Good question. I'm very shy in the "real world." I had a short thing when I was about 15/16, then nothing for another 10 coming up 11. Now hear I am, 26, and unable to chat up any females. A female friend has said I'm not that bad looking, so that's not the problem. Now that I have decided to work past it, I just don't know how.
I have some personal space boundaries too, so it's difficult. a little OCD, made worse by stress. And now that I have been actually trying with women, and my lack of ability is making it near impossible, I'm getting more stressed, making the obsessive behaviour worse. All a downward spiral for me.
So, I knew I needed to break the cycle, which is why I made an effort with women again in the first place, but my lack of ability was still holding me back. I therefore needed to break the other cycle then. As soon as I mess up, i destroy my chances as a way of self sabotage. To break this I concluded I had to just practise with women, and break the sexual tension.
So, I can see somebody and get it out of the way. As a result I'm far more relaxed than I have been in years. I'm able to focus on my coursework again (I'm a student, just went late back to a degree, as my odd behaviour made it difficult for me when I was 18), I can chat to women without that massive testosterone rush, and makes me feel a little less undesirable, which had become a massive problem to me.
I am now happy and satisfied, and a girlfriend is less of an issue. I'd prefer that by far, but this makes it easier for me to overcome my women issues.
There is a girl I have been trying to chat up for ages, with minimal success. She has a great body, not the prettiest girl, but with the amazing body, she is not far off what I like. She really really likes sex, so i figured not that hard to chat up... I still screwed it up repeatedly, and went into self destruct mode each time. managing to turn it around, to do it again. Well now I am suddenly less desperate, and have managed to turn it around again, with all my women issues slightly resolved, I can talk to her without freaking out. I'd feel bad about trying to pull her while also paying some other women, but I know for certain she has paid a guy on more than one occasion, and as we aren't a couple at present, it's ethically ok in my books.
So rather a long explanation I guess, but all boils down to confidence I guess. It has helped massively. I feel more like me, and can do my normal things again, without all my own personal brand of crazy stopping me. I haven't felt this great in years.
And of course it helps that I get to do things with girls who are waaaayyy out of my league. I can only realistically get average girls. I passed up some opportunities when I was younger, and still in my unable to touch people phase. Some really hot girls too. I'll never get those opportunities back, so feel I have to make it up to myself.
Only tried two girls, one of which twice. I'd like to try a few more, get some more experience in, but am not in any rush (and finances agree!).