Chocolate’s Latin name is theobroma cocoa–food of the gods. Chocolate may be refined into many different styles, degrees of sweetness and percentages of bitterness.
When pairing desserts and chocolate, I try to avoid overly sweet desserts, and use the rule of thumb that the wine should be sweeter than the dessert.
My favorite pairing with chocolate is Port wine. There is a magical symmetry of a sweet Port that compliments the bitterness of chocolate. If the chocolate has fruit elements like cherries or raspberries, I lean toward a Ruby or 10 Year Tawny Port. If the chocolate has a higher percent of cocoa, I lean toward a more complex Vintage Port. With caramel and nut elements with chocolate, I recommend a sweet Cream Sherry or sweet pedro ximenez from Montilla-Moriles in the south of Spain that have nutty and maple syrup qualities.
For a domestic option I like late harvest zinfandel, especially the one from Dashe Cellars (www.dashecellars.com) from Sonoma’s Dry Creek Valley. It has jammy raisin qualities with subtle notes of baking spice that are perfect for chocolate.
I prefer not to pair red wine with chocolate because the bitterness of the chocolate can throw off its complexity. If you prefer red wine over sweet wine, a fruit forward full bodied jammy red will stand up to the chocolate. Reds that pair well with chocolate include fruit forward Napa Valley Cabernet Sauvignon and ripe jammy California zinfandels. Red wines with massive tannin structure should be avoided.