A/N: Sorry for how long it took me to update, I've been busy with school and then working retail over the Holidays which meant no free time! I was stuck in such a writer's block when I wrote this chapter so if it sucks you can say so. Next chapter will hopefully be soon!

Caroline stood in the doorway too shocked to respond. How could Elena be so stupid as to bring Damon along? Damon had been given a free pass once with Sam and Dean but as Caroline stood there staring back at a grinning Damon she didn't think today was going to be his lucky break once more.

"I'm so sorry Caroline but I'm not allowed out of Mystic Falls without a baby sitter apparently and Stefan is a little tied up right now." Elena mumbled through gritted teeth.

It was nice to see Elena was just as tense as Caroline felt. This was supposed to be an easy, fun filled holiday, not a Damon crashing, near death match experience holiday. While Caroline continued to struggle with all the information thrown at her, Dean appeared by her side, looking annoyed but not angry. Caroline stood completely still as she watched Dean's face hoping for some hint to how he was feeling. Dean crossed his arms over his chest as he glared at a still grinning Damon.

"Dean it's so nice to see you. You must be having a hard time teaching little miss bad ass Barbie manners because she still has yet to invite me in." Damon mocked as he continued to smile at Dean.

"Come in." Dean said clearly annoyed.

Caroline turned wide eyes to Dean, completely at a loss. Why was he so nonchalant about all of this? Damon's smile grew as he crossed the threshold, taking exaggerated steps into the entryway. Elena followed behind him, her expression giving off the tension she could feel in the room.

"So Dean, made any deals with the devil lately?" Damon said as he passed Dean, a wicked smile across his lips.

Elena and Caroline's jaws dropped simultaneously as they watched Damon glide down the hall, making himself at home. The two girls turned to find Dean still annoyed, yet completely calm considering the circumstances.

"You're hilarious Damon." Dean mumbled under his breath.

"Aw, too soon?" Damon's voice echoed through the entry way.

Dean just shook his head and turned to make his way back to the kitchen. Caroline flashed Elena an awkward smile before rushing after him into the kitchen. Caroline stopped in the entry way to the kitchen to find Dean sitting at the table sitting next to Damon, still tense but not as annoyed as she assumed he should be. Caroline found some comfort when she took in Sam's shocked/tense expression. Sam looked as if he was ready to attack at any moment. Knowing Sam had the right idea made Caroline feel a bit better about the situation for some odd reason.

Elena walked past Caroline into the full kitchen and took a seat next to Damon, smiling awkwardly as glanced up at Caroline who still stood in the entryway watching the scene in front of her.

"This is Damon, he's a friend of Elena's." Dean explained to the table as he tilted his head to the man next to him before taking a swig of the beer in his hand.

"Oh is that what he is?" Caroline mumbled as she moved across the room, returning to her place in front of the stove.

"Is Caroline in charge of dinner?" Damon spoke behind her, humor thick in his voice. "Someone better call for Chinese."

Caroline whipped around and glared at the grinning vampire. "If you're offended by my cooking, that I have slaved over for hours now, you can always go home. I bet there's a barstool in Mystic Falls calling your name."

"Well, someone woke up on the wrong side of a Winchester." Damon retorted as he smirked at Caroline.

Before Caroline could say another word, or dive across the table and stake Damon, Dean cut in.

"Damon, didn't you say you were interested in cars?" Dean hinted, trying to draw the man away from the room of stares.

Damon glanced at Dean looking bored. "No, I never said that-"

"Just come on." Den sighed, seeing Damon wasn't going to make this easy.

Damon shrugged and followed Dean out the back door and into the yard behind the house. After a few steps away from the house Dean stopped and turned to Damon looking annoyed.

"Look bloodsucker, I don't know why you're here and I don't care but stop baiting Caroline."

"Worried you're not gonna get laid if this day goes sour?"

Dean broke out into a grin as he shrugged. "I mean that too but- wait" Dean shook his head, now his stern expression back on his face. "This isn't guy bonding, just cut the crap. I've got more shit to worry about than you playing ass hole checkers with Caroline."

"Wow, lame come back dude." Damon said looking at Dean like he just failed a test. "It doesn't matter anyways. It's not like she's gonna remember this Christmas in a few months. She's gonna think she spent it at home with Elena and the all American boy."

Dean stared at Damon as an ache swelled in his chest. "I didn't make this arrangement just so you could dick around."

"What arrangement?"

Dean and Damon turned to find Elena stand a just a few feet away, staring at the two of them in horror. Damon frowned as he stared at Elena, a feeling that may resemble guilt flooding his insides. Dean racked a hand through his hair as he stared at Damon, looking for some help.

"It's just a silly bet over football. You know guy stuff." Damon said as he grinned innocently at Elena.

"Damon." Elena said, that one word filled with so much conviction.

"I asked Damon to erase Caroline's memory." Dean said, as he stared at Elena, his eyes empty of emotion.

Elena stared at Dean, shocked. "But…why? That doesn't make any sense."

"Because I'll be gone in by May." Dean stated matter-o-factly.

Elena stared at Dean as she tried to wrapper her head around this information. None of it made sense. All the work Caroline was putting in, everything she sacrificed this year, and she wouldn't even remember it?

"You can't just leave her. After all she did for you, after giving up school and moving around all the time. You're just going to dump her? Just like that? Why wait until May?"

Dean stared at Elena, looking confused. "She didn't tell you?"

Elena ignored his question and continued on. "I knew when you showed up back in town she should have sent you packing, that you were just gonna throw her aside like she was nothing all over again but she was just so determined. She spent months crying over you when you left. I have never seen Caroline so broken up about some guy before and you're not even-"

"Elena," Damon stopped her mid-sentence. "Elena, Dean…he's dying."

Elena stopped and stared at Dean, now speechless. Now she was even more confused than she had been before. She just stood there motionless as she watched Dean stare at the ground, a humorless smile across his lips. When she turned to look at Damon she was shocked to see the remorse clear in his expression.

Dean was the first person to break the silence. "I sold my soul the devil and I was given a year to live. I want to know Caroline is going to be okay when I'm gone and I don't want her to spend the rest of her life searching for a way to bring me back. I know I'm being selfish, this year with her…it's more for me than it is for her, well, at least it will be. I wish I could regret going back to her Elena, but I just don't."

Elena felt her eyes begin to burn as she watched Dean. It was all too much, Dean dying, Caroline being left alone, Caroline forgetting that for a whole year she was happy. Thinking of Caroline losing so much…Elena just couldn't let this happen.

"Call it off Damon." Elena snapped, her voice full of anger. "You can't just let her forget all of this. I don't care what you think Dean. Caroline may be too stubborn to say it, but she loves you and being with you means something. Don't take that away from her."

Before Dean could say anything Damon cut in. "I'm not calling it off Elena. He's right, if you want Caroline to live her life she has to forget Dean made this deal. If she doesn't she'll go chasing after a solution until she dies. She's annoyingly stubborn in everything she does."

That was when Dean had had enough. "I'm going back inside, I'm not spending my day fighting with the two of you. I'll give a damn about all this another day, but right now I'm gonna go spend time with my girl."

Elena watched as Dean walked past her and into the house, his shoulders slumped in defeat. She could see the sadness in his eyes as he walked by, the pain so raw in his expression it made Elena want to cry.