A/N: Thanks for the reviews!

I have to be honest... I'm feeling a little defeated. I don't think this is impacting people as much as I hoped it would. I am open to criticism, comments, pointers etc. But I don't there a lot of people interested. And that is totally fine! I'm not sure if it's worth it to continue this story... However, it is finished so I would like to get it out there, but if it's not worth it then it's kind of a waste of time.

Sorry for the pity party, I'm just very unsure of myself right now. I'm not looking for sympathy or even reassurance. I just want to know if it's worth my time to edit these chapters and post them, if there aren't a lot of people wanting it.

Anyways... I hope you like this chapter!

Caroline had returned home in the early morning and we went to our yoga class, before getting ready to go to the winter carnival. We were walking around viewing the ice sculptures and going to booths looking at cute Knick knacks and homemade scarfs and hats.

"So, you really like him?" I asked Caroline as I debated which hat to buy.

"I do," Caroline melted as she thought about him. "He was such a gentleman. I mean I would've jumped his bones, but he told me he wanted to take it slow with me. So, we made out for hours and hours, and then we just fell asleep in each other arms. It was perfect."

"That's adorable," My lip pouted.

I held up two hats unable to decide, "Which one?"

She scrunched her face in thought, "Grey one."

I handed the lady the grey hat and some cash.

"So how was your night with Damon?" She asked.

"Really good actually," I flushed.

"Details," her eyes widened.

"We talked a lot," I grabbed the bag from the lady, and we started walking towards the fancy decorated trees. "He held my hand all the way to the car, and then back up to our apartment. And then he kissed me."

"How was it?" She grinned.

"It was intense… and hot," I reminisced. "But it was also gentle and sweet."

"I'm glad that it went well," she smiled. "I was a little worried there for a second."

"Yeah," I couldn't help but laugh. "He sure knows how to push my buttons. But he's also really good at sweeping me off my feet."

Suddenly my phone pinged, and I dug it out from my back pocket.

You look hot ; ) -D

I looked around quickly and found Damon standing by the skating rink, with a smirk on his face. Stefan was with him.

"I may have told him we were coming here," I told Caroline.

"I am not complaining," she followed me to them.

"Hey, you," Damon greeted me.

"Hi," I felt like my smile couldn't get any bigger.

"Have you skated before?" Damon gestured to the skating rink.

"No," I shook my head.

"You want to give it a try?" He asked.

"Sure, it could be fun," I decided.

Stefan and Caroline went off exploring, while Damon and I tackled the ice rank. We rented some skates and ventured our way onto the ice.

Damon got on the ice first, turning around to grab my hands. He kept me steady as I shakily stepped onto the ice.

"You make this look so easy," I gripped onto his hands for dear life.

"I played hockey from the time I was 4, and then all the way through high school," he steadied me. "Of course, it's easy for me."

My legs were shaking as I tried to balance. Damon skated backwards, holding on to me so that I could move forward. "Look at me," he told me. "Don't look down."

I looked into his gorgeous eyes and felt so safe. "I'm really bad at this," I giggled.

"It's hard at first," he slowly started turning the corner and I wasn't prepared. My legs kicked forward, and my upper body went straight back. I pulled Damon with me, as I fell straight onto my back. Damon was able to help make the fall less painful, and a little more graceful.

He landed on top of me and he roared with laughter. His laugh made me laugh, it was quite adorable. "I'm sorry," I giggled.

"It's bound to happen," he smiled down at me. "You ok?"

"Yeah," I nodded. "I'll probably have bruise on my ass, but I'm fine."

"I can ice that for you later," he wiggled his eyebrows playfully.

I playfully smacked his chest before he helped me stand up.

"So…" he continued holding my hands as he skated backwards. "You said you'd tell me about your family on our next date."

I looked down, not wanting to have a dark could over this date that was going so well. But I had to get it over with, he was going to find out at some point. "When I was about to be a junior in high school, I was at a party and I had been drinking. I got in a fight with my boyfriend and so I called my parents to pick me up. We got in a car accident and I was the only one that survived," I tried detaching myself from the story as much as I could.

