Tweaking Chris by exposing him to his own inconsistencies is always great. Normally, when Chris deals with the world, he's constantly wriggling to be correct. If he can get a 1% chance that he might be correct, he'll take it and he'll believe. And I don't think he has any subconscious thought that the truth might be that he's wrong or anything either. I think he's just slow, and doesn't have the brainpower to think about the subject deeply enough to change his beliefs. So he just says fuck it, and takes the convenient belief.
So, (and I think I've used this example before), when Chris gets taken down by cops, he thinks "hey, a cop is just a man, right? and not all men are strong, so there's a chance I can escape!" and he resists unyieldingly until they actually cuff him (or he gets too exhausted to keep trying, either or). Hell, remember that meme, "I can break these cuffs"? Chris might realize that he can't break metal (y'know, transformers might tip him off to that fact), but then again... maybe he doesn't realize it. Heh, basically, I wouldn't count out Chris yelling and trying to break his handcuffs.
So when you actually do get Chris into a situation where, logically, he cannot be right, it's so great. I forget which call it was from (Alec probably knows, because we're always laughing about this), but someone got Chris into a corner, where he cannot be right, and he just says "wait... what???" Like he was so startled by the fact that he might be wrong. It blew his mind. You can almost hear the gears turning in his head. It's pretty great.