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What do you do when you have to deliver bad news?
What was some good advice that you did not follow? What small town would you like to live in? When was the first time someone close to you died? What was some good advice that your father gave you? Which one of your character flaws would you like to improve? What would you sacrifice to be able to go into space? What was the scarriest moment of your life? If you where an alien and you could abduct anyone on earth, who would you abduct and why? What was one thing that do not (did not) like about being single? If you where crowned king of the whole world, what would your first royal decree be? If you had a time machine and you could go back and change anything, what would it be? Does your heart rule your mind or your mind rule your heart? What do you like (did you like) best about being single? Who is the black sheep of your family? Who is your favorite male movie star? What political 3rd party do you sympathise with ? where were you durring a life changing moment? What is your favorite way to spend a night alone? What is something unusual you like to put on a sandwich? What toppings do you like to put on your pizza? Would you ever sell you blood to the blood bank? Are you more comfortable in someone else home if it is messy of very tidy? Where did you find money when you were flat broke?
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It is human nature there is one universal in conversation; everyone likes to talk about themselves. The secret to eliciting good conversation is to know when to talk and more importantly when to listen. It is impossible to listen during an awkward silence. Asking the right questions is the shortest path toward engaging conversation. As you ask the right question you illicit a response that strikes at an emotional core for you conversation partner. Additionally by selecting the question you have the ability to steer the conversation in a direction you will find engaging.
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The greatest danger occurs at the moment of victory - Napolean Bonaparte