Rules of Thumb

• When choosing wine and chocolate for pairing, strike a balance using sweetness as your measuring tool. In general, choose an artisanal-quality chocolate that is no sweeter than the wine. Usually, this means choosing a chocolate with a very high percentage of cacao, or a late-harvest wine with significant residual sugar. Choose your wine savvily, also. For example, when choosing a Cabernet, opt for a bottle with "dark," "deep-roasted" and "toasty" notes, which will pair well with highlights in the chocolate's flavor profile.

Ready-Made Pairings

• To take the guesswork out of pairing, look to the experts. Some high-end chocolatiers offer bars tailor-made to complement various varietals, matching the natural tannins in the chocolate to corresponding tannins in the wine it's designed to accompany. Some extra dark chocolate bars -- of at least 72 percent cacao -- are custom-made for Cabernet. Look also for those high-cacao treats that contain almonds as a Cabernet-friendly choice.

Beyond the Cab

• If you're not married to the idea of Cabernet, you may be happier choosing a different varietal. According to Sara Schneider, the Wine Editor at Sunset Magazine, Cab isn't necessarily the best choice for a chocolate pairing. Though there is often a cocoa note to the structure of the wine, Cabernet Sauvignon has a highly tannic "backbone" that's highlighted by juxtaposition with chocolate's sweetness. The wine's harsh tannins can seem overtly astringent next to chocolate, disrupting the pairing. Instead, Schneider suggests softer Merlots and Zinfandels, which have far lower tannin levels.

Play With It

• As with all things wine-related, there is no "right" or "wrong" approach. Once you understand the basic principles, an oenophilic endeavor is entirely beholden to the tastebuds of the oenophile. For example: move outside the realm of pureblooded Cabernet Sauvignon, and you'll find a world of blends. Many blends have lighter tannins, and can thus tolerate a wider variety of chocolates than pure Cabernets. Pick up a variety of chocolate styles, too, to experiment with the pairing. Milk strawberry, vanilla bean, salted caramel and sea-salted chocolates can each bring a unique offering to the palate. Sure, you can seek wines that display the same flavor notes as the chocolate -- nutty, toasty, caramel and mint -- but also look for compelling contrasts. The key is to revel in the process of discovery.