It's fascinating to watch Houses of the Holy now. Dean is so Scully here, with contemptuous sauce on top. Just you wait, Dean Winchester. One angel is going to mean a hell of a lot to you later on.
I love later on, too, in whatever episode it is, when he says, "My friend Cas." Dean has so few friends. None, really, unless you count Bobby, and I think the father figure there overshadows any buddy vibe. I don't think he knew Ash long enough to count him as anything more than an ally, and even Ellen and Jo I think fell under some vague heading of family or comrade rather than friend, with its connotation of companion.
And Sam's not his friend. Sam is his everything -- his family, his home, his responsibility, his proudest achievement, but not really his friend, or not very often anyway.
I know he calls him his buddy to Jesse. I'd love if there had been any in show acknowledgement that this is something that not only have we not seen Dean do, but we've seen Dean actually give Sam shit for doing--maintain connections. It's different because Cas is in their life, but still. It's a big deal. It's a chosen bond, and it's not remotely familial.
I think he also tells Zachariah his friend Cas taught him the angel-poofing sigil at some point.
Dirtybadwrong FCM:
demon!John
shapeshifter!Dean
demon!Sam
C ShapeshifterDean
F the demons (just not together)
(demons ain't the M'ing kind)
Yeah, that doesn't really work, does it?
Hmmm.
M shapeshifter Dean. It's a thing. That look he gives the SWAT team at the start of the episode ricochets throughout me. Oh Em Gee. F YED John, and quite regretfully C Meg Sam. Very regretfully.
FCM, Sam only edition!
pilot Sam, with floppy hair and hope for the future
cocky, blood-drinking, BAMF Sam
Sam Wesson
C Sam Wesson, because he just doesn't know. F pilot Sam...he's a freak who's just not showing it. M BAMF Sam, and have massive adventures of the ass-kicking shotgun-toting kind, oh yes.
FCM, eclectic edition:
badass vampire-killing John
Castiel
broken!Dean (post 5.22)
Does badass vampire-killing John say, "C'mere, sweetheart"?
In that case, F&M, and C everybody else.