1. What are your personal goals?
You SHOULD know what it is that he wants to do outside of a relationship, because he is going to want to do them. Most women get in the way of a man's personal goals, because they want all of his goals to involve her. Accept that not all of his goals involve you, as they were formed before you...and some simply will not involve you regardless.
2. What was your childhood like?
Knowing a man's childhood is like being given a key to understanding everything he is about, because it will explain why he is the way he is. This is something every woman should know from top to bottom.
3. What are your insecurities?
These little devils will pop up out of nowhere if you don't ask and don't get clarification. When they do surface, they usually ruin and destroy everything good, so it's something you MUST discuss and find out early on, so that you know how to handle it or you are aware that it's just insecurity when it surfaces.
4. What career path are you interested in?
This is a direction every woman should be aware of, because it could involve him moving away, or having to spend a lot of time at work etc.
5. What do you expect from a relationship?
Not everyone's idea of a relationship is the same. It's good to clarify this early on and figure out what a relationship really is to him.
6. What do you want out of life?
This encompasses everything he expects to accomplish out of life, if that includes his career, a family, financial success etc. in essence, it's all of the major goals he has for himself until he dies.
7. What can't you stand?
Imagine if you spent your entire time doing everything he hates, because he never tells you? This is how 99.9% of relationships are, and it's why they fail, because women never actually know that it is that they are doing wrong, and they never find out what it is that their man actually can't stand. It's good to know his boundaries here.
8. Do you want children?
Some couples never discuss this, so when one of the partners declares they'd like kids, they are shocked and torn apart when they realize their partner never did. If you want children, and even if you don't you need to ask him if that's something he is looking forward to or not.
9. What were your past relationships like?
A person's relationship past can show you patterns in their personality. It is also good to know, to find out if a man still hasn't moved on, if they have baggage, if they are the cheating type etc... which is not something you want to find out later.
10. What attracts you to women?
A general question that goes beyond the superficial. Everyone has their unique idea of an ideal partner; it is good to know what is actually ideal and attractive to a man in the first place.
11. What expectations do you have on yourself?
A man's expectations on himself will rub off onto everyone else that he encounters, if they don't fall into those expectations; but more importantly, a man's expectations of himself can determine his reactions and actions toward many things.
12. What are your views on spirituality?
Religion matters to some, to others it does not. However, it is important to find out if it does matter to your partner, and where they stand on it, and if they can accept you into their life with the beliefs they have.
13. What do you expect from a partner?
What does he want from you? What does he need? What things are the most important to him, from a woman? What kinds of things is he looking for from his partner?
14. Describe your family and friends?
Who are they, what are they about, how does the family function, what kinds of relationships are there etc? All of this shaped who he is today, and may shape his ideas on the kind of relationship he wants. Get to know his family and friends.