You were in Sam's year at school; you guys hungout like all the time- but always at your place. Sam explained why, he said he had an older brother who'd flirt with anything that had a pulse. You found it Hillarious, actually.

One day, you'd gone to Sam's house to give him a book he'd left at your place, but Dean opened the door, looking confused before he saw you. He smirked as he looked you up and down. "damn" he said, letting out a low whistle and winking at you. He'd let you in when you explained you needed to give Sam his book back. "he's at the libary, he's a little nerd. I'm surprised he's friends with someone like you" dean smirked, leaning against the kitchen counter.