Chocolate flavor can mean many different things. It can be bitter, rich, earthy, acidic and fruity—all qualities that provide various wine pairing challenges. When I was in culinary school, I was always told to drink water with chocolate but there are some very interesting wines that help enhance the chocolate flavor. It is important to taste the chocolate alone first because some chocolates can be complex and bitter and if the wine is not sweet enough, the chocolate will make the flavor sour.