How can you teach a painfully shy child to speak to strangers?

Question: I liked the idea of actually having my seven-year-old daughter learn to speak to strangers. How do I go about something like this when she is too shy to ask for things and sometimes can’t even order her own food in a restaurant?

Answer: You start by starting. Your daughter will be more willing to choose and then talk to strangers when there is a benefit to her. She wants frozen yogurt? No problem, but she’ll need to choose someone and ask where the nearest place is (while you stand close by). She wants to look at puppies? OK, but she’ll first have to choose a stranger and ask where the nearest pet shop is. After she has these discussions, you and she can discuss how the person reacted, why she chose that particular person, was she comfortable with the person she asked, etc.