When pairing red wine with chocolate, choose dark chocolate truffles. Chocolatey confections are generally too sweet, as the wine should have a higher sugar content than the chocolate.
Try pairing three different cacao percentages (from 60 percent to 90 percent). The darker the chocolate, the richer and bolder the wine should be. For instance, don't pair 90 percent with a light Pinot Noir. Instead, try it with a rich, tannic Cabernet Sauvignon.
When beginning the tasting, sip the wine first. Then break off a bite of chocolate and let it slowly dissolve in your mouth. Once it's fully dissolved, take another sip of the wine. It's important to taste the wine first and then see how the chocolate affects the taste of the wine. A good chocolate and wine pairing will be obvious.