First thing, set the correct goals. You’re touching on it in your last sentence. You’re looking at too big of a picture. Have something easy to find out. For instance, just find out what the best meal she’s ever had was. You’ll spend more time concentrating on asking that and it will make you less nervous. Also, it is an easy goal to achieve. When you achieve it, it makes you happy and you’ll want to do more. Then, as you get better/less anxious, up the difficulty level. “I’m going to talk to 5 women tonight. I’m going to spend at least 5 minutes talking to each person. I’m going to find out where their dream vacation is.” Consider it like weightlifting. It will be uncomfortable, but every time, you’re building yourself up. As you incrementally increase what you demand of yourself, it will become easier and easier.