Damon's eyes filled with sadness. I could tell he was not expecting me to say that. "Gosh Elena, I'm really sorry."

I could feel the tears start to sting my eyes, and I willed them back. "My aunt Jenna moved in to take care of me and my brother Jeremy. I stuck around the area when I went to college for Jeremy's sake. Jeremy took a year off in between high school and college, and then he moved to LA to study art. So, I finished college, and I wanted to leave. I needed to get out of that town… of that state."

"Where are you from?" He asked.

"Virginia."

"Well, I'm glad you chose Minnesota," he smiled.

"Me too," I agreed. "It's quite different here. The city, the weather, the people."

He smiled, "Are you and Jeremy close?"

"We are," I shook my head. "I don't see him much obviously now, but we talk a lot. He's coming to visit me for Christmas in a couple of weeks."

"What were you like in high school?" he wondered.

"Oh jeez," I had to think about that. "In the early years I was the life of the party. A cheerleader,"-

"Nice," Damon smirked.

I shook my head and rolled my eyes. "I did well in school. But towards the end I was the sad girl. I tried to hide it and mask it, but I think everyone could see past it. I quit partying, I quit cheerleading, and I just focused on surviving."

"That's understandable," he assured me. His hands gripped mine, "Your hands are freezing. Let me buy you some hot chocolate."

"Ok," I smiled.

We walked to a concession stand, and he bought us both some hot chocolate. It was cutely decorated with a candy cane, whipped cream and shaved chocolate.

"I actually love the super cold weather," I said sitting down on a bench. Tossing my empty cup of hot chocolate in the trash.

"You're crazy," he shook his head. "I've lived here my whole life and I still can't get used to it."

I threw my legs across his lap. "It makes Christmas more festive. And it makes hot thinks more enjoyable, like coffee and hot chocolate, and tea. Plus, I love cozying up under a blanket, and looking out the window at a winter wonderland."

"Any excuse to cozy up to you," he rubbed my thighs creating friction to warm me up.

"Exactly," I smiled glad he was starting to see the good things about winter.

I was starting to shiver now that we were sitting still. He grabbed my hands, cupping them between his large ones, and he breathed his hot breath on them. He kissed my hands a couple of times before blowing on them again.

"Regretting the date?" I asked noticing he was just as cold as me.

He shook his head, "You're worth it."

"Next time I'll pick something warmer," I shivered.

"Please," he gave me his adorable, crooked smile.

My phone chimed so I retrieved it from my jeans pocket.

I'm freezing my ass off. I'm waiting for you in the car whenever you're ready. -C

"Looks like Caroline is ready to go," I told Damon.

"Ok," he helped me off the bench. "I'm glad I get to see you tomorrow."

"Me too," I blushed. "But we have to keep it covert. I know your uncle is fine with it, but I'd rather not deal with office gossip. So, no kissing, or hand holding, or ass smacking."

"I would say I'm more of an ass grabber, than a smacker," he smirked.

"I'm serious Damon," I warned him.

"I know," he rolled his eyes playfully. "I will keep my hands to myself."

I stood up on my toes to give him a quick chaste kiss. "I'll see you tomorrow," I smiled sweetly at him.

He rubbed his thumb back and forth along my cheek, "Have a good night, princess."

The next morning, I tried concealing my smile when I got to the office. I'm sure I looked like a kid on Christmas morning I was so happy. I had tried to stay in my office and focus on my work. I couldn't let him distract me from doing a good job. But then my phone pinged.

You look irresistible today. -D

When did you see me? -E

I smiled thinking about him checking me out.

I was updating John's computer and you walked by his office. -D

Well, you're going to have to resist. -E

I went back to work finishing up maternity leave paperwork for Haley and dealing with some disability work for Andrew. I was swamped all morning, so when lunch rolled around, I was surprised by the time. When I left my office, it was quiet on the floor. There were a couple people eating in their office, and some eating in the breakroom. Most people left to go get lunch. I walked down to Damon's office to see if he was there.

When I entered his office, he was on the phone talking to someone. He gave me a crooked smile, acknowledging me. I shut the door behind me and came to sit on his desk. He sounded like he was talking to someone from work, so I proceeded to tinker with the things on his desk.

