Personality: Dean tends to come off as impulsive, sarcastic, and shallow. In reality, he is a bit of all of those, but they are also a cover for deeper feelings that he would rather not allow others to see. He loves to play practical jokes, especially on Sam, and he often jokes around on the job as well, picking rock star names as his and Sam’s aliases. Also, there’s always time to stop and flirt with pretty girls, even if he is on the job.
He’s quick with sarcastic comebacks as well, and he doesn’t care who he’s talking to. He always has something mouthy to say to the police whenever they bring him into custody. A lot of this particular attitude seems to come from the fact that Dean protects people every day from things that the authorities have no idea even exist. These people know nothing about Dean’s world, and he knows nothing about anything that they’ve done, so he has very little respect for them.
Dean has spent most of his life following orders from his father, with the top priority being his younger brother Sam. Even as his dad knew that his own life was coming to an end, he reminds Dean to look after his baby brother. Because of this, Dean places a very high value on looking after Sam, making it his sort of mission in life. Obviously, even from a young age, Dean has had trouble forming real, long lasting emotional ties with anyone, and that just makes him more attached to his family. Often, if something happens to Sam or he starts to do morally questionable things Dean takes it as a personal failure on his behalf. He even goes so far as to sacrifice himself for Sam, believing that he can’t go on with his brother dead.
He also hides a deep insecurity. Although he loves and cherishes both his father and his brother, he’s always believed that Sam was their father’s favorite and Dean was just a tool that could be used to help protect him and to be trained into the perfect soldier. These thoughts don’t do anything to lessen Dean’s love for his family; they just cause him to view himself as more disposable and less worthy than them.
In some ways Dean’s moral compass is a little shaky. He has absolutely no problem with credit card fraud, impersonating a member of the FBI, CIA, or any other government agency, or digging up graves in order to salt and burn some nasty spirit’s bones. He does, however, hold a great deal of issue with Sam’s use of his abilities. While it’s clear that Sam mainly wants to use his abilities to do good, Dean sees them as something dangerous and unknown.
Dean’s not great with dealing in unknown or faith-based things. His personal motto is that if he can see it, touch it, and fight it, it’s real. Otherwise it had might as well be Santa Claus.
Although Dean has shown scorn towards living a “normal” life or Sam wanting to be “normal”, he secretly wishes that he could be “normal” as well. Dean never seemed to resent hunting in the way that Sam did, but he expressed resentment over Sam’s being able to have a normal life at college while Dean continued the hunt. Also, a djinn once granted his wish to have a normal life, sticking Dean into a dream world where his mother had never died. While he loved the feeling of the dream, a reality where he and Sam were strangers to each other, and all of the people that he’d saved as a hunter were now dead wasn’t something that Dean could live with.
Dean has a lot of guilt issues and if he has to take a personal hit in order to feel better about something, he’s more than willing.
History:
http://supernaturalwiki.com/index.php?title=Dean_Winchester Strengths: Dean doesn’t really have any special abilities but he has quite a few talents. He’s good at fighting and is skilled with several different types of firearm, as well as quite a few melee weapons. When it comes to combat Dean’s very resourceful and is usually able to use his environment to his benefit. After all, he was trained to fight things that go bump in the night from a very young age, and his father was very thorough in his training.
Weaknesses: His brother, first and foremost. Sam’s the only family that Dean has left, and Dean loves his brother more than anything despite their occasional falling outs. He would also do anything for him, including sacrificing himself, which he has done in the past. Dean also has a soft spot for Bobby since he’s been like a second father to the Winchester boys.
Dean is also terrified of flying, claiming that as the reason he drives everywhere.
Preferred drop-in point: Truth or Consequences, New Mexico
What are some of your plans for this character in their new environment? Dean is going to do what he does best. Which means he’s going to be making rounds - occasionally pretending to be FBI, police, or a religious figure in order to get people to trust him - and he’ll be asking questions. He’s going to be certain, at least at first, that this must be some sort of supernatural occurrence. Or, at the very least, that it’s probably the fault of a supernatural being. So he’ll get his information, try to team up with Castiel again, and hope that he’ll be able to get out of this world in time to find Sam.
Third Person Sample: “Dammit!” Dean chucked one of the old cell phones at the screen as it flickered out. Another dimension? More like “Back to the Future Part 4”. And to top it all off, there was no “Doc” in sight, much less a magical, time traveling car.
He looked back at the glass tube that he’d been crammed through. Well, that looked un-fucking-promising. Things were never that fucking easy. Dean walked over to it anyway, giving the thing a good kick when nothing happened. It didn’t really make him feel any better though.
Grumbling to himself, Dean stalked over to the cardboard boxes, raiding them for clothing and grabbing a few cell phones as well. After a moment’s consideration, he dumped out an entire box and put his stuff into it. Things would be a lot easier to carry like this. He looked around the dimly lit room. “Well. Guess there’s only one way to go from here.” He picked up the box and started walking, blinking as he finally emerged into the bright sunlight… in the desert.
“I bet you think this is really funny!” He shouted at no one in particular. Okay maybe that comment was directed at Zachariah, the “Biff” of his situation. Or something. It made sense, okay.
Anyway. Now Dean was really irritated, and Zachariah hadn’t even bothered to rear his ugly head yet. Not that the guy ever had really stellar timing.
Dean sighed, and had started moving through the town - city? - when he caught site of a familiar… wait a minute. He froze, his hand moving towards where he’d hidden Ruby’s knife on himself as he became painfully aware of just how vulnerable he was out here. So maybe just strolling on into town hadn’t been the brightest idea. But he was here now and that motherfucker was the Trickster.
Ha! Alternate universe, my ass. So you’re behind this.
He slowly approached the other man - if he could even really be called that - his hand never straying far from the knife. It might not do him much good against the Trickster (hadn’t they killed the stupid thing twice now) but it was comforting.
There was a moment as he was closing in where Dean briefly considered just stabbing the son of a bitch, and damn it all to hell if anyone saw him. It wasn’t like these people were real anyway.
Dean had nearly gotten close enough to do…something (he wasn’t really sure what exactly. He was kind of playing this by ear) when he saw the Trickster’s companion.
“Dude. Cas? What the fuck is going on around here?!”