casebash comments on Subjective vs. normative offensiveness - Less Wrong Discussion
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Maybe there were signals, but they were just friendly signals. Regardless, this isn't relevant to the question. You're ignoring the hypothetical.
I'm not really. Being creepy isn't about violating a straightforward rule such as that 40 year olds shouldn't ask out 20 year olds. It's about not reading the signals in an interaction and as a result having a bad model of the other person and engaging in actions that make them uncomfortable as a result.
A person purposefully sending friendly signals might still say no when asked out, but they generally don't get creeped out.