"Ok, I'll come take a look after lunch," Damon spoke into the phone. "It's probably a virus."

He exchanged a few more words and then hung up the phone. "I was beginning to think you were ignoring me," Damon looked up at me from his chair.

"I was just really busy this morning," I assured him.

His hand reached out to rest on my thigh but then he pulled it back, remembering my rules. "This is going to be a long week," he almost growled. "You make it hard for me to focus."

"That's exactly why I stayed in my office all day," I giggled.

"I kept trying to find excuses to come to your office, but everyone's been really needy today," he rolled his eyes.

"That's ok, I had a lot to do, and I'm sure I wouldn't have gotten it done if you were distracting me," I said honestly.

"What are you doing for lunch?" He asked.

"I brought one," I bit my lip.

Damon sighed, "Save it for tomorrow."

"I don't want people getting suspicious," I shook my head.

He stood up and threw on his jacket, I could tell he was in deep thought.

I stood up off his desk. "Would you want to come over on Friday after work?"

"I thought that was against your rules?" He reminded me.

"Well one time is fine," I shrugged. "I could cook you some dinner and we could rent a movie."

"I'll think about it," he winked at me.

My hand fiddled with his tie, "please?" I gave him my best puppy eyes, and pouty lip.

"You are making it really hard to not kiss you right now," he groaned.

"I guess we will have a lot of making up to do on Friday," I bit my lip.

His hands grabbed my hips and he pushed me back against his desk, his body pressed against mine. "I can't concentrate when you play with my tie like that," his eyes got dark. His hands squeezed my hips, like he was trying to release some tension. "And please stop wearing tight dresses to work."

I wanted to kiss him so bad. I wanted to make out on his desk and rip the shirt off his body. I wanted to lick his neck and claw his chest. And make out until our mouths were red and swollen.

He quickly released his grip on me and left his office without a word.

"Are you thinking you'll be here next weekend?" I asked Bonnie as we facetimed.

"Yeah, we just bought our plane tickets this morning. We will stay for three nights and then we will leave early Monday morning," she explained.

I buzzed around the kitchen, checking on my lasagna, and mixing up a salad. "Ok I'll sleep with Caroline and you and Jeremy can have my bed. Just please don't have sex in it," I grimaced.

Bonnie laughed, "I'll try not to."

"I'm so excited to see you!" I smiled just thinking about seeing them in person. It's been months since I've seen them. I had gone out to LA before I left for Minnesota, but that was back in August.

"Me too," Bonnie sighed. "Jeremy is excited too."

"It's been forever!" I exclaimed as I finished up some last-minute cleaning.

"You must be nervous," Bonnie noticed.

"Well… He's never been to my place before, other than the doorway. I need to make sure it looks nice," I lit a candle in the bathroom. "I'm more nervous about the conversation I have to have with him tonight."

"Oh yeah," Bonnie clicked her tongue. "I'm sure it'll be fine. He'll probably find it to be a huge turn on."

"I don't know about that," I sighed.

"it'll be fine," she promised. "I still haven't seen a picture of this guy yet."

"He is seriously so hot," I smirked.

Suddenly I heard a knock at my door. "That's him, I'll talk to you later."

"Oh, just let me get a little peak," she begged.

"Sorry," I bit my lip. "I'm not going to freak him out. Bye!" I ended the facetime.

I opened the door, and there he stood hot as ever. "Hi," I could feel myself blush. "Come in."

He walked inside and took off his jacket, and I hung it up in the closet. "Smells good in here," Damon said.

"It's almost done," I smiled at him.

He pulled me in for a hug, and I just about melted. He smelt amazing and his arms were big and strong. He wore a plain black t-shirt and jeans. I thought he was sexy in dress clothes; he was dripping with sex in just casual clothing.

My oven dinged, indicating the Lasagna was done. I served us up some dinner and poured us some wine. "I hope you like wine."

"I do," he took a sip after I served our food. "Where's Caroline?"

"She's at your brothers," I said.

"They seem to be hitting it off," he wiggled his eyebrows.

"Yeah, she really likes him," I smiled, happy for them.

