AN: this was something completely random I came up with while watching Brock Kelly play young Dean.
He saw her the school after Truman High. Some weeks after that blonde cheerleader said she felt sorry for him; and a few others had called him trash. He'd seen this girl before. Across the hall at her locker, in the cafeteria, across the football field as he and Sammy took the backway home to the motel. Come to think of it, he may have seen her at previous schools too but he was so focused on the hunt and his brother, he never paid a second thought.
He realizes he should've asked her name, that he probably did, because really when did a Winchester pass up a pretty girl? But he just can't remember and he let it go. Sammy was the freak who remember details, not that his dork little brother noticed girls yet, of course. Leave it to Sam right?
Anyway, he shook his head as he caught another glimpse of her. Bright red hair pulled into a ponytail, shimering green eyes, baby blue sweater and jeans. She smiled at him and he was just about to say something but she was gone again. He didn't see her for a long time after that; thinks he may have just imagined her. After all, he's a hunter and it gets boring being alone sometimes. With knowing all the strange stuff he does, it wouldn't have been hard to. Or if she was real, this girl probably went off to college somewhere.
When he saw the young girl next, he was surprised. It was right before his crossroads deal came to an end. Pieces of dreams never making sense but always of the same redhead girl from highschool. What was it about her and who was she?
Then it hit Dean Winchester straight in the gut as he walked through the church attic. A timid but sharp woman with bright eyes and long red hair. Said she heard angel voices and the first thing she heard clearly was his ressurection. It was a few nights later, as they lay in the Impala's back seat, he watching her sleep that the hunter realized he had it bad.
He remembered a time when he told Sam,"She said that angels were watching over us but she was wrong. There was nothing protecting her."
Little did Dean know, two years later, when he met this mysterious red haired girl in person that he would be thinking the same thing about her. He had a connection to this strange girl they had to save. And he had been falling in love for the longest time. With Anna Milton. And she was his Mysterious Angel...