Wow, you're right, Ron really did come off as a prick. I mean, I don't even think he was that big a prick in canon, and canon Ron disgusted me to no end.
I also don't anyone could be so stupid to think that plan would work. Even girls with not so great self-esteem wouldn't fall for something like that...at least not any I'm aware of. I mean, I know you said bashing, but....wow.