"I think the feeling is mutual," Damon took a bite of Lasagna. "This is delicious."

"Oh thanks," I bit my lip. "Caroline actually made it before she left. I'm a terrible cook."

Damon roared with laughter, "Well I appreciate the honesty."

"I'm trying to get better," I laughed along with him. "But I am not a natural."

"Tell Caroline she is a great cook," he smirked.

"I will," I giggled. "So, what movie did you pick out for us?"

"I didn't know what you liked so I got 3," he shrugged. "I got a romantic comedy, a scary one, and a drama."

"Definitely scary," I said before taking another bite of lasagna.

"That surprises me," he admitted.

"Really?" I asked. "Which one did you think I'd choose?"

"The romantic one," he smiled.

"I'll probably want to watch that one right after so that I don't go to bed all freaked out," I admitted. "But I love a good scare."

We finished our food and then I quickly cleaned up our dinner while he got the DVD player set up. "I want to talk to you about something, before we start the movie," I walked over to Damon, as he sat down on the couch.

"Ok," he turned serious.

I sat down next to him, and I could feel the anxiety rise in my chest. I looked down at my hands, unsure about how I was going to say it. Should I just blurt it out, or just explain myself first?

He must have sensed my nerves, because he pulled me in closer to him, "What's going on?"

"There is just something you should know before we continue dating each other," I kept my look down. "It just might be a deal breaker, and I would rather you end things now before we get too…" I let my sentence fade out.

"Elena," he barely whispered. "You're freaking me out, just say it."

I looked up into his eyes, and it felt like a knife to the stomach. His eyes held so much concern and it made me feel awful.

"Look…" he started. "Unless you're wanted for murder, or secretly married, you're not going to scare me away." He tucked the hair hanging from my face and put it behind my ear.

I took a deep breath, "I'm a… virgin."

"Oh," you could see the surprise on his face. "For real?"

"Yeah," I could feel my cheeks reddening from embarrassment.

"Are you waiting for marriage?" He asked.

"Not necessarily," I shook my head. "I'm just waiting to be in love."

"Have you… done anything?" he asked.

"I had one serious boyfriend in early high school, that I've done pretty much everything but sex with," I fiddled with a loose thread on his t-shirt. "But since then, I haven't really. Besides one drunken night in college I…" My face flushed. I may be good at flirting, but I was still very innocent. "gave a guy…" I don't know why I couldn't say the words, I was 23 for crying out loud!

"I can fill in the blanks," he finally said.

I felt like a child. And I was afraid the age difference, and lack of experience was more than apart to him now.

He lifted my chin and gave me a gentle sweet kiss. "I'm surprised," he admitted. "But it's endearing."

"Did I scare you off?" I asked.

"Not at all," he shook his head. "I mean… it makes me a little nervous. I mean you have to know I am the complete opposite. I've had lots of sex, and I'm not saying that to intimidate you, I just want to be as honest as I can with you." He held eye contact with me, wanting me to really understand what he was saying. "I've never been in love before; I've never even had a girlfriend. Not even in high school. And what scares me is…" he stopped to think about his words carefully. "You want to be in love. And losing your virginity is a big deal, especially when you waited this long. And… I want to be careful with you."

"What do you mean by that?" I asked.

"I like you. A lot," he played with my hand, interlacing our fingers. "I just don't want to hurt you."

I could feel my heart race. I already knew that was a possibility. He was pretty much emotionless when I met him. And because I haven't slept with him, I intrigued him. "Do you think… You only like me because I haven't slept with you?"

"No," he answered immediately. "I mean I thought that at first, but I know that if we had sex right now, I'd still want you after."

"Then why are you scared of hurting me?" I wondered.

"I don't want marriage or kids," he reminded me.

"I mean I can understand the kids' part, but I…" I felt like this turned very serious, very fast. "What's so bad about marrying someone you love?"

"I just don't… I don't know if love is in my future," he confessed.

"Are you saying you don't think you could fall in love with me?" I could feel the stupid tears starting to sting my eyes. I tried so hard to fight them. I mean this is our third date, I hardly know the guy. I shouldn't be so hurt.

