Disclaimer: Supernatural © Eric Kripke, The Holiday © Nancy Meyers

Author'sNote: PLEASE READ! This fanfiction is based off of the movie The Holiday by Nancy Meyers! 'Definitely Unexpected' is the name of one of the songs on the soundtrack, FYI.

I'm not the first to come up with the idea of using The Holiday as a Dean/Cas story, but I wanted to share this anyway! I recently read AlreadyPainfullyGone's story and fell in love with their version. Definitely a great read! I also recently watched The Holiday again and wanted to see what it was like to focus just on the Dean/Cas part, instead of splitting it into 2 love stories. I loved the idea of Dean being the one traveling overseas etc.

Since this isn't a 2 love story kind of fic, I decided to go with Anna as the one Dean is changing places with. I don't know why, but she seemed more suited than anyone else I tried to think of. Plus, when she had her memory of being an angel wiped when we first meet her on the show, she seemed like the sweet little innocent type to own a cottage. Mainly due to how her human parents raised her. Anyway, I'm rambling...

I'm hoping to have everything finished by Christmas, since this is a Christmas related story. Putting rating as M since things will get smuttier later on.

Kept some of the lines from the movie more towards the end/in the instant messaging part.

Alright, now I'm finished! Enjoy!

Dean Winchester was never one for holiday traditions. That said, it didn't come as a surprise when he'd decided to spend the Christmas season by himself. What did come as a surprise, however, was that he'd decided to spend it overseas in a country he'd never seen, other than in cliché movies and cheap photographs.

Had someone told him that his life would've been turned upside down in said vacation, he may have reconsidered his rash decision to pack up and leave within the span of 24 hours. Unfortunately for Dean, though, life just wasn't as cut and dry as he'd always hoped.

He'd woken up that morning with a head ache and a bad attitude, which as of late seemed to be a daily occurrence. However, that particular morning something inside him finally snapped, and he began to question most of his choices in life. Why? He wasn't sure if it was the fact that the hired gardeners chose the crack ass of dawn to start their work outside his bedroom window, or the fact that he'd woken up in the ungodly hours of the morning to find his girlfriend of 2 years sneaking back into the house after her supposed "late night of working."

At the time he'd chosen to ignore it and went back to bed, but when he awoke again to find the other half of the bed empty, appearing to not have been touched at all, and said girlfriend asleep on the couch, he began to think back to the previous nights he'd woken up to a similar sight. Lisa hadn't exactly been the love of his life when he'd first met her. He'd been in his 'bad to the bone' stage in his early 20s and had enjoyed his fair share of sleeping around with random women, Lisa included. It hadn't been until they'd chanced a second meeting a few years afterwards that they'd decided to try out a more serious relationship. It'd been working out fine for the first year, but as Dean looked back on the most recent one he began to notice how far apart they'd grown.

He really started to reconsider the whole relationship piece. Perhaps random one night stands were just his thing.

Dean had been pacing the length of his bedroom as he thought on everything Lisa related. Over the past year she seemed to be more distant. That, and he was fairly certain that she was cheating on him. It was quite obvious, actually, considering she'd come back reeking of some other dude's cologne.

Dean ran his hand through his hair and scoffed when I started to piece together everything. He could feel his heartbeat pick up pace and his skin felt like it was burning. Yep, he was pissed.

He heard footsteps making their way to their—scratch that—HIS bedroom. He wasn't sure if he was ready to face her just yet, so he busied himself by pulling out a pair of pj pants to put on. Dean rolled his eyes when the door opened, Lisa made no move to walk into the room. It was like she was afraid to enter.

'Damn right, she should be.' Dean thought to himself as he pulled out a t-shirt to put on as well.

"So, ya have a fun time 'working' last night?" He barked at her, glaring daggers as he turned around.

Lisa sighed and leaned up against the doorframe, crossing her arms over her chest. "Dean, I don't know what you're talking about."

"Like hell you don't!" He yelled at her as he started pulling out her clothes from his dresser. It was at the point where all he considered her possessions to be the stash of clothes she kept at his place...and even then Dean technically owned them since he was the one who bought them for her in the first place!

