This is a Jimmy Novak appreciation post.
Okay can I just bring attention to the last gif? At this point Castiel is using Jimmy’s daughter as a vessel and he does one of the most comforting, human gestures; he runs his hand through his hair. This is Castiel, an angel that doesn’t understand references or gestures and can only just about handle “normal” communication and as Jimmy is dying, he runs a hand through his hair. I really think Castiel grew attached to Jimmy while using him as a vessel, because I don’t think we’ve ever seen Castiel do something so earnest in an attempt to comfort.