Man, I don't know what to do other than go to toastmasters and work on my confidence and social skills. I have deep inner game problems and, I even notice, I tend to obsess over negative thoughts and worry too much. For example, before she got to work (because I was there first), I was obsessing for an hour about what to say to her, and I could come up with nothing. It's like I don't trust my social skills enough to just think of nothing to say to her and hope it comes off naturally right when I approach her, which I also hesitated to do for a good 15-20 minutes. I also was comparing myself to other people at work talking to her and having fun and it caused me to feel worse about myself.
Now, we were supposed to be going out Tuesday to the zoo, but I'm pretty sure after this she doesn't want to go out with me anymore at all. She sees me as needy, socially awkward, insecure, and boring. I'm pretty much positive there isn't any attraction there. There's actually a feeling of awkwardness when we're around each other, but much more at work then outside of work. So, I don't know if I should tell her I'm on for Tuesday or not when I know she probably isn't looking forward to it.