Comment by apazzolini

Maybe ask if he has ever exceeded the speed limit, or run a red light, or failed to signal a turn. All things that could be monitored by a smartphone and reported to the police automatically.

Have him publish his full name, date of birth, social security number, mother's maiden name, bank checking and routing numbers, credit card numbers + expiration dates + cvv numbers, nude photos of his wife, nude photos of himself, all of the search history from all of his browsers online, all visible to the public.

Surely he doesn't see any point in keeping any of that information private, he's a good guy and not doing anything wrong, therefore he has nothing to hide and no use for privacy.