One mistake I have seen many men make as they start learning to become more confident with women is that they make some progress with a woman and then stop. Perhaps the conversation stalls momentarily after they have some strong initial interest. Or maybe you start trying some methods of communication that are new to you, i.e. humorous banter, being more teasing and challenging to the woman and they are working but then you slow down or stop doing what was working. The advice I have is if things are going, then KEEP GOING until you get to a point where you can’t go any further and then wait until that point and then stop.
This is where playing it “safe” can really be a problem in part because you have lost sight of your goal. Assuming your goal is to have a sexual relationship with a woman that you are attracted to and have started talking to it might be tempting to stop at some point and ask for a phone number. Depending on the logistics of the situation this might not be a bad thing. For example you meet at a coffee shop or some other time where one of you has to go for some reason that can’t be changed, i.e. getting back to work etc. However if you could have continued the interaction you are better off doing it right then while you are in a good state and she is also in a good state.
One concept that I think is very important in any area of life, but especially in your communication with women is momentum. If things are going well, let the good times roll. However if things are interrupted you do have rebuild some of the emotional states that you have established before. This advice is not meant to be universal, sometimes you do need to stop because of logistics or circumstances, however being resourceful and focused on your end goal will keep you on track if you want to keep it going.
Another important concept is to be determined to do what works. I don't mean this in a way in which you are compromising your values or doing anything deceitful. Rather I mean do things that are getting results rather than doing what you are familiar with if it was not working in the past. Changing the way in which you communicate with women won't always be easy or feel comfortable, but if you are committed to pushing the envelop then you have a chance of getting results that might go beyond what you ever could have imagined was possible.