This is really more for new guys than anyone else.
Though I have still sometimes seen intermediate guys making these mistakes too.
In school, you probably learned "There are no stupid questions."
Well, that might be true in school. However, in dating, it is not. Because when it comes to women, there are absolutely a lot of very stupid questions that you should not ask.
We're not talking about questions like "How old are you?" or "How many guys have you been with?" that various stern women claim men should "never ask a lady!" or that "don't matter!" on various feminist-leaning blogs or news sites around the web. Those questions are actually perfectly fine; I suggest you ask both regularly (the second works better after sex, though).
However, there exists a certain class of question that, when you ask from it, conveys a degree of neediness, uncertainty, and lack of leadership that repels women like oil does water.
These questions are the ones we can, for our purposes, safely dub stupid questions.