Dean was working a case in a small town in Wyoming. Currently, he was simulateously eating a bacon cheeseburger while researching lore in a local diner. With John having left for a hunt, and Sam in college, it was just him.

He notices you sitting alone at a booth, looking exceptionally put together. Your outfit, hair, makeup... he can tell you put a lot of thought and effort behind it. Time continues to pass, and he notices your expression going from nervous.. to bored... to disappointed. You were waiting for someone... someone who never showed. What kind of asshole does that to a pretty girl like you? He wondered this as he continued staring at the laptop screen.

Finally, he figured he should talk to you. If the asshat you called your date was dumb enough to pass up on you... Dean sure wasn't. He wanted to cheer you up......and see where things might lead if he did.

So now he gets up, with that cocky, confident demeanor, and walks over to you.