Sorry I’m late to the party. Sounds like you have covered a lot of ground. I just want to vote that he sounds attracted to you, but not necessarily intent on pushing it very hard, but then also perhaps secretly hoping for encouragement. Also, I work with many women 15 or 20 or so years younger than I, and it’s hard not to notice how pretty many of them are – still, I think I’d be pretty worried to be acting as flirtatiously as I think he is, especially if I were in a position of authority.