"Dean what are you doing?" Lisa ignored his last statement as a worried look made its way on her features.

"Well, I'm taking your clothes out of my dresser, to give to you to take out of my bedroom, so that you can leave my house. See it was SUCH a good idea that we didn't fully move in together." He said sarcastically as he began flinging her clothes out of the door and into the upstairs hallway.

"Dean seriously stop being so childish! I told you I had to work late!" Lisa said exasperated as she too began picking up her clothes, though she had every intention of putting them back. "What's with you? Lately you don't trust me with anything."

"Ha, right. Well when you start being honest and quit lying about sleeping with your assistant, maybe then I could trust you." He stormed into the adjoining bathroom, before popping his head back out around the corner, "Which, by the way, super classy." Dean said sarcastically as his eyes narrowed. Did she really think he was that dense?

Lisa's cheeks flushed, whether in anger or embarrassment, Dean didn't know. He almost cringed at the icy glare she sent him, but he held her gaze with as much, if not more, intensity. Almost instantly their argument flared up even more, insults and past experiences were flung left and right as they both tried to validate their point.

"I told you that I had to work late, afterwards everyone decided to go out for a few drinks and wind down. Just because he happened to be there, doesn't mean we had sex!" Her nostrils flared as she spoke.

"Yeah, working until 2 am and then staying out for an extra 3 hours? Highly unlikely! How stupid do you think I am!" Dean punched the wall, trying to contain his anger.

"By now I'm starting to reconsider any past ideas I had of you being even remotely smart, especially after an assumption like that!" She retorted, following him as he stomped down the hall.

"Oh and by the way, why is it that I can't work overtime, always getting shit for working late during any day of the week, while you can skip out on dates and dinner plans all of a sudden because you were magically called in after hours? Huh? Doesn't that seem a bit unfair, and not to mention suspicious?" Dean twirled around so he could look her straight in the eyes.

"Are you seriously trying to pull that on me? You work 70 plus hours a week, there's no stopping you when it comes to you doing your stupid movie trailers! You moved a recording studio into your house so you can work when you're not at work, and you practically sleep with your blackberry! Me taking a few extra hours at work shouldn't be a problem!" Lisa fumed as she threw her hands in the air in defeat.

Dean was beginning to think that perhaps he was wrong about Lisa sleeping with...what was the dude's name again? Tony or something? She didn't falter once during their argument and she had a comeback for every incident he tried to bring up.

"Yeah, and what about last weekend when you all of a sudden were called into work when I know full well that your company doesn't schedule anyone for the weekend? Then you come back reeking of some cheap ass cologne, and don't think I didn't notice your little love bite on the back of your neck." Dean pushed her hair away to reveal the large purple mark, that definitely was not a birth mark as she claimed it to be.

"Jesus Christ! I told you the last time, we didn't sleep together! He's got a wife for crying out loud! Do you seriously think I would be that stupid to go messing around with some guy who's only been apart of the company for 6 months? For ANY guy for that matter!" Lisa picked up one of her sneakers that had bounced down the stairs. Her knuckles were white as she clutched it tight. "Have you ever considered that maybe you're just insecure and your mind comes up with these ridiculous stories?" She chucked said shoe at him and was disappointed when he dodged it.

"Right, does he tell you to say that to keep things hush hush? Or did you manage to come up with that on your own?" Dean pushed his way past her and flung the front door wide open, gesturing for her to leave.

Lisa shook her head as she stormed out, "You're so incredibly—" But before she could finish her sentence Dean had slammed the door shut on her. He could hear her cursing on the other side. He didn't want to give her the satisfaction of opening the door to listen to whatever it was she started talking about again, so he chose to run back up to the balcony that overlooked the front entrance instead.

He made it out just in time to hear Lisa finishing up her speech.

"Maybe if you didn't always push people away, then you wouldn't be so alone! I mean you never shared anything about your past with me. Not once! I'd say there's something pretty messed up if you can't even open up to the woman you've been dating for the past, what was it? Oh right, 2 years!" She was pacing slowly back in forth.

"What does that have to do with anything?" Dean spoke up as he leaned forward on to the railing.

