Just a few of what i guess you could call my own Dean head canons. I read a friend of mines, and decided to do a few of my own, from various times in his life. Most ( if not all) are about his and Sams relationship ( not wincest - just close brotherly adorableness!)
When Sam and Dean were teenagers, Dean dreaded the day Sam would get his first real girlfriend. It would be like he wasn't most important anymore.
Dean didn't like lying to their father, but if it meant protecting Sam, he would. A few white lies really wouldn't make a difference with all the other stuff they did.
All of his best memories from his childhood involve Sam in some way.
When Sam got into his first fight and came home with a black eye, Dean had to threaten the names out of him. The four boys were out " Sick" for three weeks. Teach them to mess with a Winchester.
When Sam got sick, Dean was almost happy. It meant less training, and he got to sit in bed with Sam and watch re-runs and bad movies. They got to be real brothers for a while, not soldiers.
When Sam and dad used to fight, he couldn't believe neither of them knew why. Sam had inherited all the stubbornness from their father, and the pride too. More often than not, they were fighting with the Same idea in mind, but neither one would give in. They were to similar for their own good.
Dean lets Sam take all the credit for being the clever one, but he's a lot brighter than he lets people know. He just thinks it's easier to do what they do without flaunting his brain power.
Dean was the one who gave Sam his first beer. Sam was sixteen, and their dad was away for a couple days.
Dean was also the one to have " The talk" with Sam. It would have been worse for the kid if their dad had to do it, but Sam still couldn't look him in the eye for a week afterwards.
Dean taught Sam to drive in the impala, then took him to get the one true piece of identification he would get. It Thought Sam had earned getting the license in his own name. The first time he drove without Dean was a twenty minute trip to the diner. Dean couldn't sit still the entire time.
No matter how often they fought, Dean regrets pretty much everything he's ever said to Sam when he's angry.
Sometimes he envies Sam for not knowing their mother. It means he doesn't have anything to miss. But then he thinks how bad it would be to have nothing to remember about someone so important, and he hates himself for thinking it in the first place.
He knows he can be an crappy brother sometimes, but he would still die for his little brother in a heartbeat.
He makes fun of Sam for it, but he's always been jealous of his height advantage. He's oldest, he shouldn't have to go on his toes to look Sam in the eyes.
When he's having really bad days, there's one thing that keeps him going. After Dad died, after Ellen and Jo. The thing is, if they hadn't been raised in this life, him and Sam probably wouldn't be this close. No matter all the horrific, traumatising hell they go through, it's him and Sam. To the end. And honestly, he wouldn't have it any other way.
Even now, when he looks at Sam he can still see his sixteen year old brother in those eyes. And he knows that its just the built up, hard exterior that blocks him out. But he keeps fighting for him. Just for those few times he see's Sam really laugh when their talking, or some soft sarcastic comment about the music he likes. That's his Sammy.
It was selfish, but when Jess died, he didn't know how he was going to get through it. The pain in Sams eyes, the nightmares that he still occasionally gets. He couldn't imagine the pain of seeing someone he loved die like that. It was like a piece of his brother died, and that killed him too.
Damn Sam, but Bon Jovi is starting to grow on him. But only the good ones. None of that pansy stuff.
For weeks after cold oak, he would wake up in the middle of the night panicking until he saw Sam lying in the other bed. He would sit there for a little while, watching him. And he never once regretted taking the Deal. It really was the only option.
He never really liked black coffee, he just drinks it cause the smell reminds him of their dad.
He thinks they're pretty lucky not to have some serious damage by now. Lost limbs, wheel chair or worse. Hell, they're pretty far from perfect, but he has no idea how they survived this long. He never expected to.
He might have stopped outwardly acting like an overprotective soccer mom to Sam long ago, but he still feels exactly the same way. He just has better self control - mostly.
He hasn't forgotten everything Sams done. But he's forgiven most of it. He knows his brother better than anyone, and he wouldn't do anything to hurt him on purpose. It was all good intentions, just really really bad choices. And he can't hold that against him.
He knows Sam might be right about the unhealthy obsession with the impala. But who cares. Other than Sam it's the only real thing he has left. So excuse him for loving it.
It really gets to him when Sam says how much he hates hunting and how they live. He's fine as long as he's got Sam, but now it's like having him isn't enough for his brother.
If he could change one thing about Sam, it would be that he would stop eating that sissy food and eat some real food. Oh, and his music taste. Don't forget the stupid coffee…
When they got the protective tattoos on their chests, Sam would never admit it, but Dean was sure his little brother was scared. That's why he insisted Dean go first. And he had to sit next to Sam while he got his done. And basically crushed his hand when the needle hit a sensitive spot.
Sam doesn't know it, but he reminds Dean so much of their mother so much sometimes. The way he care for everyone else, how he speaks out to protect people. How gentle he can be when someone's in pain. Just the way he is.
Dean made a bucket list a few years back. A real Christmas for Sam, seeing the grand canyon and spending some quality time with a supermodel were some of the first.
The only thing he is truly afraid of is dying alone. Mostly it's of Sammy going before him, or getting separated during a hunt. He isn't afraid of dying, just of not having anyone there for his last seconds.
No matter how much he'd like it, he really can't imagine settling down with anyone. Its always been him and Sam, and he's never found anyone outside the hunting community that understood.
Dean's always wanted a dog. One of those big, black German Shepherd's. Or maybe a lab. It'd be awesome to have a dog to take hunting with them.
When their father died, Dean lashed out to Deal with it. Emotionally to Sam, physically to the car. But at least he dealt. Sam - he just pushed it down. And Dean couldn't work out how to help him. Which made him even angrier.
Sam is the only one that he's let see the real him, apart from maybe his father. Even Lisa didn't know everything. All the little things that make all the difference. Those were reserved for Sam.
Dean still has every single present Sam has ever given him. The hand drawn card he got when Sam was seven, the "D" key chain when he was eleven, and of course, the amulet. Always.
Thanks for reading my ramblings :)