ChristianKl comments on Subjective vs. normative offensiveness - Less Wrong Discussion
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So your actual rule is, "people who are bad at reading subtle signals should never ask women out"?
If there existed signals that were reliable indicators, you'd expect numerous people to have posted them online. The fact that you have to explicitly disclaim them is evidence that such signals don't really exist, or are unreliable. Here's another theory, a woman freaking out has more to do with how you ask and who's doing the asking, specifically whether you are perceived as a high status "alpha", a low status "gamma", or somewhere in between. In particular "If you frequently freak out woman with asking them out then you reduce the intensity of what you ask women" is horrible advise since it will make you be perceived as lower status.
If you frequently get turned down in a way that freaks out the woman, that means that you have a lower status. If the woman then tells other people about how you are creepy you will lose a lot more status.
On the other hand asking a woman whether she has is single is in many cases not inherently a low status move. Various forms of flirting are no low status moves.
Even if don't really care about the woman, when a male friends acts in a very uncalibrated way and asks a woman out in a way that freaks her out, he loses status in my eyes. The same is not true with male friends who are calibrated and flirt in a way that the woman could turn down.