Dean Winchester

thewrittenfae

Dean has been trained, from more or less age 5, how to hunt and survive in a world filled with all sorts of magical creatures. He's a master marksman with guns, he's highly skilled with knives and blades, a master hand-to-hand combatant. Behind his smarmy smile, he's also incredibly intelligent and a good tactician, strategist and survivalist. Because Hunters can't exactly go to the hospital all the time for their wounds, he's also a skilled in medical knowledge. He's a mechanic, keeping Baby (his car) running and fixing it when needed. And he also is an adept cook.

Family is everything to Dean. Because of how he and Sammy were raised, aware of all things manner of trying to kill people, and only ever fully able to rely on those two people, he puts unwavering stock in both his father and his brother. And this does extend to found family. Once Dean considers you family, that's it. You're in with him, and he'll go to Hell for those he's loyal to. Literally.

Under all his smirks and teasing comments, Dean actually has an incredible heart. Despite his firm belief that all monsters are bad, because of circumstances allowing him to get to know a few of them, he's had harder times handling them. In some cases not even able to take the kill, or letting people make a case for why they're not the monsters he thinks they are. Occasionally this has bit him in the ass, but at the same time, it shows his softer side. He while he tries to hide it or pretends to actively not care with some smartass remark, his heart is shown in the way that he carries the weight of those he wasn't able to save on his shoulders, letting it shape new decisions at times.

Dean’s determination to do the right thing, to him, is a strength. He has been raised, and thinks that he’s hunting the monsters for the greater good. To keep people safe, because he and his father couldn’t keep their own family safe. Specifically his mother. In the end, he’s trying to help, to be the white knight, the hero. Even if he’s more the ambiguous gray hero in reality.

Dean can be extremely stubborn to a fault. This is incredibly damaging when he thinks that he's right, and won't listen to others who are trying to tell him that he's wrong. And it's usually only when he's had his ass handed to him, rather painfully, that he'll bend and stop being so stubborn. It also leads to him, in a personal way, being a fairly slow learning as a whole too.

He has on occasion, been known to be too cocky and it's gotten him into trouble. Thinking because he's been doing something for so long, most of his life, that he knows everything there is about the things he knows. It's dangerous and has been known to occasionally, almost, get someone killed because of it. Sam’s had to rein him in a little and make him sit down, trying to get him to listen. It’s a really hard job.

Family is also his weakness, because they mean everything to him Dean can be brought to his knees if someone threatened them. Also kind of a little feral puppy to save them It's the best way to get to him, and it means that if one of them turns against him, it means that he can't do what's needed because they're family. We've seen this when a demon took over his father, Dean couldn't kill him despite John telling him to when he was able to repress the demon. In later episodes, we're also shown this when Sammy is taken over by Lucifer, and even when Dean is confronted by his Amazon daughter who'd been sent to kill him - Even with her trying to kill him he couldn't hurt her and Sammy had to kill her instead.

Because of what he hunts, and coming into this he won't know if his father and Sammy are alive after the accident, and this being season one Dean who hasn't been through as much shit as Season 16 Dean, most of his nightmares revolve around either ending up one of those monsters - vampire, werewolf, demon - and hurting, eating and killing people. Or finding his father, only to find out he's been turned into a monster and has in turn decided to hunt Dean and Sammy. Or also of finding out that they passed while he was here.