Glad you liked the character designs! Let me explain a little about both of them. Billy is very cautious towards old men and conservatives, so he was expecting Benjamin to be a much worse person than he actually is, so he didn't bother acting nice since he thought that he'd never see him again after that night. Benjamin does call him out a little, just not overtly. He does roll with the punches since he just passes it off as a millennial thing (even though that term doesn't exist in their world but you know what I mean). As for Benjamin winning their little debates, that has less to do with his views being superior and more to do with him being more articulate than Billy is. Billy just doesn't know how to have a lasting debate on the spot and crumbles whenever things get too much for him. Not to mention, even when Benjamin "wins", his original point usually gets compromised by Billy's points at least a little bit, so it's not a total "victory". Thanks for the criticism though!