"Well gee, I wonder." Lisa rolled her eyes. "Dean, why can't you just get over this and let me back in? For once will you stop hiding out? This is what you always do! You always freak out over the smallest thing, and when someone tries to get close to you so they can fix it, you push them away! How are we supposed to be together if you don't even give me a chance to work things out?"

"Right, because we can work out you sleeping around like some slut." Dean smiled and nodded his head.

"For crying out loud, what is it that you want from me!" She threw her arms up in the air again.

"I want you to admit that you slept with him!" He yelled. Why was this so difficult for her to understand? "Look me in the eyes and tell me honestly that you didn't sleep with him."

Lisa shook her head in disbelief before looking down at the ground and sighing heavily.

Dean leaned forward a bit more so he could hear her more clearly.

"Alright, alright...I slept with him. Are you happy?" She looked up in time to see Dean storm off the balcony and back into the house.

A few seconds later and he was back at the front door with an even more pissed off expression on his face. "Are you happy? Seriously? That's what you ask your boyfriend after you tell him you've been fucking your assistant behind his back? For God knows how long?"

"You wanted the truth, so I told you the truth! What more do you want?"

"Well for starters I would have liked for you to come to me if you really wanted sex that much instead of turning to the first person to jump in your pants!" Dean ran his hand through his hair and bit his lip.

"Right because we have sex so much. Dean, when was the last time you even thought about sleeping with me?" Lisa's hands were on her hips and Dean couldn't help but scowl even more. Was she really the one trying to be pissed off? She was the one that just confessed to cheating! He was the one that deserved to be angry!

"You know what? Fuck it. I'm done." He turned and stomped angrily back into the house, tearing his arm away from Lisa as she tried to stop him from leaving.

"Dean, wait we can work through this." She pleaded, her attitude changing just enough to sound like she regretted her actions. Just slightly.

"I'll mail you your stuff." He snapped before slamming the door on her face for the final time.

He punched a few more walls on his way back up the stairs. He really needed a shower, and his brother was about to show up any minute.

God he needed a drink.

"Dean? Dean! Earth to Dean, hello?" Dean finally noticed the voice calling him, as well as the hand being waved in front of his face wildly. How long had he been spacing out?

"Huh? What?" His face shot up to look at who'd been talking. Of course, it was his brother, Sam.

"Dude what's up with you? We've been trying to get your attention for ages. Did you like the new ending to the trailer? We added in everything you said to and tweaked the font size and colouring." Sam turned back to the screen on the wall.

Of course after the fight with Lisa, Dean didn't have time to take his much wanted shower due to the early arrival of Sam and Chuck. They both worked with him on the movie trailers, though he was the one that got paid the big bucks since they were all his designs. They'd just recently gone over another cliché trigger happy, action packed, thriller. Movies just weren't made like they used to...though when it came to the previews for movies, he was definitely the first on the calling list.

"Yeah, yeah. It was good, except I think we should go back to the original ending cut. And maybe make the font bigger at the end." He watched as Chuck quickly scribbled down his suggestions on a small notepad. "Oh and maybe change the colour. The white seems too white. Maybe a red since it'll be coming out Christmas Day. I don't know...just something Christmas-y but not too Christmas-y since, well, it's an action movie. But just enough to get people to want to see it during the Holidays, you know." He finished as he pinched the bridge of his nose. A headache was forming, and it wasn't a pretty one.

"Christmas-y but not too Christmas-y, got it!" Chuck mumbled to himself as he finished up his notes. "That's why they pay you the big bucks!" He praised Dean as he turned in his chair to flash him a grin.

"Damn straight!" Dean answered back, trying to sound interested. His mind was still on the fight with Lisa, and God did he want to just erase everything about the past year. He was fine with the good memories with her, but the bad ones...Well who wouldn't want to get rid of the image of their girlfriend boning the geeky assistant? A cold shiver ran down the back of his neck at the thought.

He looked up to see Sam staring at him with his big puppy eyes. 'Great, he knows something's up.' Dean thought to himself. 'Of course he knows, he always knows when something's wrong. He's like got some freaky ESP about these things.'

"What is it Sammy?" Dean finally met his gaze with a tired expression.

"Nothing, nothing at all." Sam lied. "But if there's something you want to talk about..." He offered.

