“How old do you think I am?”
Did you ever find yourself in a situation where somebody (usually a woman) asks you to guess their age? You don’t have to be a guy for this to happen to you; a lot of women are equally happy to ask this of a man or another woman. And a woman would be faced with the same problems when answering. It’s a good candidate to be the most dangerous question in the world of social interaction. There is no safe way to answer it.
You might answer truthfully, without thinking or wanting to insult the asker. You think it’s a simple answer to a simple question.
Except, it’s not. You might get lucky, and your estimate might be lower than her actual age. Then again, she might look a hell of a lot older than she actually is, and there you go, open mouth, insert foot.
You might be tempted to subtract a few years from your actual guess, which is also not without risk. Most women who look their age or older know that, too, and if you say something to low, they will see through that and will still feel insulted.
So, I usually plain out refuse to answer. I tell them I’m bad at guessing, and if they insist, I tell them I never answer this question because it usually causes problems, even if you try not to make a big deal out of it. It’s a tricky question that’s usually asked out of vanity, although I’d be very careful to suggest that to the asker ;-). If I’d know her well enough I might, but if you want to do that you’d better be damn sure she can handle it.
Unfortunately, my method only works for women. If you are a guy, possibly in early dating stage, I’m afraid I don’t really have any good advice for you… except maybe, turn tail and run? 😉