The rule is simple
Match intensity with intensity. Match sweetness with sweetness. Match smoke with smoke. That is the whole pairing philosophy, and everything else is decoration.
Chocolate is bitter, fatty, and slightly acidic. Whiskey is sweet, alcoholic, and often woody or smoky. The two want to meet each other somewhere in the middle. If one is much stronger than the other, the weaker one disappears.
Bourbon and milk chocolate
Bourbon is sweet — corn, vanilla, caramel, sometimes a bit of cherry. Milk chocolate is also sweet. Put them together and you get a dessert that is almost embarrassing in how well it works. This is the easiest pairing in the book, and it is not a lesser one. A glass of Buffalo Trace with a square of Cadbury is better than a glass of Pappy with a square of Valrhona, if you are actually drinking and not just showing off.
Rye and dark chocolate
Rye whiskey has spice — pepper, clove, sometimes a green herbal note. Dark chocolate is bitter and sometimes has a natural spice of its own. Rye and 70% dark chocolate is a conversation. Neither one wins. This is the pairing to try when you want to feel like you know something.
Peated Scotch and dark chocolate with salt
This is the pairing that surprises people. Peated Scotch — Lagavulin, Ardbeg, Laphroaig — tastes like smoke and iodine and the ocean. Dark chocolate with sea salt tastes like smoke and bitterness and the ocean. They fit together the way a fire fits a fireplace. If you have never tried this, try it. It changes what you think chocolate is for.
What to avoid
Do not pair whiskey with white chocolate. White chocolate is sugar and fat. It does not have the bitterness to meet the whiskey. The whiskey bulldozes it.
Do not pair cheap whiskey with expensive chocolate. The whiskey will taste worse, and the chocolate will taste wasted. The expensive chocolate is not lifting the whiskey. It is only making the whiskey look bad.
Do not pair whiskey with chocolate that has been sitting in a drawer for a year. Chocolate absorbs everything. If your chocolate tastes like the drawer, your pairing will taste like the drawer.
So what
The best whiskey and chocolate pairing is not the most expensive combination. It is the combination where both parts are doing their job.
Buy a bottle of bourbon you actually like. Buy a bar of chocolate you actually like. Sit down. Take a sip. Take a bite. Take another sip.
If it works, it works. If it does not, drink the whiskey and eat the chocolate separately. Nothing is lost. You are still drinking whiskey and eating chocolate.
