In middle school, some of my friends and I discussed systems for transmitting information about crushes. Wouldn't it be nice if some trusted person knew everything, and could tell you whether your crush liked you? But then we faced a certain use case. One of my friends liked a girl; if she liked him back, obviously he would like to know that; but, he said, if she didn't like him back, then he didn't want to know that, and would prefer to keep hope alive.
So, we thought of this: Have some trusted person learn her preferences, and then flip a coin: if heads, then tell him if she likes him (and say nothing otherwise), and if tails, say nothing either way. This seemed to serve pretty well. [This was all hypothetical, of course.]
I think this is a good koan--something to provoke further thought. For example:
1. This is sort of how a scientific investigation may go. Suppose you have some theory, and some test that only yields results sometimes: 50% of the time, the test will yield result A, but 50% of the time, it will work properly, and in that case, if your theory is right, then the test will yield result A, and if your theory is wrong, then the test will yield result B. (Example: "There are no animals in this area", and imagine that they'll try to avoid being caught and that you can conduct an exhaustive search of only half of some area at once. Or: "Bob isn't holding a key in his hands", and he'll only let you look at one hand at a time and can switch from hand to hand between searches.) Repeated testing will let you approach certainty about your theory (but never really reach it).
2. One could talk about Bayesian probability and priors. Especially if one varies the coin's heads/tails probability.
3. I think this sort of thing is an actual trope in human interactions. Some people give "hints" of various sorts; to hint proposition P might be defined as "to decide to do some action X such that, if not-P, then there's a small probability that a generic human in your position would do X, but if P, then there's a high probability that a generic human in your position would do X". Other people (well, probably the same people) may perform tests, to put some other person in a position where he might do X or something else, and if P were true, he would do X with high probability, but if not-P, then he would do X with low probability. And people who resent such "tests" may deliberately randomize (or genericize) their behavior.
Consider this: Imagine that someone has asked me a question to which, if P, then my answer is rather embarrassing, and if not-P, then my answer is not embarrassing; suppose lying is not an option. Suppose I am a naive person. Then, if not-P, I will simply give the non-embarrassing answer, and if P, then I will refuse to answer or something. Now, if everyone knows I am naive, and P is true, then refusing to answer is futile; everyone can see that and deduce P anyway.
Considering the above, I might decide to be a defensive person. I will recognize questions like that, and at least some of the time, I will simply refuse to answer even though the answer is non-embarrassing. It seems people do exactly this: refusing to answer "personal questions", as they are called, seems to be relatively common behavior. Even on the scale of just you and someone else, you can establish yourself as a defensive person by refusing to answer a personal question when the answer is innocuous, and maybe revealing the answer through some other means or at another time (be a bit careful: e.g. if you refuse to answer, he pressures you to answer, and you say the innocuous answer, then it would still seem to make sense next time you are pressured and still refuse to answer to deduce the embarrassing answer); then, the next time you refuse to answer a personal question, you have demonstrated that this doesn't necessarily imply that the answer is embarrassing.
It seems to me polite to act as though someone has won his status as "defensive" without making him work for it, and rude to do the opposite. Or to make it irrelevant. "May I ask <personal question>" makes it easy for the person to say "No" (much more so than just asking the question), which establishes that "no answer" might easily happen even if the answer is innocuous. (I also take the parallel approach that it shouldn't be embarrassing to tell me anything. I think embarrassment is the anticipated feeling that someone might tease you/put you down for something, and so if telling me something won't lead to that happening, then you needn't be embarrassed to tell me. Then my task is merely to make that true.)
Consider also encryption. Suppose people are naive. Then they won't encrypt anything (and do other things to make their information inaccessible to others) unless they have "something to hide". Then goddamn authorities can say "This person is hiding his stuff, so he is probably guilty, and that's all the evidence we need to justify using forceful means to make him reveal his secrets", and there is little defense against this. (In some situations, you may have an obviously "legitimate" reason to hide things, like hiding your company's information from your competitors. But there are other situations, like if the government comes and demands that information (ignore the possibility that they'll leak anything--I imagine the government will claim that's ridiculous, and I imagine most people would buy that), in which those reasons don't apply.)
Meanwhile, if people are defensive about encrypting and hiding their stuff, then statements like "If you had nothing to hide, then you wouldn't be hiding anything" are obviously false. Imagine trying to make that accusation of Bruce Schneier or Colin Percival. Now if only people like that were extremely common, and considered the norm. (Oh, another example is the "Don't talk to the police" crowd.)
If nothing else, I consider it rude to demand potentially embarrassing or incriminating information from someone who isn't willing to give it up, and use their response to get that information anyway; and I'd rather rude people not win out relative to non-rude people.