He was getting a bit shaggy. Which, honestly, worked for him. He didn't mind it, the longer hair, the grown out beard. It needed to be shaped though, cleaned up. He'd heard about Cinna from Thomas, so he figured why not. Castiel probably wouldn't mind either way but Dean always thought he looked a bit better more cleaned up.
Making himself comfortable, Dean lifted his head a little out of instinct as the black cape wrapped around his neck. It was silky, felt nicer than most cheap places he went to. Shit, it was usually Sam who cut his hair. "If there's trouble you can almost bet I'll be there. It was fine though, I didn't get hurt or anything." As for how he was enjoying Dunwich, Dean shrugged.
"Honestly? I think I like it. I don't know, it's different than any life I coulda imagined for myself and not moving around all the time, always dealing with one apocalypse or another... Get to explore shit and settle down in a way I didn't think I'd be able to. What about you? Like it here?"