Valentine's Day Pairings: Bourbon and Chocolate Done Right

Valentine’s Day is the perfect excuse to slow down, pour something good, and enjoy a pairing that feels both classic and a little indulgent. Bourbon and chocolate might sound like an easy match, but when you line up the right styles with the right flavors, the combination becomes something special — the kind of pairing that makes you stop mid-sip and appreciate how well these two worlds fit together.

Bourbon’s natural sweetness, oak influence, and warm spice make it a dream partner for chocolate’s richness. The key is matching intensity with intensity.

Dark Chocolate + High-Rye Bourbon

Dark chocolate’s bitterness loves the bold spice of a high-rye mash bill. Think pepper, cinnamon, and a little bite meeting deep cocoa. The rye cuts through the richness, while the chocolate softens the edges of the spice. It’s a lively, energetic pairing — perfect if you like a little spark. Wilderness Trail Bottled-in-Bond is an ideal pour to pair with dark chocolate. While the 8-year I featured is a little more elusive, it’s 6-Year sibling can readily be found on store shelves.

Milk Chocolate + Wheated Bourbon

Milk chocolate is all about creaminess and sweetness, which makes a wheated bourbon shine. Those soft caramel, honey, and baked-bread notes melt right into the chocolate. It’s smooth, comforting, and almost dessert-like. A great choice for someone who prefers gentle, rounded flavors. You can’t go wrong pairing this chocolate with Weller Special Reserve. The smooth vanilla notes marry sumptuously with velvety chocolate.

Dark Caramel or Sea-Salt Chocolate + Barrel Proof Bourbon

If you want a pairing with some drama, this is it. Barrel proof bourbon brings heat, depth, and big oak character. When you match it with caramel-filled or sea-salt chocolate, the sweetness balances the proof and the salt amplifies the bourbon’s complexity. It’s bold, rich, and incredibly satisfying. The single-barrel products from Knob Creek are found easily on store shelves and make a perfect pair with a dark-chocolate caramel.

Whether you’re celebrating with someone special or treating yourself to a quiet night in, bourbon and chocolate can turn Valentine’s Day into a sensory experience worth savoring. Pick your pour, break off a square, and let the pairing do the rest.