Hi WHG, thanks for the feedback, I do know what you mean and I agree.
In regards to this situation, I actually was trying to be specific, in the context of the conversation. We were talking about what we were going to do instead given the bad weather. I was talking about doing 'X', and he was telling me he had no plans if we canceled the original plan. So I was paraphrasing when I said 'can we hang out', we just hadn't figured out what the new plan was.
I dunno, maybe that is the problem and I don't realize it. It doesn't seem like that was the problem after the fact. Lately he makes me feel like he wants/needs me to chase him, and then the next minute he doesn't. It is literally like dealing with a yo-yo. How do I know when the right time is to do those things without rushing it?