This realization is honestly progress. The other thing to keep in mind is that most other people are just as neurotic and you are (don't take that the wrong way.) What I mean in saying this is that everyone is caught up worried about their own stuff and thinking everyone else is judging them and etc. It's a form of arrogance and self absorption many/most people indulge in.
Once you understand that everybody else is just as neurotic as the next guy, then you realize everyone else is too worried about their "stuff" to be critical of you. And then you can just relax and learn to chill out.
Dave, I have a question for you. Do you think that coming from a sales background that you are selling yourself too much? If you are do you think dialing that back and picking out interesting things the chick says and asking more about that might help keep conversation going?
Believe it or not years ago I was painfully shy. And as I emerged from painfully shy I went through a painfully self-conscious (see self absorbed, above) stage. So I've been through this evolution myself. Now I am truly confident and I have been for years. I don't care what people think about me, I'm not afraid to say what I think, I'm not afraid to open up emotionally, I'm good with who I am and that energy radiates from me and is extremely attractive.
I remember a big epiphany in my journey was realizing everybody else is just as worried about what everyone thinks as I was...so much so that they probably don't even notice whatever thing I was doing that I was hyper self criticizing myself about. Here on the board you are revealing your internal dialogue so it's here for the observing...so we can see it and speak to it. In real life nobody cares nearly as much as you think they do. That was a great relief once I digested it.