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When Dean Winchester was younger, his mother told him he had angels watching over him. He believed her with all of his heart, and wasn't afraid of anything. His angels wouldn't let anything bad happen to him or his loved ones. Dean was positively indestructable. Nothing could hurt him.
Dean was on top of the world, until his world came crashing down on him. His mother died before he could even reach the cupboard that housed all of the family's junk food. He carried his brother outside as he watched his house go up in flames. He knew his parents were inside, but he also knew they would be okay. Dean had angels watching over him, and no angel would let anything bad happen to his family.
Even when his father reemerged from the house alone, Dean still held out hope. He knew his mother was okay - she just had to be. When his dad told him what had happened, Dean couldn't help the tears that fell from his eyes, but he still didn't believe it. She was his mom. She had to be okay.
The three of them spent the night in a motel, and that's when he realised what had happened. His mom wasn't there to tuck him in, and to tell him he had angels watching over him. She was always there for him, and he knew nothing would've been able to keep her away.
She was really gone.
Dean cried himself to sleep that night, his little body shaking under the covers with each sob, trying to find any comfort he could in the blankets. He wanted his mommy to tell him everything would be okay, that he had angels watching over him, and to hold him until he fell asleep.
She wasn't there, though. She would never be there for him again.
He knew then that angels weren't watching over him. If they were, he didn't want them. He didn't want any angels who would let his mom die. Then again, what kind of an angel would let someone like her die? Angels couldn't be watching over him. Angels couldn't exist.
By the time Dean fell asleep, he didn't believe in angels anymore.
He didn't believe in angels when his dad taught him how to fight monsters, either. If so many evil things existed in the word, angels couldn't be real. They wouldn't let the monsters hurt people.
Dean took matters into his own hands. He became the best hunter he could possible be. He took everything his father taught him to heart. He tried his all to become the best hunter and the best son in the world. His dad and brother were all he had, so he would give them his all.
He would kill all the monsters, since there were no angels to do it. He would watch after his brother and his father, because he knew no angels would. He wouldn't even complain about not getting to play baseball or have friends like normal kids, because that wasn't what he was supposed to be.
He kept Sammy as sheltered from what he did as he could. Being exactly what everyone needed was hard, and he didn't want his little brother to feel as obligated as he did. He didn't want to put any of that weight on Sam's shoulders.
Of course, Sam eventually became a hunter, too. For a while everything was perfect. Dean didn't need angels when he had his brother and his father. He could kill all the evil and look out for his loved ones for himself.
Things changed, though, and his little brother went off to college. When Dean's dad went missing a while after, Dean once more wished angels were real. For one night, he wished angels were watching over him, and that they would make sure he would be alright, and that his dad would come home. When he woke up the next morning, head pounding and nausea waving over him, he didn't want angels to be real. Drunk, he could get his hopes up. Hungover and alone, he knew the truth.
His dad wasn't back at the motel, and angels didn't exist. All Dean had was his brother and his father, and he would get them back if it was the last thing he did.
By the time Dean's father died, he knew better than to expect anything else. Everyone left him at one point or another. Nobody was looking out for him, and he just needed to look out for himself. There were no angels there to stop John from dying, and there weren't any angels there to stop his Sammy from dying. Dean had to take matters into his own hands, and bring his brother back.
When Dean went to Hell he knew without a shadow of doubt that there were no angels. No angels existed in a world so dark.
Except, they did. One angel even saved him from Hell.
Dean then went from not believing in angels, to wishing they weren't real. Where had they been when they were supposedly "watching over him," as all of his loved ones died?
No, Dean didn't want to believe in angels. Nothing could be cold enough to ignore the plight of the world.
Time passed, though, and Dean got to know one certain angel by the name of Castiel much better. He knew Castiel was supposed to be an angel, but somehow he didn't fit the profile. He wasn't a coldhearted jackass. Castiel actually seemed to care.
He was oblivious, but he cared.
Dean began to live for the days he saw that tan trenchcoat. Just inside of that trenchoat lived the only real friend Dean had ever known.
He knew Castiel had his back, and vice versa. He taught his angel more and more about how humans did things, and Dean learned more and more about Castiel. He learned every little quirk the angel had, from not understanding references to pop culture, to how his favourite time of day was the sunrise, because of how the clouds looked against the sun.
As time passed, Dean wanted to learn more about Castiel. Slowly, he did. Dean learned how Castiel's lips felt against his, and he learned more about Castiel's life. Castiel told Dean tales of what he did in Heaven, and even though he was lost on what Cas was talking about most of the time, there was nothing quite like listening to Castiel's voice as he spoke of his home.
Dean learned more about love, too, as he and his angel slowly fell in love. He was happier than he had ever been in his life, especially because he knew he wasn't going to let anyone end what he had. His angel watched over him, and he watched over his angel. They wouldn't let anything hurt each other.
Dean Winchester didn't believe in angels. Dean Winchester believed in his angel.