February 14th, 2014
01:30 AM ET
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Ray Isle (@islewine on Twitter) is Food & Wine's executive wine editor. We trust his every cork pop and decant – and the man can sniff out a bargain to boot. Take it away, Ray.

This Valentine’s Day it’s very important to keep in mind that there’s a paranoid conspiracy floating around our world to the effect that red wine goes well with chocolate. This delusion isn’t quite on the order of believing that the moon landing was a hoax, but it’s pernicious nonetheless.
Here’s the deal. Anything you eat that is sweet (e.g. chocolate) is going to make a dry red wine taste more sour and astringent than it already is. So, basically, if you give your date a nice box of chocolates and then serve her (or him) a big ol’ glass of Cabernet, the reaction is likely to be along the lines of “bleah!” And I’m here to tell you, “bleah” is not the word you want to hear at the end of the evening on Valentine’s Day.

So, what to serve with those Godiva truffles you shelled out for? The options are numerous, but sweet wines and richer spirits are definitely high on the list. You could, for example, pour your loved one a nice Port—premium ruby Ports (and similar styles), such as the plummy, complex Graham’s Six Grapes ($19) are excellent with dark chocolate; for milk chocolate, head towards a tawny port instead, which gets its nutty, caramelized character from extended barrel aging. A good choice: the graceful Taylor Fladgate 10 Year Old Tawny ($33).
Even better than Port, in my opinion, is Madeira—it has a citrus-rind tanginess that works particularly well with dark chocolate. Buy the real stuff, for instance the toffee-scented Blandy’s Five Year Old Malmsey ($25) or for a few dollars more (and if your main squeeze is a history buff) the slightly less sweet Rare Wine Company Historic Series Boston Bual ($49), whose flavor suggests candied orange peel and toasted nuts.
Another option is to skip wine entirely and head towards spirits. The vanilla-caramel notes of a good aged rum will complement chocolate very well, particularly milk chocolate. Some fine possibilities include the luscious Ron Zacapa Centenario 23 ($40 or so), the lightly fruity, spicy Botran Solera 1893 ($35), or, if you can find it and you really, seriously want to impress your date, the complex, silky Facundo Paraiso ($265), a blend of rums aged between 17 and 23 years from the Bacardi family’s private stocks.
And if you really just have to have a glass of red with your chocolate, well, here’s how to make it work. The key is to pick a high-quality dark chocolate with a very high cacao content and not much sweetness.

Domori, for example, which is owned by the Illy coffee group, produces a number of bittersweet bars in the 70-75% cacao range, from different origins (many other top producers do as well). With a substantial Napa Cabernet, for instance, this combination really does work. It may even get your date to say “wow” instead of “bleah.” And that’s really the whole point, isn’t it?
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Eat This List: 5 meals for single people – Jean Grae
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Filed under: Chocolate • Content Partner • Food and Wine • Sip • Valentine's Day • Wine

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