And there it was, little brother Sammy swooping in for another chick flick moment. Dean Winchester did not do heart to hearts. Though it didn't stop him from appreciating his brother's concern for him. He could always count on little Sammy to be there for him...though he wasn't little at all anymore, he'd shot up in height a good half a foot or possibly even a foot above Dean!

Dean sighed heavily and shook his head, "I'm fine. Really...It's just...you know what really pisses me off? This." He motioned around the room with his hands.

"What do you mean?" Sam's eyebrows furrowed and he looked around. "The office?"

"No..well, yes, but not just that. I'm just...Fuck, I don't know. I'm tired of all of this. It's close to the holidays, so we should all just take off for a few weeks and relax! I need some peace and quiet, or whatever it is people go away for." He said as he jumped out of his seat and paced back and forth anxiously.

Sam just stared at him like he was crazy, "Uh, yeah but, Dean, you say that this is our busiest time of the year. Plus, you hate the holidays. When was the last time you had a real Christmas?" He eyed him suspiciously before slowly standing up and leaning against the desk. "Are you sure you're feeling ok?"

"Ok? Yeah...I'm ok. I'm just fucking peachy!" He spat out. Chuck winced in his seat, not sure what to say. "But you know what isn't ok? Me, working. Working! Can you believe it?" Dean laughed and bit his bottom lip. "Because apparently me working a whole bunch isn't allowed, but Lisa! Oh Lisa is allowed 100% freedom from that! It's alright if she stays late every night and, and, fucking sleeps with her assistant! And why? Because I was working too late! What kind of bull is that?" Dean was practically going in circles as he quickened his pacing.

Sam put a hand on Dean's shoulder to stop him, looking at him with his sad puppy eyes again. Dean's whole demeanor hardened as he glared down at the ground. He didn't know why he'd just puked all that onto Sam and Chuck. He didn't do chick flick moments, though, he figured it wasn't so much a heart to heart and more of him dumping his anger onto his friends.

He smirked as he thought about his idea of going on a vacation, "You know if I left I might even read a book. Not just a magazine, but like, an actual book." He chuckled.

Sam couldn't help but snicker, "Seriously? You with a book? I'd pay to see that!"

All three of them burst into laughter at the thought.

Though it didn't change anything that had happened between him and Lisa, Dean smiled at his brother and Chuck for being there for him. Even if he didn't actually share his "feelings" with them.

"Hey man, we got it from here if you did want to space out for a couple of days." Sam patted him on the shoulder and went to pick up his things. Chuck followed suit and began organizing his notes as he jumped out of his seat awkwardly.

"Yeah, I might just have to do that." Dean said to himself.

Just 15 minutes after Sam and Chuck left, Dean had found himself on his computer contemplating the idea of actually finding some place to go to for Christmas. He really could use a get away vacation, someplace new, so he could clear his head.

He flipped back and forth between a few web searches he'd done. He wasn't sure if he wanted to go someplace in the US, or if he wanted to travel outside. He really didn't like flying. In fact he stuck to driving, even if he had to meet up with a company in the country, but out of state.

He'd prefer driving any day.

But something inside him egged him on to find a completely different town. Perhaps a good culture shock would help get him back on the track he wanted with his life.

Dean looked at the many searches that appeared on the screen, "Hmm, vacation rentals. Sounds doable. Disappear for a few weeks? Sounds like my kinda thing." He clicked on the website link.

"Ok, Dean, where would you want to go?" He talked to himself as a list of different countries popped up as well as their respective flags to help identify them more easily. "Right...somewhere that speaks English...Ah, here we go!" He said enthusiastically as he clicked on the flag of England.

Another list loaded on the page, except this one had a whole bunch of different cities. "London...too crowded...Someplace not so touristy...So basically anything else on the list. Awesome." Dean shook his head as he looked at each city. "Well how do I know which one is the best one?" He thumped his head against the desk.

He groaned and looked back up at the screen, clicking on the first town he saw, "Cotswolds...Alright whatcha got to offer Cotswolds. Don't disappoint me." He mumbled. "Barn converted to modern house in the beautiful Cotswolds...Oook, what does it look like?" He clicked on the image to enlarge it and almost fell out of his chair. "Seriously? It looks just like the valley."

