eGullet is one of those great websites that I don't visit as often as I should, and where I always spend way too much time surfing through when I get there. On my last visit I found a posting by Steven Shaw, a James Beard Award-winning food critic, that's chock full of tips about getting the best a restaurant has to offer, starting with those all-important, impossible-to-get reservations. It's an excerpt from his new book, Turning the Tables: The Insider’s Guide to Eating Out.
On reservations: Every night at a popular restaurant is like an overbooked airline flight. . . It's that careful balance between genuine enthusiasm, flattery, and exhaustion that makes extra seats magically open up.
On getting treated like a regular: Although each individual meal at a top restaurant should be excellent, most seasoned veteran diners take the long view. To them, eating a first meal at a restaurant is like a first date: it's a preview that helps you decide if you're going to want a second date.
On ordering: There's no way to become a food or wine expert overnight, or even in a year. But you don't need expertise. All you need is enough confidence to ask questions.
On the wine tasting ritual: The wine service ritual is romantic and entertaining, but it's mostly pragmatic. The main goal is to determine whether or not the wine is "corked." . . . The wine service ritual is not, however, intended for you to see if you like the wine.
On getting good recommendations that aren't just up-selling: the more specific your questions are the more likely you are to take the server off script. "What's good?" is not nearly as effective as "I have X, Y and Z preferences; what's good?"
I think I'll be trying a lot of this advice out soon. Check out the comments too, there's a ton more info and conversation there.