When I meet somebody who interests me I go through the traditional social practice of asking them simple questions to break the ice. however I have never been either simple nor traditional I like to dig right into who they are to see how we might connect with questions that others might not ask them and they even be personal as we go along. I am always open to doing the same I don't hold back and I don't hide anything. I try to be creative and sometimes a little deep. but after those initial questions here are just two I might choose to ask especially if the person says "Ask me anything?"if we ever talk or meet by the way that is something you absolutely do not want to give me the ability to ask they'll probably end the conversation. I like to play nice though but again ask something to get to know them. Feel free to answer if so inclined: 1. What is one thing your life has taught you good or bad that you never expected? 2. With your permission where I to ask two of the people closest to you right now to privately tell me what they think your greatest strength is and maybe your biggest weakness how would they respond and would they be correct? * A clarification saying that they would respond "Who the hell are you? Leave me alone and mind your f#cking business!", does not count as a response to my questions. Only my parents could get away with that when I was a child asking them what are we doing this weekend. 😆