by Risa Nye

Quick word association: Valentine’s Day.

Did you immediately think of chocolate? Big heart-shaped boxes full of dark and delicious chocolates nestled in crinkly brown paper? Or perhaps you thought of beautifully decorated truffles with fillings that burst with intense flavors.

But did you also perhaps think of wine? Because wine and chocolate can be a real power couple if the match is a good one. And Valentine’s Day is as good an excuse as any to experiment a little with matchmaking.

I was recently invited to meet with Steve Shaffer, owner and wine maker at Urban Legend Cellars in Oakland, to do some experimental pairings of wine and chocolate. I said yes immediately. Who wouldn’t?

I didn’t think this experiment in choosing compatible pairs would have any similarities to speed dating, since one should take one’s time in evaluating each pairing. Good matches can take a while to discover and evaluate. You can’t hurry these things.

Shaffer’s first tip for determining a good match: It’s best if one half of the pair is sweeter than the other, which is often the case with human couples too. With wine and chocolate, however, the wine should be the slightly sweeter half.

For our tasting adventure, the contestants were lined up next to each other: a row of attractive bottles of wine, and a dazzling display of alluring chocolate in the form of truffles, chocolate-dipped strawberries, cake, budino; white, milk and dark chocolate chips; and chocolate covered cherries, blueberries and cranberries. Our work, if you can possibly even call it that, was cut out for us, courtesy of Shaffer and several members of the East Bay Vintner’s Alliance.

I learned that with wine and chocolate, you can tell fairly soon if the stars are aligned and the couple has a rosy future together; and sometimes it’s best to keep looking for a more complementary match. Some of the pairings lit up the sky, while others were compatible but less dynamic. If the pairing wasn’t meant to be, we tried to figure out why without taking sides.

Our first pairing: from Rock Wall Wine Co., a Sparkling Grenache Rose and a luscious strawberry dipped in white chocolate. This wine has around .5% residual sugar. We broke our first rule of relationships by pairing a less sweet wine with those strawberries, but we decided that the tartness of the berries mitigated the sweetness of the wine. This wine didn’t work as well with the milk chocolate we tried with it because it lacked any tartness. In general, Shaffer recommends pairing sparkling wines with lighter chocolate.

Next up: Urban Legend’s 2011 Late Harvest Viognier paired with the chocolate budino from Chef Craig DiFonzo at Oakland’s Lungomare. This wine has around 6% residual sugar. Shaffer describes it as a “beautiful sweet white wine.” We also tried this wine with a Ginger Truffle made by NK Chocolates of Alameda. The wine has “caramel and vanilla notes” and paired well with the creamy caramel and sea salt budino, which I had a hard time not devouring in its entirety. This was a great example of how the wine and the chocolate should build on and complement one another—which is true of any loving couple. This pair definitely has legs.

We followed this delicious pairing with Dessert Zinfandel (Port-style), a fortified dessert wine by Lusu Cellars that Shaffer described as “less tawny and more of a brighter-note port.” This was less sweet than some of the other wines, with around 3% residual sugar. We paired it successfully with milk chocolate and the white chocolate-covered strawberries, which are less sweet. Again, the acidity of the strawberries was a factor in making a good match with this wine.

Next, we tasted an NK Champagne truffle with the Late Harvest Zinfandel by Dashe Cellars. This wine was definitely sweeter than the truffle and chocolate covered cherry we paired it with, and would be a good match for any type of chocolate. This wine, with around 10% residual sugar, is in what Shaffer describes as “the safe zone”: you can pair it with the very deepest, darkest chocolate. I can say without any reservation that this is one mighty sweet wine and it can stand up to the most robust chocolate any day of the week.

(As we progressed through our tasting experiment, Shaffer pointed out that dessert wines typically have a higher alcohol content than other wines. Because we both had other activities planned for later in the day, we made prudent use of the—no elegant way to put this—spit bucket. For the record: no dribbles, no ricochets.)

We then moved on to some wines that were less sweet to see how well they paired with our still abundant array of chocolate items. Among the classic examples of wines that have less residual sugar but are still compatible with chocolate are Zinfandel, Petite Sirah and Syrah.

Urban Legend’s Gioia Locale (a Zinfandel/Petite Sirah blend), with its notes of vanilla, plum, and a little spice, went well with the chocolate covered cherries and blueberries we tried. Shaffer points out that this wine has “an oaky nose and some smoky notes” as well. It’s a drier wine than the others, with just a hint of sweetness (less than ¼ of a percent residual sugar). The zinfandel in the blend makes this wine a good choice to pair with chocolate.

We tasted the 2011 Urban Legend Syrah next. Its brightness and fruitiness went well with the chocolate-covered blueberries because of its blueberry notes. But when paired with a chocolate truffle, the acidity and bitterness came out and the chocolate dominated. We thought it should be paired with something less rich than a truffle (like the chocolate-covered fruit, for example).

We definitely had fun with this exercise in matchmaking. As Shaffer said, midway through our tasting and discussion about notes and noses, “Too many people take wine much too seriously. If you’re messing around with wine and chocolate, you can’t be serious—you can only have fun!”

In matchmaking, you could say that there’s a lid for every pot and a wine for every chocolate. Finding the right match may take time and some experimentation, but the rewards are sweet.

Urban Legend Cellars (Steve and Marilee Shaffer, owners and winemakers) is located in Oakland’s Waterfront Ironworks District at 621 4th St. Tasting room hours: Fri-Sun, 1-6 pm.

Risa Nye lives in Oakland. Her articles and essays have appeared in the San Francisco Chronicle, The Monthly, Hippocampus magazine, and several anthologies. She writes about cocktails as Ms. Barstool for Nosh at berkeleyside.com and about other things at risanye.com.