POLL: A man should be self-assured, even if the woman he's trying to interest seems disinterested or is not being very proactive (like suggesting future meetings or taking a hint he makes about a future meeting)? (but not obnoxious about it, of course) That, or he should "try not to bother her" as much as possible, and never assume that she's interested in him unless she makes obvious overtures towards him? Or something else?

Don't bother, unless this is a game of Conquest