I like to have a good idea what the situation is. The problem is [...] apparently I'm supposed to figure out what she wants on my own without asking.
No, you're supposed to pursue what you
want in a gentlemanly and respectful (yet fun and easygoing) manner. If she wants the same, you'll be able to tell, and things will progress.
I'm sorry that you've had negative experiences in the past (that anecdote about being summoned to a meeting with counselors is indeed pretty terrifying), but there's no simply substitute for confidence (a subject discussed in the Guide