Both characters seem a little off putting to me. Billy seems really entitled to the old man's affection, and gets away with treating Benjamin really poorly initially without any consequences. I kind of thought that character flaw would be expanded upon to give us something to balance out our displeasure towards Benjamin's less than savory views. But it seems like Benjamin shrugs that off and Billy doesn't really get any consequences for behaving that way. On the other hand, the bear tends to "win" every one of their political arguments, and Billy just gives some sort of "this is why i feel this way" out rather than actually being allowed to make lasting points that stand up to scrutiny. If the intent was to be balanced, I'm not sure it came off that way? To me it felt like the author put a lot more time and thought into constructing Benjamin's viewpoints than he did Billy's.
Regardless, I still think it's a cool concept, and kudos to you for putting it out there for free for us to enjoy. Also both of the characters have very cute designs.
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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!