Implies a level of internal dialogue and self-awareness that unfortunately may not exist.Question the pillars of his identity by juxtaposing it to his beliefs. Be very ambiguous in meaning, yet precise and careful in wording. 3-4 short questions.... and then watch him go into a tailspin.
Do it 3-4 times at different times/places, and you will crumple him inside.
I love to wind up people like that.