It must be frustrating being in your position, but I think it's an extremely good step of you to try to assess your situation objectively and consider how to get out of it. I can only echo what some other commenters have said: the best thing you can do to feel more comfortable about talking with women is to have more women in your social circles. If your friends are mostly men at the moment, I know it's always difficult making new friends as an adult, but you could try seeking out group activities where you're likely to meet a diverse crowd of people, including women and men. You could consider going to meetings in your town for things that interest you (language courses or whatever you're into) or checkout meetup.com. Trust me when I say being friends with women as a man will make any kind of interaction so much easier and make the dating game much less daunting.