Okay… What is the context here, because if I were Sam I would think it was Deans way of telling him they had sex. Pillow talk.
This is absolutely hilarious and by hilarious I mean asdfghjkl because the scene just went ‘Cas enters room, they talk, Dean gets out of room, Cas lingers inside and looks at room, then scene cuts’ implying Cas gets the Colt there and then leaves while Dean can’t see him, they only needed to say that the Colt was in Dean’t room, like, ‘I keep it on my nightstand’ which would probably even make more sense, but no, under the pillow, knowing exactly the kind of mental connection one makes with the idea of a pillow, what is subtlety and who forgot to put it on the show’s budget *chases Berens and beats him with a stick*