You are afraid of women. You feel scared when you are out on a date. Well, I got good news for you. THEY are even more afraid. Women are extremely insecure creatures. And you thought you were insecure.
Well, get a load of this: at least you don't spend your waking hours putting stuff on your face and you don't spend all your money to buy clothes to appeal to the opposite sex!
Women are always forever asking themselves the same question: How do I look to this guy? Does this guy really like me?
Where does that leave you? You can start out by liking her. If you are scared, and she is scared, that's no good. That's not a good place to start a relationship. Don't worry about what you say or do. Concentrate on liking her. Just sit there, find something that you particularly like about her (after all, if there is nothing about her that you like, what are you doing there in the first place?) It could be her smile, her "boobs", or whatever, just stay with the thought, think about the things you like about her, until you feel a real good warm feeling glowing inside of you.
Again, don't worry about what you say or do. Women have their antennas out, probing for psychic current of like/dislike floating towards them. It's really hard to fool their radar, so don't even try any Oscar-winning performances, please. Just assume for the time being that she can read your mind, OK? If you really like her (inside of you), she'll know it.
No need to try to impress her with your accomplishments, your effervescent personality, your sense of humor, or tell her your problems. She wants to talk about the most important person in her life -- herself. Let her. Your goal is to make her talk, and listen. Surprisingly few guys listen to women, or maybe they listen but they don't pay attention.
Again, don't worry about how you look to her or what you are saying. Focus on her and your good feelings towards her 100 percent. And CARE about her story. If you can't do "care", at least you can do "kinda curious", can't you?
Look her in the eyes. That establishes an unspoken communication channel that conveys your feelings (and turns her on, as an added bonus). And once that invisible "flow" between you and her begins (don't worry, you'll know it when it starts) the right words will come to you.
WARNING: You wouldn't think of going out on a date wearing dirty smelly underwear, would you? And you probably won't be wearing your work clothes that you work on you car in, either? Well, get a load of this: showing up on a date when you are seriously upset about something, or worried, is as bad or maybe worse than showing up smelling like an elephant's butt. Because she will sense your bad feelings and take them personally, she will think it's about her, your upset will pollute the whole atmosphere.
So she is sitting there, basking in the warm appreciative glow coming from your direction, and she is beginning to think "Hey, this guy really likes me". And since you like her, she'll like you back! We all like people who like us, it's only human...
She'll probably do most of the talking anyway, so your job is mostly to just sit there, completely relaxed, and like her. Once your feelings are firmly established in her mind, man, you've got credibility. How about some compliments! Don't overdo it though. And above all, don't be crude. Limit your comments to the VISIBLE parts of her body, like hair, smile, eyes, hands. Leave the boobs and butts alone for the time being. And above all, don't be phony. If you think her hair sucks, don't say it's beautiful. Just shut up, will you. But if you kinda like her hair, why don't you just say she has beautiful hair? It won't kill you, you know.
IMPORTANT DISCLAIMER Unless you get to like her inside of you, NONE OF TIPS ARE LIKELY TO WORK. Once she feels you like her, you can exaggerate your feelings and generally bullshit and get away with it. If you feel nothing, then she feels nothing. Just leave her alone, find somebody else. There are billions of other women out there. If you try to b.s. your way through, you will be exposed for the fraud and creep you really are. Don't be completely phony!