I might be speaking ahead of myself (I have only watched 3:08 of this video), but anyway, in order to win that game (if I was talking to a person or a computer) I would ask questions, not based on logic, fact, or reasoning... but feeling. for example "what goes through your mind (or what do you think of) when you see a sunset" I don't think think a computer could give an answer that makes me think "This is a human responding"