[Crowley very nearly says something a little mean, but doesn't know Ray well enough to start throwing particular insults around, so he just sneers at him mockingly instead. Because he's a good person.]

If you're gonna go, might as well go on a giant dick.

[This is not now Crowley would like to die, but hey, each to their own.

He arches an eyebrow at the tie; he'd rather spend an hour in a room with Hastur than wear it, but it might not look terrible on Ray.]

Could work with a dark green, with a black shirt? White would make it pop too much.