Wine and chocolate. It sounds like a match made in heaven, but quite honestly, the pairing rarely lives up to expectations. Why? The natural tannins in red wines fight with the chocolate, and the sweetness of the chocolate make the wine seem more tannic - a visious cycle.
The solution? Pair dark chocolate with sweet wines.
Though Americans turn up our nose at sweet wines, the truth is they can be heavenly when part of the dessert or cheese course. It has always struck me as odd that the country that consumes Coca Cola (at 10 cubes of sugar per can) won't touch high-quality dessert wines. I'm not talking about table wines with high degrees of residual sugar - please leave those on the bottom shelf at the wine shop where they belong. For pairing with chocolate, turn to wines made as dessert wines.
But before we get to the wines, let's talk for a moment about chocolate. Because Mmmmmm.
The Ideal Chocolate:
While most of the chocolates you see on the market, especially around Valentine's Day, are often milk chocolate, white chocolate, or cream-filled, I recommend pure chocolate bars - the darker the better. Those with almonds also work well, especially with the wines I've recommended here, which are known for their nutty characteristic (called Rancio by wine collectors- our wine geek word of the day).
Fortunately for all of us, there has been an explosion of artisinal, single-source chocolate producers in the past decade. Look for Dandelion Chocolate ("bean to bar" chocolates), Dick Taylor and many, many others. Melissa Clark of the New York Times, published a good article last year listing 13 of her favorite gourmet chocolate producers which includes these two favorites of mine plus 11 others. I also recommend her article on chocolate tasting techniques - we've found the approach she describes to have significantly elevated our tasting experience.
The Ideal Wine:
And now for the wine - the crowning glory in the whole affair! While some have found pleasure in pairing dark chocolate with highly extracted/high-alcohol table wines (the reds from Rombauer come to mind, as do those from Frank Family, Biale, many Lodi Zins...) I skip this intermediate step in favor of wines specifically designed to pair with dried or baked fruits, nuts and dark chocolates - fortified wines such as these:

Tawny Port
Port is the term for a fortified wine from Portugal's Douro region. Wines made in a similar style that are NOT from Portugal can't use the term "Port" (such as the one from the fun and jovial winemaker, Andrew Quady, who calls his Port-style wine "Starboard"). But the real thing is sufficiently affordable to justify a trial purchase. Look for a basic Tawny without any age indication for a deliciously satisfying and affordable Port. Passagem Tawny Port $19.99/ 500ml bottle.
All ports are part of the family of fortified wines - wines whose fermentation was stopped by the addition of a grain alcohol, thus preserving the grape's natural sugars before they could be fully fermented into alcohol while also raising the alcohol level in the finished wine.
Ports are generally 18%-20% ABV, and because they are so rich on the pallet and high in alcohol, they're served in smaller pours than regular wine. Most producers of high-end stemware have a line designed specifically for Port, and if you have sufficient storage space, Port glasses make a nice addition to your stemware collection. Otherwise, use the smallest wine glass you have and pour less than half full - about 4 ounces. Ideal serving temperature is "Cellar temperature", or about 60-65 degrees.

10-Year Tawny
Aged in smaller oak barrels than is a Vintage Ruby port (aged in huge, often century-old wooden casks), Tawnies age more quickly due to the higher ratio of wood-to-juice. A ten-year tawny like this one (left, above) was aged in oak for ten years, while the regular Tawny (right, above) still shows its youthful color and brighter fruit flavors. But it's color is not the only difference - the older wine exhibits greater nutty, spice and Sherry-like notes that go quite well with chocolates of all styles. Passagem, 10-Year Tawny, $33.99
Rivesaltes Ambré
Rivesaltes is a town in the South of France and a demarcated wine-making area known for sweet wines - this is one of six types produced there (Rosé, Grenat, Ambré, Tuilé and Hors d'Age). The Ambré style sees at least two years of oxidative aging that yields a deep golden hue upon bottling, and which darkens further with bottle age. The flavor is distinctly nutty with citrus peel spice notes. ~16% alcohol. Read more about this fascinating place here at - Domaine Fontanel 2008 Rivesaltes Ambré, $25.99
Banyuls
La Cave de l'Abbe Rous is a co-operative of small growers from the best sections of Banyuls, producing wines at the highest quality level for the appellation. Among the best dessert wines I've tasted, but also one of the most obscure (the vast majority being consumed within France), the wine is similar to an aged Tawny Port in both alcohol (~20%), aging (9 years in cask) and flavor profile (nutty with a ginger and spice top note). Read more about it here - 2003 Banyuls Grand Cru Joseph Nadal, $47.99
Whatever wine you choose to pair with chocolate, I encourage you to experiment with something new - new chocolates, new wines, and maybe, even new friends to share them with. Physically distanced, of course, as long as our health requires it, or even virtually if necessary!
About the Author: Dave the Wine Merchant has been involved in wine for four decades. He now enjoys discovering and sharing global wines that stretch the imaginations of curious wine lovers and encourages them to "discover a new favorite!"