If one investigates the time-honored pairings of food and wine, there will be scant mention of chocolate, for, perhaps along with the formidable egg, chocolate is probably the most popular food item to unfortunately present severe challenges to wine. The problem lies in two of its characteristics: sweetness and bitterness. Sweetness in food diminishes the perception of the sweetness in the wine paired with it. Thus, if you are preparing a braised chicken with raisins, the sweetness of the fruit will cause the wine to taste drier. This consequence becomes very pronounced with sweet desserts, and has produced the useful rule of never serving a dessert that is sweeter than the accompanying wine. This applies to chocolate.
 
Conversely, bitterness in food accentuates the sense of bitterness in wine. Accordingly, if you taste a crisp sauvignon blanc, then take a bite of arugula salad, followed by another swallow of the wine, you will immediately detect a lean austerity and slightly bitter aftertaste in the wine. The complicated nature of chocolate lies in its combination of the bitterness and sweetness. The list of suitable companions is short:
 
Port

This marvelous dessert wine is made by adding brandy to the wine at a point in fermentation that halts the further conversion of sugar to alcohol, leaving a meaningful level of residual sugar in the wine. Vintage Port from a great year, with its viscous body, depth of sweet berry and plum fruit, and earthy, chocolate-like finish, can be a profoundly sumptuous accompaniment to a fine chocolate. Other less-expensive versions of port that go well are Tawny and Late Bottled Vintage ports.
 
Pedro Ximenez

This is a very sweet and thick sherry made in the Andalusia region of Spain. After harvesting, the PX grapes are laid out in the sun for several weeks, where the dehydration concentrates the sugars before the grapes are fermented into wine. The result is a somewhat syrupy sherry with a flavor of roasted prunes, but one that, if well made, is balanced with an edge of alcohol and underlying acidity that keeps it from being cloying. These are increasingly available around the U.S. and I highly recommend those made by Alvear and Lustau. A short cut to this experience is just to pour a little over some fine chocolate or coffee ice cream. This is seriously good.

Cabernet Sauvignon

A rich and powerful style of California cabernet sauvignon can be a luscious match with a chocolate truffle that is not too sweet, and particularly one that has a cherry or strawberry inside. Obviously, other forms of this combination would work besides truffles, but cabernet sauvignon usually has a chocolate/coffee/tobacco element that, along with its fruit-forward nature and full body, frequently pairs well with chocolate and berries.
 
Outside these choices and a few wines like them, a French Maury or perhaps even an Italian Amarone, your chances of pleasure with the wine in the context of chocolate are remote, so don’t bother. Try the Port and Pedro Ximenez; you just may discover a new passion.