Be more experimental
Always picking the same wine with dinner is the vinous equivalent of having a pamphlet with two recipes on it and trying to call it a cookbook. You’ll likely have the most success with food and wine pairing in the same manner that you gain success in cooking -- by not being afraid to experiment. There are roughly 10,000 different fine wine grape varieties being made into wines. Italy alone has hundreds. By being a fearless taster, you’ll not only seriously up your wine and food pairing game, but you might just find some new favorites.
Do what you like!
Unless you’re cooking and pouring for a gathering, or are super into the art of raising wine and food pairing into borderline artistic expression, the most important rule of matching up food and wine is to start with what you enjoy, even if your selection bucks the rules of food and wine pairing altogether.
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Joe Roberts is a Certified Specialist of Wine, and can regularly be found roasting the wine world's sacred cows at 1WineDude.com. Follow his wine recommendations and musings: @1winedude.