Ooh, I did try this once, many many drafts ago...only it was too difficult for me back then; I ended up writing myself into a corner. ^^;
I feel like it makes so much sense though...maybe when I start filling in the later parts of the story, I'll give it another try. At least on a small scale.
There's only one protagonist in the story that this villain respects enough to have an actual conversation with, which is what inspired this thread. I finally wrote them talking to each other for the first time, and didn't really like what I came up with... :T
I think it's just difficult to balance their positive and negative feelings...this protag was a friend of the villain's family, and although she's never met him before she feels kind of vaguely responsible for him, like an aunt...but on the other hand, she has a HUGE chip on her shoulder when it comes to child abuse, and probably shouldn't have much patience for all his excuses regarding his treatment of the MC (despite the fact that she knows what's at stake).
Meanwhile, the villain regards this protag almost like a messiah (in the context of this analogy, she was the previous 'box closer') but on the other hand, he has to be able to convince himself that he knows better than her when it comes to handling the current situation (despite the fact that, again, he started it, and she may or may not have already figured that out).
...So yeah, juggling all this ain't easy. o_o;