Dean quickly hit the back button to choose a different town. He scrolled down a bit more until his curser was far enough away from the last city he'd picked. The next random town it landed on he decided to go along with.

"Surrey. Doesn't sound too bad, but what does it have to offer?" He began to read the description aloud, "Hmm, Christmas in the country. 'An English cottage set in a tranquil country garden.' I could do with some country." Dean agreed as he clicked on the image, he definitely preferred this one over the first, "'Snuggle up by an old stone fireplace and enjoy a cup of cocoa. An enchanting oasis of tranquility'...Sounds girly. But I could definitely use some tranquility."

Dean sat there for a moment before opening up the live chat system set up with the website to connect potential renters to home owners. He really hoped whoever owned the cottage would be awake, he wasn't too sure about the time differences, but he knew if whoever it was didn't act fast, then he'd probably chicken out and spend his Christmas at home. Alone. Again.

Dean: I'm interested in renting your house.

Dean: I'm wondering if your house is available this Christmas, 'cause if it is you could be a real life saver.

Dean: I know it's ridiculously late, but if you're at all interested please contact me.

He sat there waiting for a reply. He knew it was a crazy idea, and somewhere deep down he knew he should've just stayed home, but he didn't want to be stuck in the same place, doing the same routine, except this Christmas alone due to the sudden break up.

Dean leaned back in his seat and propped his legs up on the desk. He stared at the screen for what felt like hours, but he was sure was only a couple of minutes before he finally got a reply.

He sprung forward, he could feel his heartbeat pick up in speed.

Anna: I'm very interested. But the cottage is only really available for home exchange.

"What the hell is home exchange?"

Anna: We switch houses, cars, everything. I haven't done it before but friends of mine have.

"Dude it's like they read my mind."

Anna: Where are you?

Dean: L.A.

"Please say yes. This is the only time I'm actually going to consider doing this..." He crossed his fingers and prayed to no one in particular.

Anna: I've never been there, but always wanted to go. I'm Anna by the way. Very normal... Neat freak. Healthy. Non smoker. Single.

Dean laughed when he read the response. "What is she trying to hook up with me or something? Sorry Anna, but dating's out of the picture for a good while.."

Dean: I'm Dean.

"Loner, loser, and complicated wreck. Goddamn I sound like a chick. I seriously need a vacation."

Anna: Hi.

Dean: Hey.

Dean: Your house looks really awesome. Just what I need.

Anna: Really? Thanks. What does your place look like?

Dean: My place is nice – kinda bigger than yours.

Anna: Not hard to be.

Dean snorted, "No shit. Your's could fit in my garage.."

Dean: Can I ask you one thing?

Anna: Of course.

Dean bit his thumbnail briefly before continuing.

Dean: Are there any women in your town?

Anna: Other than myself? Zero. Everyone else is married.

Dean: Sounds good to me! When can I come?

Anna: Tomorrow too soon?

Dean mulled it over for a moment. He could really go for a nice getaway, and fast.

Dean: Tomorrow's perfect!

Anna: Ok! We are on! 2 weeks starting tomorrow.

Dean closed out of the chat and let a breath out he hadn't realized he'd been holding. "Alright, Winchester. No backing out now. Never shall it be said that Dean Winchester didn't willingly get on a plane for a trip out of the country!" He quickly booked a ticket so he wouldn't have to worry about missing the flight over.

He got up and started gathering some clothes to take with. He wasn't sure what he'd need, or what the weather would be like. He was used to hot and sunny for Christmas. "What the hell, I'll bring one of everything just in case."

Dean packed the rest of his suitcase and put together his travel documents so he'd be ready to go come morning. "Good thing Sammy talked me into getting my passport last summer..."

It was late in the afternoon and so he figured his shower was long overdue. When he walked back to his dresser, he looked up and saw one of the many pictures of him and Lisa. He stared at it and felt his stomach churn at the sight.

"Definitely need to get rid of these. Time for something new." He gathered up all of the pictures littered about the room and tossed them in the trash.

Suddenly the flight to Surrey couldn't come fast enough.