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 gods had condemned Sisyphus to ceaselessly rolling a rock to the top of a mountain, whence the stone would fall back of its own weight. They had thought with some reason that there is no more dreadful punishment than futile and hopeless labor. - Albert camus