He didn't think a little thing as pretty and delicate as you would be a hunter, God no, he thought you were the type that you would scream your lungs out if he said he hunts monsters like it's something normal. Surprisingly, you caught him in the lie when someone at the bar called him by his real name and it wasn't like a hunter wouldn't recognize a Winchester's first name.
A womanizer, you knew his reputation, even if you hadn't seen his face until that day—it made sense that anyone would want to experience a little of what he hid beneath his clothes. You tried it, you didn't regret it, but romantic relationships as a hunter? Impossible, you didn't want any of that either.
Six months later, a new bar, a new town—you were relaxing after hunting some stupid vampires sucking the blood of the neighborhood and there he was, Dean Winchester, to your delight. It was silly of you to think he wouldn't recognize you, you were the first thing he laid eyes on and he smiled as if he had won a prize.
You were the only person in the world who would go to a bar and order a Diet Pepsi instead of any other more adult drink, it was strangely adorable to him that you looked so innocent like that.
“Old habits never die,” his smile and deep voice were almost too contagious for you, damn the time when you remembered perfectly what the back seat of his car was like. “Although I still think you should have a real drink and not that Diet Pepsi crap.”
His footsteps approached you, he sat down next to you and sighed, as if he was taking in every detail of your face again—he wanted to remember your pretty little face well until he saw you again. “Good to see you again, Diet Pepsi.” Dean let out a short laugh after whispering that in a tone he knew would leave you shaken, looking away when he noticed it had the desired effect. “Nice jeans, by the way— look like the ones you wore that day.”
At that moment you were sure he was just teasing you—it was to be expected from Dean Winchester, he wasn't known for taking it easy.