Okay, I just read my own long ass post, and I feel I have to say to you, Mr. Sangheili, that this it is based on a number of assumptions I have made about you solely based on your posts on this forum, and further that it's put into a frame that fits my own experiences. This may not apply to you at all. If you're willing to read it, take from it what you can, and if there's nothing for you to take from it, just ignore the lot.
Many great things said in this thread. I will echo some of what Swoon has said. You seem to suffer from social anxiety, and I would guess that this doesn't only show in your interactions with women? Anxiety is worst when you're at your most vulnerable, when you have to face the thing that scares you the most. Learning to live with anxiety is about relishing the small victories and slowly building on them, one baby step at a time. At some point, what once felt like a small victory will seem like an insignificant occurrence. My advice to you is to accept in a very literal way that you have trouble communicating with women because you suffer from social anxiety and not the other way around, meaning that what you need to work on is dealing with the anxiety, not on communicating with women in a flirtatious manner. Meaning, and this is the last meaning for now, that you should accept that dating or picking up women probably just isn't in the cards for you just yet. Start at the bottom and work yourself up the ladder.
Some seven years ago, I was paid a visit by a massive panic attack. In one instant, I was completely incapacitated for a long time. It's a completely different thing. I was sure I was dying, but the exaggerated response to something that really holds no danger is kind of the same as what happens with people who suffer from social anxiety. After the panic attack, I became a complete shell of who I used to be and who I still considered myself to be. When I was home alone, I suffered from panic attacks all the fucking time. I couldn't be without my girlfriend, which obviously I had to do, as she couldn't babysit my all the time. This was my first step out of the slum, and it took time. The next step was to gradually learn that I wouldn't die from moving when I was alone. Then that I could eat without dying even when I was alone. And so on and so on. I was terrified of eating when no one was there to supervise how my system would react to the food, but I was no longer afraid of simply getting out of bed and walking to the kitchen. And things moved on like that, slowly but surely. Suddenly I would eat, but still the thought of leaving the apartment terrified me. Then I started to leave the apartment, but never for too long. At that point, I had no issue actually getting out of bed. And so things moved on. Gradually the things that once scared me would take a backseat to new things, until they didn't scare me anymore. By now I practically function like I used to do (though the anxiety isn't something you will ever completely get rid of). But though I wouldn't refrain from taking catching a completely empty airplane to NYC today, forcing myself to do so back then would have been catastrophic for my condition. You have to take the small victories, one tiny victory at a time, and make sure to give yourself a huge fucking high five when you come home with one of those small victories. You will get knocked back again and again, but if you refrain from taking on challenges that are too big at that specific point in time, things will gradually improve in general. Ever so often, I would take on a challenge that was much bigger than I could chew, which would knock me way back. Most people with anxiety do not learn from those massive defeats, they are only work to reaffirm their fears and worsen the anxiety. When people say "just approach her and ask her out, what's the worst thing that can happen?", they have, in most cases when it comes to people with anxiety, missed the point.
Okay, this is getting pretty long. My point is, of course, that just like catching an airplane to NYC all by myself wouldn't have been any kind of efficient way to deal with my anxiety back then (quite the contrary), you probably shouldn't be going for the big prize from the get go. Accept that it takes time, and start with interactions where rejection of some kind won't feel like a major defeat. Strike up random or meaningless conversations with guys you don't know and aren't going to become acquainted with anyway. Say something meaningless to the guy behind the cash register. Things like that. Whatever makes sense with regards to your specific anxiety. If you have no problems interacting socially with men, then have small conversations with women in settings where meaningless small talk is common and the potential for rejection is exceedingly small.
Also, the thing that helped me the most was telling my friends and family, literally everyone, about my condition. I have always been a very outgoing and social creature, and I was transformed from a loudmouthed idiot to a complete wreck from one day to another, so for me it was easy and only made sense to tell people about it. I know this is very different for you. My girlfriend suffers from social anxiety, and it took me years to convince her to tell her two best friends about it. I know this has helped her significantly. If you have a friend or family member close enough to you, I would really consider opening up about it if I were you. At least at some point.
And finally, consider seeing a psychologist to help you make a plan of how you can gradually overcome your anxiety.