r/Fitness does a weekly "Moronic Monday", a judgment-free thread where people can ask questions that they would ordinarily feel embarrassed for not knowing the answer to. I thought this seemed like a useful thing to have here - after all, the concepts discussed on LessWrong are probably at least a little harder to grasp than those of weightlifting. Plus, I have a few stupid questions of my own, so it doesn't seem unreasonable that other people might as well.
Boy did that set off my creep detector.
Of course it always depends on your preexisting relationship and other factors. You always have to calibrate to the situation at hand.
A lot of people automatically form images in their mind if you tell them something to process the thought. I know the girl in question from an NLP/hypnosis context, so she should be aware on some level that language works that way.
In general girls are also more likely to be aware that language has many lavers of meaning besides communicating facts.