Hey @crhothem, welcome welcome! Glad to have you join us here
First thing I'll say is that @ahmed is right, but it's weird how that manifests itself. In my experience, the ONLY thing that really, truly blew me past my approach anxiety with pretty girls, was having a lot of pretty girls in my life, and just pushing myself. But I've seen guys really short-circuit the process in our live training programs with bombing openers. I know we talk about those on Say Hello in part 3. If you just balls up, and go do some bombing openers on really attractive women, it does wonders for your confidence. They're tough - gaining confidence with bombing openers is like closing a wound by sticking a hot coal to it - but they work fast. By this time next week, I want to hear field reports about 3-5 times you tried them!
As for where to go when you're asking questions, there are a few things you can do... rather than ask a question, you can make a guess. So instead of asking 'where are you from' you can say 'I feel like you're from Nevada'. You need to have a funny reason WHY she's from Nevada, but it's a great way to get playful.
You've also got to get her asking about you, so you can do this a lot of ways. We talk about baiting in Unbreakable, and there is the implied investment video... and I know that in the third week of say hello's homework, there are some really solid exercises and examples. Have a look and get back with some more detailed questions.
Christian