His expression tilts pleased again, and he has the semi-conscious realization he doesn't feel any pressure to be doing anything more than chatting on this sidewalk, a good sign for proto-friendships. Caleb is the kind of person satisfied by exactly this sort of idle socialization; he's had girlfriends who feel at loose ends if not constantly engaged in something like dancing at a club, or dinner, or ...say, a screaming match, but just talking tends to do it for him even if he has no objection to any of those other things.
....sans the screaming matches, but those seem to invariably go on anyway. Meanwhile: "Some people are okay when you ask 'em potentially personal questions, some aren't." He shrugs, comfortably, as all such gestures seem to be on him. "But since we're here--what about it? Would you say you're not nice? 'cause it sounds like a tragic misinterpretation to me."