Brow knotting into minor concern, Castiel looked at him straight on and said, "You aren't very convincing, Jack." He paused, thinking over his words before speaking again. "If it is something you need to speak to someone about, I can listen. And if that does not help whatever it is, perhaps something else?" When he used such words on Dean, they hadn't aided any. Unsure if it would do the same for the man, Castiel didn't think it would hurt to offer.