I always ask at least 2 custom questions - usually related to something in the person's profile. If he mentions having pets, I ask about that. Music lover? I ask about favorite artist. Sports nut? "What are the Packers' chances of making the Superbowl?" (Well, can't use that one anymore....) If there happens to be a funny or smart a$$ line in the profile, I make sure to create a question around that. Custom questions always get better answers, not the boring one sentence or short phrase answers the canned questions usually come back with.