Miss Manners says that guests (which you are when the guy is paying) should always order from the middle (price range) of the menu. I agree, though, if you just feel like a sandwich or salad or whatever, order it, even if it is the cheapest thing on the menu. As far as alcohol, I *think* the proper etiquette (by the book) is to follow the host's lead - if they order alcohol, you can, but if they don't, you shouldn't. However, if it's someone you're thinking about seriously dating, and you are going to expect that you should be able to order alcohol on their dime every time you go out, I guess go ahead and order it, so the person knows what they're getting themselves into. Just be prepared to pay for it yourself if need be, such as the anecdote above.
