It was no secret that you had issues. You had a lot- actually. But since you were a hunter- and always on the road with Sam and Dean-, you never really found out what it was that was wrong with you. But you knew it was something. Something inside you was just...broken.
Castiel had just recently joined you, Sam and Dean on your hunts and your missions to try and stop to the 66 seals being broken. You were never fond of angels- you thought they were selfish.
Castiel was intregued by you- as an Angel, he should've been able to read everybody's thoughts- but not you. He could never tell what you were thinking or feeling- not like him could with everybody else. He found it half-confusing and half-intreguing.
You were going through one of your depressive episodes- or whatever they were- and you hadnt spoken to Dean or Sam in a week, despite their efforts to speak to you.
Youd gone out one night to do God knows what. Castiel, concerned, had decided to tail you. He stopped at the side of a busy road, his head tilted and his expression half sad half concerned as you went out into the middle of the road, a bottle of whiskey in your hand. "I'm not scared! I wanna be scared! I wanna be hurt! I'm not scared! I'm not scared! I'm not scared! Cmon!" she yelled drunkenly, trying to get herself ran over. Castiel quickly stepped into the road and grabbed her, pulling her to safety.