This is what I suspect is happening, since I don't have the nerve anymore for the suggestion of action.Its a pretty fine line between playfulness and flirting. If there is a woman who I am interested in romantically, i am going to try and talk to her in a playful way to build some rapport before asking her out. But then there are women who I might find fun to talk with but I am not attracted to them romantically. I may be playful around them because I find them witty and fun to talk with.
I'm not the kind to flirt for a long time before asking someone out. But some guys wait a lot longer before advancing.
So, I guess I didn't really answer the question because the question is pretty tough. You just have to go with your instincts when trying to read the guy.
I remember my sister telling me the story about a guy who flirted with her forever at work (she is a nurse and he was in hospital administration). And she finally asked the guy one day "so when are you going to finally ask me out." they went out after that and she ended up marrying the guy. So, if you really want an answer you need to be direct.
Nice to have a guy's input, though. And please don't forget I bid on you as a cougar last week.