1. How does your character think of their father? What do they hate and love about him? What influence - literal or imagined - did the father have?
dean’s relationship with his father is a layered one. it would be incorrect to say it was good, and equally so to call it bad. when dean RECALLS his father’s memory, it is with mixed reaction – occasionally he dwells on the moments where john ruffled his hair, where he grinned at him for a well-timed joke or a successful hunt. it is likely to imagine dean holds his memories of john as a loving man so carefully because through his childhood, they were few and far between.
john has indoctrinated dean with many unshakable ideas. the effects are not always negative – dean would associate his disbelief in giving up and his fighting spirit to the teachings of his father, but also the codependency shared with his brother and the desperation to protect, protect, protect. he allows guilt to wrap around his heart and self-loathing to stare back at him in the mirror every morning, and it all stems from the need he feels to be someone john can be proud of. he is a leather jacket, a box of cassettes, and a car that creaks with every opening of a door.
at least, he was. the world john winchester gave his son is not the world dean can see, not anymore.
2. Their mother? How do they think of her? What do they hate? Love? What influence - literal or imagined - did the mother have?
when dean thinks of his mother, it is with reverence and beauty and a light that cannot go out. he was too young to remember much, but the memories he DOES have are of a woman who shone with the unfailing love she gave her sons. mary was a treasure in this world – and perhaps some of these opinions are merely relaying what dean has heard his father say in the past, but he remains doubtless that they are true. she is a guide when times grow dark. she alone could pull john from the depths of depression and push him to his feet, ready to teach his boys how to fight and who they are fighting for.
6. Did they feel rejection or affection as a child?
this has been somewhat covered by the previous questions, and it is again not a simple answer … yes, no, yes again and a hell no just to add effect.
once his mother died, the affection john COULD have offered dean shriveled up into a fixation on killing azazel and nightmares visited when the clock is pointing towards early hours. affection was rare and priceless, usually from when dean obeyed thoughtlessly and watched over his brother unblinkingly. he did what was necessary, but sam took most of the praise. wonder child.
as dean grew older, and sam grew older, and john grew exhausted, the rare- offered affection grew absent. rejection wasn’t the product, but an iron heart and bit-back tears became the norm. john didn’t speak when he was proud, but he did when disappointed.
dean learned that sam was important, and he was not. perhaps that could be considered rejection. perhaps it was just the endurance of hardship regarding the living shadows they all knew were there.
8. How does your character feel about religion?
take him to an altar, and he’ll make sure to punch a hole through it.
religion is a fallacy. dean has stood before angels and archangels and spoken with the tiny gods that populate the minds of thousands. he has expected awe, fear, terror – and he has received a laughing stock in return.
there is only one who has ever given him an ounce of faith in his past, and it is a string he cannot cling to. with castiel he prayed and he tried and he looked desperation in the eye and told the heavens he needed them, and with castiel he spat in god’s eye.
the only angel he ever grew to trust – the only creature to ever give dean hope in the form of clasped hands – and dean pulled him from the pedestal he stood on long ago. what does it mean to dean that his strongest link to actual faith fell from grace with a curse on his tongue and tears of betrayal in his eyes? no, that does not give a man reason to believe in anything. what does it mean that dean has looked the gardener in the eye and joshua has told him god is not interested anymore, only to have the lord reach down and pull his fallen angel up from the dirt once again?
what does it mean to know that there is a god, and there is a heaven, and jesus christ himself was not the stuff of myth and legend, only to find out that such a revelation is as far from miraculous as something can get? well, it does stuff to a guy’s head.
9. What about political beliefs?
it is a vague phrase, and for a tired man it will offer distorted answers. no, dean is neither left wing or right wing, capitalist or socialist, democrat or republican. if someone asked him his opinion of george w. bush he would shrug briefly and turn the conversation around. would mitt romney have done better than barack obama? he doesn’t know, and he doesn’t care. dean’s so far off the grid that the law of murder could change and he wouldn’t really notice – the winchesters do things their own way, and very little stands in their path. especially when they’re respectively dead.
ask him about his political beliefs, and he will tell you that crowley is preferable to abaddon, but no king of hell will ever be a good and just ruler. he will speak of commander castiel with absurd fondness, the righteous angel that deserves a throne in heaven more than any other angel or archangel he’s met in his life – the one that proved his GOODNESS by dropping his entire army off at the door step of a war he could not win, only to save and not sacrifice a friend. those are the kinds of politics he looks towards: contracts between angels and demons, a god in a man who thinks he can rule the world, the dicktator ejecting his disloyal family from their home in heaven. these are the politics he understands.