When fixing something like the prime rib I fixed last weekend, there needs to be some thought put into what to fix with it. Mashed potatoes are fine with roast beef, but are they too plain for a prime rib or a
2" porterhouse? In my opinion, yes, unless they’re doctored up to be something else, like garlic mashed potatoes that aren’t too smoothy, more like smashed potatoes.
There are several things to consider when pairing entrees with other items served. When I cook, I usually try to emphasize the main dish, which will often be done outside using wood smoke in some way. I don’t really want the side dishes to compete with it; they should complement in taste and texture. I also don’t want appetizers that become the meal.
Of course, wines served should be selected for how they go with the foods, and, generally, lighter wines should be served with appetizers, but that’s not always the case (everything with wine can be considered rule of thumb only… if you don’t like a wine, don’t drink it). The general rule of red wines with red meats and white wines with lighter meats is decent, but there are some great reds that go well with chicken, and some whites will do well with pork. I’ve heard it said that if you like the wine, that’s all the matters, but this isn’t necessarily the case; taste combinations can make a good wine taste bad.
Acids in wine will cut through through salt, oil and fats in foods, while tannins will balance out proteins and oils, kind of working as a palate cleanser. Trying different wines with different foods is a fun experiment to determine what pairings you like. Starting with a wine that you prefer, try different foods and keep track of what you think of the combinations. You’ll find that a sweet wine with red meat gets REALLY sweet, and sweeter foods will make drier, tannic wines even more so.
I like to start out with lighter wines with appetizers, which doesn’t mean they have to be white; I prefer reds to white wines usually, though not always.
One of the easiest appetizers to serve is cheese. This allows a variety of wines to be served to people’s taste as well as very little prep. I use a cheese safe that keeps the cheese out of the way while it comes to room temperature, which is best to serve cheese. A variety of crackers and bread can be served, and olives and olive oils are good complements to the mix. The heavier the cheese, the darker the wine should be. Bleu cheeses can turn you off of white wines as the flavors tend to clash a bit, but mild cheeses can make you like white wines all over again. Most cheese are not as strong, though, and go well with a variety of wines.
People use to say never to have red wines with chocolate… but try the right combination, and you’ll fall in love with it. Just keep in mind that the lighter, sweeter the chocolate, the lighter and sweeter the wine should be, though the wine should be just a bit less sweet than the chocolate.
A simple dessert that I saw on a cooking show on the Food Network, Party Line with the Hearty Boys, is a creme fraiche/bittersweet chocolate dish. I don’t care for the show or the hosts, but the dish seemed simple. The creme fraiche is heated until it bubbles, then turned down to simmer, and bittersweet chocolate is added in pieces to taste. Stirring is carefully done to ensure that air isn’t added to the mix (no whisking). Once the chocolate melts, pour into ramekins and cool for a couple of hours. The dessert worked well, and comes out tasting like chocolate cheesecake pudding. What I would do next time, though, is add some espresso or something to just kick in another flavor, maybe kahlua. Serving with a mint sprig makes it look very nice, and it goes well with big red wines like syrah, petite syrah or cabernet savignon.
Side dishes should stand up to the entree but not overtake them if you want the entree to be the star. However, that doesn’t mean strong flavors won’t work; rosemary potatoes go very well with prime rib, especially if the seasoning on the prime rib doesn’t clash with it (another good reason to leave the prime rib seasoning neutral). The herb goes very well with both the potatoes and the beef, letting the side dish work well.
Texture is also important, which is why I don’t like mashed potatoes that are creamy in textued with a soft textured meat like prime rib; everything it mushy. A fresh vegetable can fix this, though; crispy asparagus or steamed green beans give a different feel that can make eating the whole meal interesting.
One last taste that can help or hurt a meal is the earthiness of mushrooms. Portabellas are very earthy tasting, and go best with stronger flavors or in very small quantity. Button mushrooms can go with about anything. Wild mushrooms can either be very mild or very strong, so be sure of the taste before using with a dish. Chantrel mushrooms can be used with about anything, as they seem to take on the taste of the dish they’re in.
Take time and try out different things, but not too much at once. Take one wine and try different cheeses, or one cheese with different wines. Try different grades of chocolate with one wine, or one chocolate and several ones. Cook a vegetable to different doneness and try with one meat, seeing if the texture makes a difference to you. Learning how tastes and textures meld into an experience can help elevate your meals to a new level.

Curt,
You are very knowledgable on your wine parings. I whole heartedly agree. To anyone reading that are just starting into wines this is a good start. Also keep in mind that if you are new to wine and prefer sweet it will take a while to appreciate a full bodied red or dry white. The taste will gradually come and expirement is the way to find it.
Todd