Chocolate is genuinely hard to pair, and anyone who tells you otherwise hasn't tried it with a dry red.
The bitterness and fat in cocoa flatten most wines and make tannic reds taste harsh. What works is sweetness and depth: LBV or tawny Port, Banyuls, Maury, sweet fortified reds. Dark chocolate is the easiest to match. Milk chocolate needs a lighter touch, and white chocolate is best left alone with a coffee.