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ikrase comments on LW Women Entries- Creepiness - Less Wrong
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I tend to get bogged down in infinite regress of 'Should I ask if it's okay to guess? Should I guess if it's okay to ask if its okay to guess?'.
My usual way out of this is to introduce other levels of indirection. E.g., "I often wonder whether it's OK to ask people X in situations like these. It's tricky, because sometimes not having asked is taken as demonstrating a lack of interest in X, which is of course a problem when I genuinely am interested, but on the other hand sometimes asking is taken as expressing too much interest in X, which is of course a problem when it makes people uncomfortable. Oh, look, pie... would you like some?"
Of course, this is within the context of my goal being to communicate my state meaningfully enough that other people can make meaningful decisions, which I understand is only one of many possible goals.
I... uhh... don't really understand what you mean. Except that I wish I had some pie right now.
Of course it's often moot since I operate similar to Yvain does (i.e. though opera-worth crushes that have to be toned down to a ludicrous degree to avoid scaring off even totally interested people).
To be fair, I often get that reaction.