1. Don't take too long before you act. If you are going to think about it for 6 months before you eventually ask a woman out on a date, chances are that she will already have found a partner.
2. Only two things can happen. She can say "yes" or "no". Most of us tend to totally ignore the possibility of it being a "yes". Instead we focus on a negative result and by doing this we are setting ourselves up for failure. Be positive and let it show. Your prospective date will easily pick up on your lack of confidence and it can only negatively affect the outcome.
3. Don't ask others. Do not discuss it with all your family and friends and the postman. If you want to ask someone out on a date, just do it. It will not help to consult others in the matter as this is a personal matter that you need...