It's nice to hear your update. The actions you describe are those of a man who is clearly interested in you. I think Jim is on the money when he encouraged you to reciprocate by flirting back if you like him. It might be that he has heard about your sitch and might be wary of being too forward. Give him signs that you are interested.
Regardless of what happens with him, it is great to hear that you are putting yourself out there and getting on with your life and enjoying yourself. Take that happy moment and build off it.
W 34 Me 42 Married 7 years together 8 0 kids 1 beloved dog BD 4/6/2018 I moved out 4/7/2018 I moved back in alone 8/05/2018 I file 3/06/2019 D official 5/7/2019