I had the interesting experience over the weekend of being the guest wine speaker for an all-chocolate brunch that the immensely talented Andrew Shotts, of Garrison Confections in Providence, put on at the James Beard House.
Generally speaking, I think chocolate and wine go together miserably. People seem to want to believe that a big intense Cabernet or Zinfandel will go wonderfully with a hunk of high-quality chocolate; in fact, they want to believe it so much that they ignore what's going on in their mouth, which is usually the chocolate obliterating the taste of the wine. Dark chocolate (the chocolate worth eating, I think) is tough: it's intensely flavorful, it's bitter, sweet, fruity, complex, and also fairly alkaline. It can work very nicely with sweet wines—Bual or Malmsey Madeira is the absolute, top-o-the-heap, A+ chocolate-pairing wine, in my experience—but for dry wines the stuff is usually a disaster.