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Ask His Friends
Let's say you're just getting to know your man. You ask him a couple of descent small-talk questions, but you really want to get to know that other side of him that he doesn't just come out and say. Get to know his friends a little, but don't get into their lives too much or he'll think you're just using him to get to his friends. Never EVER start off a question with 'Don't tell ______ I said this okay?' because he'll be sure to tell him RIGHT AWAY. Try to find out something a little embarassing, and then when you're with him, try a little teasing. 'I know a little something about you.' And smile, eagerly awaiting the, 'What?' that follows. And start to tell him, but don't tell him EXACTLY what you know. Try this and see where it goes from there.