in red." He let his lips fall to my ear, "You might even get laid princess," he whispered teasingly. He squeezed the top of my knee twice in a playful manor before leaving my office.

"I'll bring you a laptop," he turned around. "And then I'm going to come back and trash that computer."

"Thank you," I called over my shoulder as he left.

The remainder of the week was a lot of playful flirting. I looked forward to the few short moments we had. I had to admit, he was putting a smile on my face a whole lot. But I had to remind myself that, that's all it could be. He didn't do romance, and it wasn't a good idea to mix business with pleasure.

On Friday after work Caroline and I went shopping for our dates on Saturday. I ended up finding a short bright red dress. It was simple but the color made it stand out. Caroline found a green dress that complimented her figure nicely.

I was excited to go on the date. Hopefully he was cute, and smart, and nice, with a good sense of humor. On the other hand, I couldn't get Damon out of my head, and that was bothering me. It was never going to happen so why did I even think about him? I needed to stop the flirting so that I could date without mentally comparing them to him. He was starting to become a bad distraction, and I needed a clear mind.

Caroline and I drove to a bar that we were meeting them at. The night was cold, but it could be a lot worse that's for sure. The roads were clear and there was no chance of fresh snow. We had to walk a long way, but I was starting to get used to the freezing weather believe it or not.

"He just texted me," Caroline looked at her phone. "He said they're inside, waiting near the door."

"Ok," I took a deep breath trying to calm my nerves. I was praying that I wasn't totally awkward, and that he was interesting to me.

We finally entered the bar, and we removed our jackets. Caroline looked around, before spotting Stefan. "There they are," she smiled wide. "Follow me."

I was fixing my twisted strap as I blindly followed Caroline 10 or so feet. When she slowed to a stop, I looked up to who I can only guess was Stefan, based off of Caroline's detailed description. He was extremely attractive. I noticed he was alone, but before I could ask, he explained.

"My brother just ran to the bathroom quick," he gestured to the right. "You must be Elena," he extended his hand for a handshake.

"Nice to meet you," I smiled at him.

"Hello Caroline," he turned his attention to her with a smile.

"Hi," she flushed.

"You look beautiful," he gave her a quick scan.

"Thanks," she bit her lip. "You look very handsome."

They smiled at each other for a moment before Stefan led us to a high top. The waitress came over and we ordered our drinks. "Um, Damon will probably have bourbon," he told the waitress.

"Coming right up," she smiled before leaving.

Caroline snapped her head towards me. Damon? That would be an awful coincidence if they had the same name. Maybe it was the universe telling me something…

"Hey princess," I heard that all too familiar voice coming from the side.

There he was with a hardcore smirk, "I love the red," he leaned in to give me a kiss on the cheek.

"You've got be kidding me!" I looked at him.

"Oh, don't tell me you've already…" Stefan trailed off looking at his brother disappointed.

"Oh no," Damon patted him on the back. "She's a coworker of mine. You know I don't mix the two."

"I'm sorry," I looked at Caroline and Stefan apologetically. "Will you excuse us for a minute?"

I grabbed Damon by the sweater, pulling him far away from the table so they didn't have to hear me lay into him. "Ok," I spun to face him. "I spent a lot of money on this dress! I walked in these heels in the freezing cold because parking sucks here. And I'm wearing really uncomfortable, but sexy underwear!" I jabbed my finger into his chest. "And I'm on a date with Mr. I don't do dates?!"

"I don't," he smiled at me amused. "But once I figured out that it was you on this mystery double date, I had to come."

"So, you're doing this to torture me?" I crossed my arms.

"Well that's part of the fun," he teased.

"Unbelievable," I sighed exhausted.

I marched away from him and went to find Caroline and Stefan. They were all googly eyes and smiles at each other. "Sorry about that," I apologized to them. "You guys have a great time tonight; I'm going to make Damon drive me home."

"What?" Caroline sounded disappointed. "Are you sure?"

"Yes," I nodded.

Damon crept up behind me, grabbing my waist, "Just give us another minute," he said tugging me back away from the table.

"Ok look princess," he sounded serious. "I don't do dates, but here I am on a date. And yes, part of it was to get a reaction out of you. But I also can't get you out of my head. And I can't tell if it's because I just really want to fuck you, or if…" he trailed off. "I've never had a girl play hard to get, and it's driving me crazy. You're so hot and cold, and I don't know what you want. You're making me question what I want."

I uncrossed my arms surprised by his little confession. "I'm not sleeping with you tonight."

"I kind of figured," he stared at me.

"I don't trust you," I glared. "It's just a little game for you. Once you get what you want from me, I'll be just another notch in your belt."

"I don't know," he shrugged. "You're messing with my head. I can't say if that's true or not."

"You're an ass," I tried walking away from him.

"I'm sorry, I'm just trying to be honest," he grabbed my arm to stop me. "Look I know that I'm not going to get laid anytime soon, but I'm willing to go on dates with you to figure it out."

"Willing?" I glared. "What a noble sacrifice."

"I want to," he corrected. "I want to go on dates with you."

I looked into his eyes to see how sincere he was being, and there wasn't an ounce of sarcasm. "Fine," I sighed. "One condition," I said.

"Name it," he asked.

"We have to go on real dates. No hanging out at each other's places or hanging out in my office during lunch. I want dinner, movies, and adventure," I stated.

"Deal," he promised.

"And one more thing," I added.

"So, two conditions?" He smirked.

"If you are going to date me, I don't want you sleeping around. I don't care if you go on dates with other women, if you want to explore your options, but I don't want any dick dipping. The one-night stands have to stop," I stood tall.

