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once you start talking about hobbies and activities outside of work you can work in a few phrases that let him know your interested. If he's interested, he'll take the bait. Phrases like: "You are triple threat kind of guy; hard working, good looking and talented/interesting/whatever." Or "I wonder if you ever get lonely doing X all by yourself?" It also be that he's not ready to date. His divorce wasn't that ago. relationship type or good friends type
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