One thing I like to do to practice speaking with someone I don't know is ordering food at a restaurant. When the waitress comes to take your order, I ask her what she likes to get. Sometimes she'll blurt something out she really likes, sometimes she asks what you are in the mood for. I try to have two items picked out to choose between, then ask her questions about the food like "What's the sauce like?" or "So you really like this?"(can be serious or joking--you can practice your comfort level this way.)
Of course, servers are trying to please you, so this is just for practice--but it can be fun. Often, the server is an HB too, so that makes even better practice for flirting or a bit of C&F, without having such an investment that you feel like you blew it. As long as you aren't in a big hurry, this is a good way to practice because you can count on the girl to engage you in conversation because she wants a good tip.
-Klats