"Dick dipping?" He snorted.

"If you want to sleep around that's fine, but then the dating stops," I warned him.

"I will hold off on the dick dipping," he promised.

"Ok," I was about to walk back to Caroline and Stefan.

"I have one condition as well," he blurted.

"And what's that?" I tried stifling a giggle.

"If I am going to be celibate for who knows how long, you cannot tell me things like your wearing sexy underwear," he groaned, as his eyes scanned my body up and down. "And maybe wear turtlenecks."

I giggled, "Ok I won't talk about my underwear anymore."

We went back to our date with Caroline and Stefan. We talked with them for a couple hours, laughing, telling stories about each other, and just having a good time. Damon and I gave them some alone time which resulted in them leaving together to go back to Stefan's place.

"I can drive you home," Damon laughed.

I was dumbfounded that Caroline left me without any warning and she took her car which was supposed to be my ride home too.

"It's not like she left me a choice," I laughed.

"We had to park far so I can go get my car, and pick you up at the entrance," he offered.

"No, I'll walk with you," I said as I put my jacket back on.

"You sure?" He asked.

"Yeah," I assured him as we walked outside into the cold.

He grabbed a hold of my hand as he pulled me in the direction to his car. "How can you walk in those heels?" he asked me.

"After a couple hours your feet become numb," I joked.

He laughed along with me, his hand still holding mine. He interlaced our fingers and rubbed his thumb along the side of my hand. "I had a good time tonight."

"Me too, surprisingly," I smiled.

"I can be a good time," he smirked.

"You and Stefan seem close," I observed.

"Yeah, he's alright for a brother," he joked. "When we were kids, he annoyed me mostly, but as he got older, he became more tolerable."

"How old are you exactly?" I already knew the answer thanks to Caroline's digging, but he didn't need to know that.

"31," he peeked at me from the side. "And I'm assuming you are a little bit younger than me?"

"23," I nodded.

He nodded his head, "Eight years," he mumbled.

"Is there something wrong with that?" I asked.

"Not with me," he shook his head. "Does it weird you out?"

"No," I was surprised it didn't bother me. "Besides women are more mature, so we're probably about the same," I teased.

"You think your hilarious, don't you?" he shook his head at me, before turning a corner.

We walked for another ten minutes or so, before he drove me back to my apartment. I learned more about him. I learned more about his parents and his family. He lives on his own and he has a house just outside of the city. He has a lab named Lucy and he hates his neighbors.

We pulled up to my apartment building, "Can I walk you inside?"

"You don't have to," I told him.

"I want to," he turned off his car.

"I'd appreciate that," I smiled before getting out.

He grabbed my hand again and let me lead him into the building.

"So, what about your family?" He asked.

I fumbled with the keys as I answered him, "I'll save that story for another date."

"Drama?" he wondered, as we walked inside.

"Just…" I didn't feel like talking about my dead parents. "Complicated."

He followed me into the elevators, dropping the subject. "This seems like a nice place."

"Yeah, it is," I agreed. "It costs an arm and a leg though."

"I bet," he smirked.

The elevator doors opened to my floor, and I suddenly felt sad. I didn't want it to end. I walked to my door and opened it with my keys. I set my purse on the counter and took my jacket off throwing it on the counter also. I turned back to Damon who looked incredible leaning against my door frame. "Thanks for walking me to my place."

"Anytime," he gave me that adorable, crooked grin. He pulled out his phone and handed it to me. "Can I get your number?"

I took it from him and entered in my information.

He took his phone back, "You are officially the first girl to be programmed in my phone."

"Really?" I giggled.

"Well…first girl that isn't a relative of mine," he corrected himself.

"Do you plan on using it?" I asked.

"Oh yeah," he nodded. "Expect lots of texts throughout the day. Especially when you're working," he teased.

"Oh great," I rolled my eyes.

"Feel free to send nudes too," he smirked.

I smacked him in the chest, "You're gross!"

He chuckled as I gave him a teasing glare. It was quiet for a minute, neither of us really wanting the night to end, but knowing it was time. He gently put his thumb and pointer finger under my chin. He tilted it up slightly so that I was looking into his eyes. He waited a few seconds trying to read my face. He slowly lowered his lips and pressed them to mine. And I thought I liked him before… Now I had a taste, and I wanted more. Like a drug addict needing another fix. I gently parted my lips, letting his tongue into my mouth. Our mouths danced like two familiar dance partners. Our bodies like magnets, drew closer. Our hands explored like curious teenagers. Sounds escaped my mouth I had never heard before. I wanted to pull him into my apartment and rip his clothes off, but my brain managed to remind me that it wasn't a smart idea.

I pulled away from him and our mouths made a sound as they detached, like suction cups that were pulled apart. "I told you, I'm not sleeping with you," I said more to myself than to him.

"I'm sorry," he apologized sincerely. "My brain just stopped working for a second."

"Mine too," I blushed, as our bodies were still smashed together.

"I'll call you later," he kissed me on the lips once more.

"I look forward to it," I smiled as he reluctantly pulled away from me.

"You and Stefan should come to the winter carnival tomorrow," I suggested. "Maybe we could run into each other."

"Hmm," he thought about it. "I just might."

"Good night," I smiled, wishing he could stay.

"Goodnight, princess," he smirked.

I stuck my tongue out at him, before shutting the door in his face, and locking the door.

"I'm in trouble," I whispered to myself.

A/N: What do you think will happen next? Please leave a review, so I can know what you're thinking. I hope you are liking it so far!