To figure out how and where to start, you've got to know the right questions to ask, and a few tips.
Know what you like. Know your cheese categories and which adjectives best describe them: Fresh cheeses are often mild, milky, tart, and grassy. Good words for bloomies are mushroomy, rich, dense, and creamy. Washed rinds tend to be funky, smelly, strong, boozy, and creamy. Harder cheeses like cheddars, mountain cheeses, and goudas can be described as sweet, nutty, intense, and firm. Use your words and communicate with your server! Even if you don't feel accustomed to talking about cheeses, just try, and you should receive some helpful guidance.
Be open-minded: Cheese is very unlike wine, for example, which often allows for the taster's reliance on past experiences. It's hard to make conclusions on flavor based on milk type (the cheese equivalent for a grape varietal, in wine terms), region, or season. And since there's no such thing as a vintage in the cheese industry-- everyday is a different one, in fact-- it's hard to make generalizations about what a cheese will taste like based on its year, season, or provenance.
Make friends. Ask your server what he or she is especially liking right now. Since cheeses can change from week to week, month to month-- it's the daily vintage phenomenon-- a certain cheese may be especially, unexpectedly excellent. Inquiring about cheese in this manner will give you an idea of the ever-important ripeness factor, which can make or break a cheese.
Be diverse. You want a range of styles on the plate that you design. Hopefully the list will give you some indication as to the age, texture, and flavor of the cheeses. Even if you've never heard of any of the cheeses before, you can safely bet that you'll end up with a varied selection of styles if you choose, say, one cheese that's "nutty and firm," one that's "mild and creamy," and one that's "crystalline and caramelly."
Don't overdo it. Unless you're with lots of people or you want the cheese to be your main course, stick to a selection of three or five.
Drink. Pick some beverages to accompany your cheeses-- wines, beers, or aperetifs will never hamper your cheese-eating experience. And if you do commit some kind of cheese-ordering folly, a drink may even help mask it!
Nora Singley is an avid lover of cheese, and for some time she was a Cheesemonger and the Director of Education at Murray's Cheese Shop in New York City, where she continues to teach cheese classes for the public. She is currently an assistant chef on The Martha Stewart Show.
(Images: Nora Singley)