Re-posted - Photo is a simple cheese board for dessert for about 6 dinner guests
Good cheeses must be treated with respect because plenty of effort, time, and pride goes into making them for you, and the tasty ones are mostly expensive. People always put out cheese and crackers at holidays. Here are The Barrister Family Rules and Tips about serving cheese:
1. The only thing Whole Foods (or whatever it's called now) is good for is the cheese department. That is quite good, and often the Cheese Man is somewhat knowledgeable and will give you a taste.
2. Best grocery cheese dept? Definitely Fairway. Best source of that Irish hard cheese - Dubliner - and of un-aged goat cheese? Costco. We love goat cheese. In Manhattan, Grace's Market has good, unusual, unpasteurized cheeses, and it's a fun shop for foodies. Also, the Grand Central Market in Grand Central Station has tons of tasty stuff including fancy cheeses.
3. Cheese as an appetizer or an hors d'oeuvre? Never. It's not done, not proper except as part of an Italian antipasto and even then only a couple of thin tasting slices. It wrecks the appetite and is too taste-powerful to precede a pleasant dinner.
4. Cheese should always be served at room temp, never cold. If a soft cheese gets a bit melty, so much the better because that's what it is meant to do.
5. Assorted cheeses on a buffet table? Of course. A Cheese Board as an after-dessert savory or, as I prefer, instead of dessert? Definitely.
But served how? Our theories on the topic are below the fold -
Well, for starters they often say to provide around 3 lbs. of cheese per 20 people. A mix of soft cheeses, stinky soft cheeses, Blues (I like Stilton but there are many varieties), and a hard cheese (Pecorino is my favorite, but I do like that tangy Dubliner too). People always enjoy a good mix of unusual cheeses. As a rule, I avoid the rubbery American cheddars which are only suitable for cheeseburgers and grilled cheese sandwiches. If you like orange-colored cheese, Double Gloucester is nice.
To assemble a nice cheese board (cheese platter) to be passed around after dinner, things that are good to include are nuts (eg pecans and walnuts), dried fruits, grapes, sliced fresh fruit (apple and pear), and fresh figs. Some plain water crackers and sliced baguette, and it's done. Many people (including the Chief Cheese Buyer of Fairway) believe that cheese should always be served with choices of jams, honey, and chutney. Red Chili jelly is great. This weekend somebody put out plates of goat cheese logs sitting on pools of apricot jelly with water crackers. Perfect combo. Here are some pairing ideas.

Cheese is not meant to be eaten alone, but I'll make an exception for a Stilton:

What about baked Brie in a puff pastry for dessert, with a side of jam? Great stuff, but I would not put it on a cheese board. It's its own special thing.
Red wine, port, and sweet sherry are really good with that dessert cheese board. Even a sweet Riesling. Stilton + Port were made for eachother.