I think that in practice, you don't need to be psychic. I think the judge will ask "would a reasonable person know this behavior, in this context, would be like

I think that in practice, you don't need to be psychic. I think the judge will ask "would a reasonable person know this behavior, in this context, would be likely to cause offense?". The reason for it being dependent on the other persons feelings is that you can't just say "sure, I know she's a prude, but most women wouldn't take offense to that". Like I said, the law tries to be reasonable. Will a judge or jury say "Your behavior was that of a reasonable person, and there's no way you could have known that asking her out would cause a flashback to (whatever), but it's her feelings that matter, not yours"?