Comment by Galacta7

Hmm, I see a problem with this analogy in that the person selling the stamp is at an unfair disadvantage due to that information asymmetry. It's actually unethical and sometimes even illegal to do this in the stock market, especially if the knowledge wasn't publicly available.

I think askers sometimes feel put off by guessers, because you can't inherently know what the other person thinks is a fair request -- unless you're in a high context environment (which most askers won't be as familiar with). So from their perspective, guessers are doing a bit of insider trading ... only they know what's of value to them. It's frustrating from the askers POV because the counterparty seems less than transparent about their true intentions.

Of course, from the other side of the coin, the asker is ignoring a million cues that are obvious to the guesser but meaningless to the asker who doesn't even know to notice them.