Ok, what I understand from your posts is that he might not get the hints (the insurance thing, me looking at him or being intimated..)
Or maybe he got them but is trying to keep the distance because of age gap or his daughter…
I think I will ask him if he is seeing someone next time. But me asking this would not be clear enough as he also asks about my life, how its going etc… I he says he doesn’t see anyone, maybe I could tell him joking, maybe you should try to find yourself a freshly divorced 40 years old blonde woman and ask her out… So if he gets offended, I can says, relax, it was just a joke.
On the other hand, if he laughs and doesn’t respond immediately, at least I will have planted a seed in his mind… And from there he will have to decide whether or not he wants to make a move.
What do you think?