Gidday PolyVacuum and welcome to the forum!
Wow you sound just like me when I got divorced and started to date again. It can be terrifying!
But you know what? There is every chance the person you are dating will also feel the same way. Doubts like 'Will he like me, is my make up OK, is my dress too short, what will I say?' and on it goes.
The turning point for me was when I saw a very ordinary looking guy being interviewed on TV about how he managed to go out with such stunning girls.
He had three secrets:
1. Be yourself in every way. Chatting is NOT a competition or chance to score points. Inside you is a person that some girl will think is wonderful so don't hide it and pretend to be someone else!
2. If you are nervous, or excited, say so and why! The girl will think thats cute as it shows you are vulnerable, and it opens the door for her to say how she is really feeling as well. Again, its not a competition!
3. Ask questions about herself. I think this is hugely important. Ask about family, friends, work, hobbies, interests and so on. The key is to LISTEN intently, respond often, show interest, and don't butt in - wait for her to finish. Don't make my mistake of waiting for an opportunity to talk about yourself, or what you did that is better than what she did.
That's it - pretty simple really! But it did take me a couple of goes to get it right, by that time is was fantastic and girls were telling me I was the only guy for ages to take an interest in them.
The other positive outcome of this 'method' is that the positive feedback you will receive will help greatly with your other fear about feeling bad. Here is this nice girl giving you compliments - how can you feel bad about that?
So I hope this has helped a little PolyVacuum, think about it, try it and see what happens!
I am very happy to discuss further if you feel that might help.
Good luck! The Bro