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best way to do this is to find out that guys field of expertise and then ask him a question on that. You will definitely get a conversation started and would last long if you'd keep comin up with interesting questions about his expertise. Men like to be in-charge, and by doing this you'll make him feel incharge and that will make him feel very comfortable arround you, which will lead to further conversations.

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Q: How do you start a conversation with a guy if you are friends but not good ones?
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