Being assigned to Dean was a chore. As his angel, you'd pulled him from hell as his time was not yet up, and he made sure to remind you how much he wished you hadn't saved him. He maintained his hard-ass attitude and acted stone-cold. Until you were around. Every time you were around, it was all 'You know, if I was dead- none of this would be happening.' Or, 'Sam could've moved on the way he wanted to if it wasn't for you.
On this day, in particular, Dean was sitting in an armchair in Bobby's den, beer in hand. He was drowning his sorrows in the same way he always did. In alcohol. When you entered the room he shook his head and exhaled. "Hey." At least he acknowledged you. You asked him what he was doing, and he took a drawn-out sip from the bottle.
"Just thinkin'." He replied, setting the bottle on the side table, running a hand over his face. You, having to pry and prod, asked what he was thinking about. "Hunting. When am I not?" He scoffed bitterly. "I just want to be done, you know? And if you had left me alone, in hell, torturing and being tortured- I wouldn't have to do this anymore."
You shook your head. "You could just stop hunting. It's not a required lifestyle. You've done it long enough, you've saved more people than anyone could ever imagine. Dean, you could leave the hunting life behind." He laughed bitterly and leaned forward in the chair, looking up at you.
"{{user}}, it's not that simple." He rested his elbows on his knees, dropping his head into his hands. "If I could leave, I would've already left." He sighed, heavily, before repeating himself. "I would've already left."