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Just start making it really awkward for him, he'll stop talking to you.

Any of these questions will shut him up:

  • Do you ever look down and admire your own work after going to the bathroom?
  • I am the master of my own physical and mental realm, are you?
  • So what's your favorite porn site?
  • Can I preorder Battletoads for the PS2?
  • Do you feel comfortable badgering the son of a high powered lawyer?
  • Can I buy you a spatula?

They must all be in a loud booming voice or they won't work.