According to Osho, the real question can’t be asked because it lives at your innermost center; when you reach it, the answer appears simultaneously. What we ask are peripheral, unreal questions—hence the sense of stupidity. Still, ask and exhaust them, then drop them; recognizing the false as false ripens you for the truth. The criterion: if an answer won’t change your life, the question is useless.
Real questions are so deep that when you find them you instantly know the answer, so the askable ones feel fake—and that’s why you feel silly.