Ask him who he thinks is prettier Jessical Alba or Angelina Jolie. That ought to get him going. Then follow that up with who you think is prettier and why. Then ask him what type of women he finds attractive; what type he likes to date...Follow up that question with what characteristics (not physical) in a woman is attractive to him and important in a relationship...I'm assuming this question is because of a romantic interest in a man.

or talk sports.