I would recommend meeting up with some like minded guys and go and approach women, it would be even better if you could find some more experienced men or pick up artists to show you how its done and give you advice.

If this is a step to far then just start up conversations with people (men or women) to build up your confidence.

Remember even if things don't go as well as you had hoped it's ok, use it as a learning experience, you haven't failed you just haven't got to where you want yet.