A lot of people don't realize it, but there is a major difference between funny and fun questions. With funny questions, you again have the free reign to go wherever you think the conversation needs to go. If you know the guy is an old school "Three Stooges" fan, then ask him which character he most resembles physically and mentally and why. You can do the same with any modern-day television shows like "Family Guy" or "The Simpsons." When you ask those types of questions, you really never know where the answer you get is going to take the conversation next.
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