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Dean knew what the other kids' mothers thought of him whenever they came to pick his friends up. Oh, it's that Winchester boy again, he knew they thought. Probably off to create trouble. Just look at his clothes. His father is probably a drunkard.
It annoyed him to no end, getting the same looks from the women. They didn't know him, so who were they to judge?
Then, there was him.
Dean was walking and laughing with his friends again, walking down the steps, when one of his friend's brother came to pick him up. Dean expected to get the same dirty look, the same what are you doing with my son?! looks, and was pleasantly surprised.
For the brother looked at him, and saw something different. Instead of the dirty looks he got, the brother smiled instead, and stuck his hand out, "Hello there, my name is Sam. I see you're a friend of my brother's. Hope to see you at the house one day, yeah?"
Flabbergasted, Dean just shook the bro-Sam's hand and watched as the man walked away with one of his friends.
He made sure from then on to hang around that friend only, so as to get glimpses of the man and his smile. He knew it was selfish, and he barely even knew his friend, but Sam was a one of a kind person, and Dean knew that he wanted to be around him more than anything.
It was like this until a couple of months later, when Sam decided to seek Dean out.
That was when Dean finally got to have a true friend.