Another way to work on those interactions would be to hand over store/restaurant transactions whenever they crop up and you're with her. Even if they're not cash transactions, your child can do everything except sign the slip (she could also enter a PIN if you're doing it that way, but I wouldn't advise it!). And in a restaurant, she should be ordering her own food.
Yes. She is very slow to become comfortable with this kind of interaction, but I've learned she will do it when in a group of her friends who are doing the same thing, so that's where we are pushing it right now. She's also still discovering that she has desires that can be satisfied by spending money - I have to point out that if she wants a hat, and has money, she could solve this.
I was the same way - I first bought something for myself in late high school, and didn't do it routinely until the end of college. I'm not sure why it's so slow for her, but it isn't for her sister, so I'm pretty sure it's just an individual difference. DD8 has been placing her own restaurant orders and fluently spending birthday money since she was 3 or 4.
