Reminds me of The Screwtape Letters, which seems to come down hard on guess culture (not so much rejecting it as not considering it in those terms to begin with, which seems to be common on both sides):

Later on you can venture on what may be called the Generous Conflict Illusion. This game is best played with more than two players, in a family with grown-up children for example. Something quite trivial, like having tea in the garden, is proposed. One member takes care to make it quite clear (though not in so many words) that he would rather not but is, of course, prepared to do so out of "Unselfishness". The others instantly withdraw their proposal, ostensibly through their "Unselfishness", but really because they don't want to be used as a sort of lay figure on which the first speaker practices petty altruisms. But he is not going to be done out of his debauch of Unselfishness either. He insists on doing "what the others want". They insist on doing what he wants. Passions are roused. Soon someone is saying "Very well then, I won't have any tea at all!", and a real quarrel ensues with bitter resentment on both sides. You see how it is done? If each side had been frankly contending for its own real wish, they would all have kept within the bounds of reason and courtesy; but just because the contention is reversed and each side is fighting the other side's battle, all the bitterness which really flows from thwarted self-righteousness and obstinacy and the accumulated grudges of the last ten years is concealed from them by the nominal or official "Unselfishness" of what they are doing or, at least, held to be excused by it.

I've tried to keep that generally in mind as a reason to be as direct as possible; it's only recently that I've been aware enough of the dichotomy in popular advice to start collecting quotes about it.

Also possibly related:

If you have two choices, choose the harder. If you're trying to decide whether to go out running or sit home and watch TV, go running. Probably the reason this trick works so well is that when you have two choices and one is harder, the only reason you're even considering the other is laziness.

...from Paul Graham via EY. I usually think of asking for something as being harder than trying to find it myself or doing without; for one thing, it's an action now versus a possible action later.