Start off by thinking about your strengths and weaknesses on dates. Only once you understand what you can improve (and what you should just leave alone) can you begin to make advances in your dating skills.
Date as often as you feel comfortable.
Like anything else, people improve their dating skills with practice. This doesn't mean you should schedule 8 dates a week but, if you want to improve dating skills, take up opportunities to go on dates as they arise.
Watch an expert at work.
If you know someone who is renowned for their dating skills, try to set up a double date to watch someone apply a personal style to dating. Don't try to emulate the person. Just observe to gain some tips and pointers to improve your own dating skills.
Be honest with your date.
While asking directly about your dating skills is not the best way to get a fruitful answer, raising a conversation about the date itself is. Try to talk with your date about how things went and what he or she liked and disliked in order to get an idea of your success. Remember, though, this is a conversation packed with potential awkwardness, so keep it light and casual.