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Better a late response than never. I would ask him: 1) if he is dating anyone; 2) where he goes out at night, bars, eating, etc.; 3) what he does in his free time; and 4) a question everyone is asking each other this week-straight and are you in favor of marriage and why or why not? Also, your post does not say whether you are out or not. If you are out, you can just tell him and what happens. I assume that you are not out-at least to people in your industry. Also, get him drunk on some good wine-alcohol causes interesting things to happen Chicago women wanting sex
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