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How long should you wait?

How long after a date should you let a guy know what your are looing for without sounding to upfront?
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Making the assumption that he also appears to be looking for more than a first date...what’s wrong with sounding up front?

Confidence is attractive (but conceit isn’t) and I would think a woman who knows what she wants and says it, would be attractive too. Unless it’s not what he wants, but if that's the case, why waste his time or yours?