"Don't look at me like that," his face twisted in pain. He grabbed my face, and wiped the underneath of my eye, as a tear spilled over.

I pulled his hands away feeling like an idiot for crying. He probably thought I was absolutely nuts. "I'm sorry," I apologized for crying. I took a deep breath and blinked away the moisture.

"Look," he rested his forehead against mine, "it's not that I don't think I can fall in love with you. I mean you're already making me feel things I've never felt. I mean if this was any other girl talking about love, I would've walked out, deleted their number and never spoke to their crazy ass again. I'm a dick," he played with my hair. Repeatedly stroking it out of nervous habit. "But with you… I'm terrified. I know that you are already doing crazy things to my heart baby."

I smiled at his little confession.

"I just don't want to get married," he reminded me. "So, two years from now if were still… together. I don't want you to hate me for still not wanting marriage."

"This is crazy," I sighed. "Were talking about something so far in the future."

"But I need you to hear me loud and clear," he looked me in the eye.

"What about what I want?" I could feel that familiar anxiety creeping in again.

He sighed not having an answer for me.

"I guess I should end it now then," I said the words, not wanting that at all.

I could see the hurt in his eyes, "Is that what you want?"

"No," I chocked. "But it's probably the smart thing to do. If It hurts now, it's only going to be ten time worse down the road."

"So, am I supposed to look at you at work every day for the rest of my life? Wanting to kiss you and hold you? Watch you move on one day…" he trailed off.

"I want to be married someday," I said honestly. "I'm not saying anytime soon, but I do eventually. And if that's not a possibility for you then you can't ask me to sacrifice that."

"I know…" he seemed to come to grips with the inevitable. "I want you though."

"What is it that scares you so much about marriage?" I straddled his lap. He was taken aback by the closeness. He rested his hands on my hips though.

"I don't know," he said honestly.

"Is it having sex with one person for the rest of your life?" I wondered.

"No," he shook his head. "Especially if it's you."

"Is it living with someone? Sharing finances?" I listed the possibilities.

"No," he answered.

"Then what is it?" I looked down into his eyes.

"I don't know…" He seemed agitated. "I guess…" he was looking for the words. "It's the immensity."

"Immensity?" I needed further explanation.

"Marriage is hard, it gets ugly. People change, they cheat, they lie… They become monsters," he sounded serious.

"Yeah, it can be ugly," I agreed. "But" my hands snaked through his hair and I looked deep into his eyes. "If two people really love each other, they'll do everything in their power to be the best versions of themselves. And sure… They'll slip up… probably a lot. But as long as there is love and trust and honesty, they'll be just fine."

"Yeah," his face still had a lot of doubt.

"I don't want to force you into a relationship if you don't want that," I released my hands from his neck. "And it's clear that we don't see eye to eye on relationships,"-

"Don't," he gripped my waist.

"Damon," I exhaled. "It's inevitable."

"Elena," he sighed.

"We were doomed from the start," I admitted to myself. "We knew it from the beginning, and yet we ignored the warning signs."

"Wait"- he tried, but he didn't even know what to say.

I got off his lap trying to use my brain. I had to do it. It was the right thing to do… no matter how much it hurt.

"Don't make it worse," This time the tears couldn't contain themselves. "It's fine, it's life."

"This isn't what I want," he sounded defeated.

"I don't either," I agreed. "But it's better this way. It'll suck for a little bit, but then we can go back to normal. You can… sleep with whoever you want. And I can find someone that wants the things I want."

"I don't want anyone else," he sounded agitated. "Not after meeting you."

"I want someone who wants to commit to me. Physically, mentally, emotionally, spiritually, legally," I wiped the fallen tear on my cheek.

He stood up off the couch and walked past me. He grabbed his jacket from my closet and threw it on.

I felt bad for having to be the one to say the words, but he was breaking my heart just as much right now.

He finally looked at me after opening my door, "I'm sorry," he choked. And I swear I saw tears in his eyes. But he turned before I could get a good look. Hearing the door shut was like I had just been shot. I let the sobs tear through my body, and I collapsed on the couch, letting all the painful feelings course through my body.

A/N: I still have a lot left of this story! This may seem like the tipping point, but there is still a lot left.