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He's practiy told you he won't make the first move and obviously likes you. I'm guessing he is afraid of looking like a fool for going after a much younger woman. So stick your neck out already. Seeking Married or single. It doesn't need to be as majorly awkward as you're dreading in advance, and if the answer is no for some reason, it clear the air to have discussed it. I find most crushes dissipate in a hurry once I figure out that the guy really isn't into me that way. It's the state of uncertainty that fuels it. I would wait till we are alone and ask the following question: "Would you kiss me if I asked you to?" Any who is sentient and interested should go for that. If he ignores the question (when he clearly heard you) he need a few days to process and act on the offer, but you'll know within a week, I think. If he tries to laugh it off, or gives a firm No, you have your answer and can go about your business, knowing that you tried.
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