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New Food and Wine Pairings:
Sweet Wines + Chocolate
I'm a person of strong opinions, which I frequently take pleasure in expressing. But when it comes to wine, I try to exercise caution with that tendency, because I feel that the appreciation and enjoyment of wine is a very personal experience that should only be sparingly pre-empted or tainted by 'expert' advice. However, very much like art and design, even among variations of tastes, styles, and approaches, there are still some universal, often fundamental, 'rules,' if you will, about which elements work together and which ones frankly do not. Red Wine and Chocolate do not work together.
I can't say enough how sick and tired I am of hearing about "red wine and chocolate" as if they were some match made in heaven. Well, it's B.S.! The emperor isn't wearing any clothes, folks! And if you really think so, then brace yourself while I spew my strong opinion to the contrary.
Apart from the fact that very few, if any, wine professionals would agree to such a match, allow me to explain why the two don't work together. It all boils down to dryness and acidity, two of the handful of elements comprising a wine's style that dictate how it's experienced on the palate and how it works when paired with food. Dryness refers to the amount of sugar left unfermented, referred to by professionals as residual sugar. Red wines of quality have no residual sugar, and so are completely 'dry.' Without this sugar, a wine is rendered thin and flat on the palate when paired with the sugar in chocolate (or any sweets, for that matter). As for acidity — well, it doesn't play well with anything sweet. Salty, yes; but not sweet. (Which is another reason why champagne is a terrible pairing with desserts, because, compared to most full-bodied red wines, it has even more acidity.) The take-away message here: an acidic drink does not go with a sweet food; avoid it like the plague and your tongue will thank you.
So if not Red Wine, then what does work with Chocolate?... Port!
You want a match made in heaven? Then try pairing that chocolate with an aged tawny port, and you'll experience a true synergy — the likes of which dry red wine simply cannot even begin to approach. Port has residual sugar; as I explained above, that's crucial. What's more is that the tawny variety has toffee, caramel-like, nutty qualities that compliment chocolate (and chocolate desserts) beautifully. But honestly, even a ruby port will work; the point is the fullness of the wine, and the presence of residual sugar. Other options to pair with chocolate are the light, sweet dessert wines made from muscat/moscato (Italy, California) as well as rich, nectar-like ice-wines (Germany, Canada, and some northern Washington State). The point, again, is sugar! The wine must be sweet! Oh, and if you think that sweet wines must be tacky, cloying, or in any way related to that abomination called White Zinfandel, then I invite you — implore you — to experiment with the dessert wine offerings at any quality-driven, small, neighborhood wine merchant. Simply go in and ask for a recommendation from one of the retail staff. There's an entire world of sweet wines out there that's nothing short of transcendent! 
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