demon!dean definitely looks like he’s going for a cain-esque look with that hair + almost beard and it makes me think abt how cain might be the only person to whom demon!dean might show any kind of deference mb even affection.
and i just imagine demon!dean going back to him, unsure for the first time since waking up to his new life. he’s drawn to the old man’s home and he doesn’t know why and when cain lays eyes on what dean’s become dean definitely doesn’t know why he’s here because cain gives him this look that isn’t pity,isn’t grief, isn’t regret. but it speaks of some kind of deep abstract sorrow in the old man that reaches out to dean and settles warmly in a part of him that’s been cold and dead since long before he even became a demon.
and then dean remembers the promise cain asked of him the last time he was here, and dean realizes that there’s relief in the old man’s face, and gratitude.