I’m kinda curious, what would happen if Dean met Bowman before he was reunited with Sam? Would he shoot first and ask questions later? Or would he still realize that Bowman is a person and attempt to be gentle?
Dean often does shoot first, ask questions later. In this situation, though, Bowman’s a small enough threat that if Dean finds him, he’ll probably just grab the small and bitchy green leafy thing to find out what it is, and they’d end up sassing back and forth for ten years before getting anywhere useful (without Sam or Jacob, there is no one to break the circle of doom those two can get stuck in).
Dean might be a hunter, but he prefers to think through a case when it doesn’t make sense, and considering the worst this leafy green guy did was bite him, it doesn’t look as though he’s out here, slinging magic and turning wolves against campers. They’d have a very awkward relationship, but they might manage it!
Bowman would definitely make things interesting for him. The little guy hides his fears with yet more snark, so it wouldn’t be immediately obvious that he’s freaked out by this human wandering around with guns and huge blasted knives, grabbing the fastest sprite in Wellwood out of the air. Dean would get quite a tirade of sprite swears shouted at him, in between Bowman trying to kick him and bite him.
As soon as he gets out of the jar, he swears he’s gonna bop that giant into submission.