Of course, the smart answer would be to say 'no', whether there's any truth to it or not, so he's not surprised to hear that response. What does surprise him is all the hints around it that tell him Castiel isn't lying. That for his sacrifice his father might really leave him here.

"Well. That's just sad."

Well, that was dickish even of him. He quits in his pacing and runs a paw through the scruff on his head, "I mean-well, no it is sad. If you can't count on family, who the hell can you count on?"

And he's got no love interest, no family. "You at least got some friends?"