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Like most terrible things in the world, this is Gabriel’s fault.
And maybe Eileen’s, and Sam’s. Fact is, Charlie’s getting married. Which of course Dean would be over the moon about, despite his objection to all things romantic—but this means spending a week with his least favorite person on the planet, his sparring partner in crime, Castiel, both of them united in only one thing—their scorn for love.
So when Gabriel has the bright idea of getting the two anti-lovebirds together, the whole gang is in on the idea. But as the week progresses and things get more and more complicated, they realize that perhaps not all is fair in love and war.
A Shakespeare AU starring Dean and Cas.
When one of his first hunts after becoming human again ends in injury, Castiel is faced with the helplessness of his mortality. Through it all Dean is a constant presence at his side, ever the attentive caregiver, which only serves to increase the tension growing between them.
Despite their age gap and differing social circles, Castiel has struck up a warm friendship with Mary Winchester, a wealthy widowed socialite. When Castiel needs a place to stay, Mary invites him into her house, where there’s loads of spare room. Castiel’s aware that they make an odd pair, but he doesn’t fully realize how things look to outsiders, especially to Mary’s eldest son. All Dean Winchester sees is that his mom has apparently hooked up with a hot young guy (who is totally Dean’s type) and that makes things… weird.
Dean Winchester is in love with his best friend, a man he has never met, who goes by the handle AngelofThursday. Problem is, Thursday values his privacy and refuses to meet. Dean buries himself in his work at his bakery Slice of Pi and in computer games, desperately trying to move on from a man he can never have. James Novak has problems of his own. Trying to cling onto what sense of security he can, he drifts around the city from café to coffee-shop to bar, using their wi-fi to keep his online footprint anonymous. He falls in lust with The Beautiful Man at his favourite coffee-shop, Study/Break, and turns to his best friend The_Michaelsword for advice. A two-person love triangle for the digital age.
Castiel Novak has a love-hate relationship with the Cherryvale Small Business Owner's Association. He's already gained new clients since becoming a member, and made many valuable connections. Cherryvale isn't a big city by any means, nothing like Chicago. Still, it's not exactly small town America, either. Being the new owner of an accounting services firm requires that he reach out to the local business community. Since Cas is an Introvert with a capital 'I', networking is high up on his list of things he detests. Still, he wants Novak Professional Accounting and Tax Services to be the first name other people think of when they need help with their books or taxes. The CSBOA seemed like the easiest and best way to accomplish that, so he started attending, and the organization has met all of his expectations. So he has nothing but a healthy respect and appreciation for the Association itself. His love/hate relationship is with his fellow members of the Association – namely one Dean Winchester, owner and operator of Winchester Automotive Repair and Restoration.
It starts with a prank war and a chance meeting at the auto shop Dean works at. (Based off of Almaasi's prompt: Castiel records audio pornography. Not professionally, or anything - he writes it and then reads it out, and uploads it free to the world. It’s not Dean’s usual type of porn - at all - but there’s something about Castiel’s gravelly, yet somehow smooth and beautiful voice that keeps him hooked.)
Castiel Shurley and his best friend Dorothy Baum have decided to move in together. After his aunt assumes they are dating, she offers them money for the house, but only if they apply for a famous reality show ‘Dream House’. Since they could use the money and he doesn’t want to come out to his aunt, Castiel and Dorothy agree to fake date for the show. But things go wrong when Dorothy falls in love with the show’s producer and Castiel starts to develop feelings for one of the hosts.
Dean Winchester is a co-host of ‘Dream House’, along with his brother. Sam, being a realtor, finds a fixer-upper and Dean turns it into a perfect house for their clients. Even though he has what most people only dream about, Dean is incredibly lonely. He had bad experiences with relationships in the past and he doesn’t think he will ever meet anyone who can earn his trust. Until he meets Castiel.
Police Officer Dean Winchester’s younger brother Sam and his best friend Charlie Bradbury have had enough of watching him pine over his best friend, roommate, and partner on the force, Castiel. Especially when it’s so obvious to everyone but the two of them that the feeling is mutual. Subtle hints and encouragement just aren’t cutting it anymore. Now, it’s time to get drastic. It’s time… for Disney.
After a hunt, Cas and Dean get in to an argument in their motel room and someone calls the police for a 'domestic dispute'. Everything goes down hill from there and Sam has to come save the day.
Sam is finally starting to figure out why Dean and Cas are so intense around each other. It makes sense, really. Granted, nothing is going to come of the longing glances and secret pining unless somebody does something. Sam takes it upon himself to do that something. Buy as it turns out, getting Dean and Cas together is more difficult than he imagines. When the case they're working-- a creature straight out of the Lord of the Rings-- reminds him of a good friend, Sam decides to call in the big guns. Charlie shows up to help with operation Destiel.