Flavor pairings should either be in one of two forms, contrasts or compliments. Look at the flavor components in the brandy in much the same way you would a wine and then decide what direction to take. If the brandy is particularly sweet maybe something spicy, fatty, or salty. If its somewhat acidic think of something that is also acid to bring out the other elements or something sweet to balance that back out. If you compliment flavors it sort of tunes out the white noise to draw attention to subtle flavors and if contrasting flavors are chosen they add to each other in a sort of harmony.
You might take a look at classic brandy cocktails (sidecar, etc.) and work backwards from there, taking those flavors and making them foods instead of liquids.
Chocolate is appreciated in much the same way as wine so you make put some thought into the chocolate you pick as well.