Ah, bonjour, gentle reader, on this, the day of love. Forget, if you will, that this feast day commemorates the bloody and violent death of a minor Christian martyr, and try to remember the most important thing of all: you need wine and chocolate, and if you don't have it already, you'd better get moving! Sorry, that was rude. Relax... obviously yours is a relationship built on love and trust; a symbiotic coupling of individuals whose whole is a gestalt much greater than its parts— but hey, a little insurance never hurts, right?
The pairing of wine and chocolate is one of those realms where opinions differ greatly— "Oh, we had Godiva truffles with this Chardonnay, and it was fantastic;" "Nothing pairs with Ghirardelli like 1982 Bordeaux;" "85% cocoa? You gotta go California Cab, man."
Okay, I am usually one of the first to say that when it comes to food and wine pairing, the right wine always comes down to the type you enjoy— don't go for a wine you know you hate simply because its the "proper" thing to do, etc. But chocolate is one of those foods where there is a distinctly right and wrong direction to go in terms of a match.
First, there is a myth that needs to be dispelled outright: chocolate and Chardonnay do not go hand in hand. In point of fact, chocolate and any dry white wine are never going to be friends, no matter how hard you force it, and they should never share the same table, ever. The problem with dry white wine, regardless of its relative "fruit" level, is that by definition it has two distinct characteristics: it is low in residual sugar and light in body. In even the driest of wines, where the fermentation yeasts have eked every last bit of alcohol from the grapes' ample fructose, a little of that simple sugar remains: this is referred to as the wine's residual sugar. Some wines have lots, like most Californian Zinfandel and Australian Shiraz, whose residual sugar level is often high to the point of literal sweetness. Some have practically none, including most French whites and many Italian reds. Because of the nature of our taste buds, if there is not enough sugar in a wine to compete with the sugar in a given food, the wine is going to taste sour— this effect is exacerbated when the wine in question is light bodied, as there is less tannin (the "puckering" compound in red wine and tea) to cover up the unfortunate flavor. All in all, white wine when paired with even the most bitter of chocolates is going to come out tasting like lemon juice and mud— think "brushing your teeth and then drinking a glass of OJ" sort of flavors.
Many reds suffer a similar fate for the same reasons. Indeed, most dry table wine of any kind is going to be a rough match. If you must go dry, go big and bold: Zinfandel, Shiraz, and almost any red from your warmer wine growing regions should fit the bill; in this case, just try to avoid the sweeter stuff like milk and white chocolate. Amarone from the Valpolicella region of Italy is also a good bet— this dry wine is made from raisins, like many dessert wines, so it has plenty of residual sugar, plenty of alcohol, and a big full body which should easily stand up to and compliment an array of chocolaty treats. But still, as long as no one is diabetic or diametrically opposed, sweet wine is the way to go.
Options abound in the realm of sweet wines, given the myriad methods by which it can be made. If chocolate torte is your romantic treat of preference, go with a demi-sec (or 'semi-dry') Champagne. Bubbles and high acid will bring out the more subtle flavors found in an elegant cake, while the lighter structure keeps said pastry from being overpowered. Every major sparkling wine house releases a sweet offering or two— one of my favorites is the Piper-Heidsieck Cuvee Sublime, which is hard to miss for its striking purple packaging. If you prefer your sparklers on the darker side, Italy offers a surprising array of fizzy and fully sparkling sweet reds in various styles. For the flavor of red berries with a full sparkle, you can't top Banfi's Rosa Regale Brachetto d'Acqui. For a similar raspberry/strawberry nose with less alcohol and half the fizz, Fracchia's Voulet Casorzo is beautiful; there is no better pair around for chocolate covered strawberries.
For creamier confections, go with a more traditional dessert wine. The methods by which these sweet wines are produced seem to outnumber the leaves on a vine. However, it may be safely stated that most are very, very sweet and nearly syrupy in consistency. This combination of sweetness and texture is what you are going to seek to compliment the buttery richness of chocolate truffles and other ganache filled treats. Canadian ice wines are a lovely compliment to truffles, particularly those with a fruit flavored filling. By having the grapes freeze on the vine before harvest, winemakers are a allowed nearly maximum sugar content for pressing. The result is a wine of extreme sweetness and density, with surprising acidity and very clean, pure fruit. Unfortunately, the process is very labor intensive and risky, leaving prices in the department of $50 to $100 a half bottle! If you are willing to drop the cash, a few great producers include Inniskillin, Jackson Triggs and Konzelman.
In the south of France on the Gulf of Lion, local vintners produce what is considered by many to be the best wine in the world for chocolate. Called vin doux naturel, these wines are dosed with brandy during fermentation, halting the conversion of sugar to alcohol. Unlike port, which undergoes a similar process, vin doux naturel typically hovers around 15%-18% alcohol, and is made with more well known and noble grape varieties. Chocolate's best friend in particular may be found in the region of Banyuls, which produces a wine of the same name. Banyuls is based on the Grenache grape, renowned for producing the finest wines of the Rhone valley. When allowed to develop to optimal ripeness in the Mediterranean sun, Grenache gives up a concentrated fruit character unmatched by any other grape. Having all the sweetness of port wine with more complex fruit flavors (and lacking that alcoholic burn!), Banyuls is the practically ideal match to any chocolate preparation. Though rarer than most of the previously mentioned wines, most fine wine stores should offer at least one or two, particularly this time of year. My favorite is the Domaine la Tour Vieille, which is full of that quintessential combination of dried and fresh fruit flavors that make Banyuls so unique.
Of course, this is but scratching the surface of the world of dessert wines, but time, I fear, is not on our side. I hope this quick foray will help make your Valentine's Day as sweet as it could possibly be. Whatever the wine you choose, may it be luscious, flavorful, and not nearly as cloying as that last sentence.