Pugly wrote:
It's very very easy for my brain to hear these words and have it run off in countless possible permutations.
That's fine because there truly are a ridiculous number of possible meanings of this phrase. The specifics of a particular use of it are more or less impossible to guess.
Pretty much, hearing that statement (at least to me) makes me feel "comfortable" making similar statements to whoever it is, but I'd tread lightly with it, because if YOU are overanalyzing it, there's a good chance that SHE will too if she hears that kind of thing.
I actually will use that exact statement for the simple purpose of getting a response from the other person, and then attempting to gather information from the response that I don't want to directly ask about

The phrase can be incredibly loaded at times so you have to look out.