Sometimes my clients ask me if I've ever done time. I don't think they seriously wonder, I think they're really asking whether I can be sympathetic.
It'll happen like this: Client will be contemplating a plea to some jail time. Thinking about it aloud, he'll say something like, "I don't know, its rough, that's a lot of time." I'll say something like, "Well, I just want you to know that it could be worse after trial." Then, he'll say something like, "Miss Justice, you ever done time?"
And, just once, I'd like to say (with a straight face), "2 to 4 in State."
Ha! That'd be funny.