Now I've...had...the time of my life....no, I've never felt like this before... wine and food edit
We have all had those pairings where 1+ 1 = 5. Lightening strikes, birds sing, fireworks go off, someone (likely me) bangs their fist on the table and exclaims "hot damn!". Conversely, we have all let blundering pairings pass by unremarked upon. How does one hit more dingers than duffs? I have no idea, but I can tell you how I do it. *wink*
This lift happens because the structure each partner brings is well balanced by the other. It's memorable, because there is a clear star. Stay with me; I promise it will make sense. Firstly, pairings are about structure, and intensity to start. Zero points will be awarded for style, if the structural foundation isn't there. Does it matter if her toes are pointed or fingers extended if she's still on the ground? See? You get it!

When I look at a menu to write pairings, my second question is always what is the star of each dish or the focus of the evening overall. If it's a menu based of a series of luxury ingredients (truffles, caviar, abalone) and the point of the dinner is to highlight these components, then I will choose Patrick Swayze wines. Solid supports. Wines that are a bit more modest, that bring the necessary structure and always shine a spotlight back on the star.
“You can smell a turd a lot more easily in a bed of tulips than in a garbage dump. ”
When I'm pairing against truffles for example, I never choose an earthy wine. Why you ask? Because you can smell a turd a lot more easily in a bed of tulips than in a garbage dump. For things that are earthy, I love bringing high toned fruit to make it dynamic! The human nose/brain dialogue is fascinating....I imagine my brain sees my nose as a rambling toddler....and after a bit, as soon as it has a sense of what it's saying, tunes it out. Nose-blindness. By having dynamic pairing, each bite / sip keeps communication open and really allows for an extended sensory conversation.
Now what if the dinner is built around showcasing some really special wines, the Jennifer Greys if you will? The menu becomes more of a collaboration. I put forward some style, intensity and structure guidelines and then let the chef go to town. When making the wine the star, I've found pairings more successful when the focus of the food is on higher quality ingredients and refined techniques vs a multitude of components and busy flavours. Keeping food simple lets the wines shine more brightly. Is there a measure of trial and error? Absolutely! Especially when the wines are coming from a private cellar and I don't get to taste them before the main event.
Part of learning is practicing, failing, practicing more, failing more and eventually you nail it. If it makes you feel better, most people can't tell the difference between great and excellent, so be bold! Go with the crazy pairing. I promise you nobody will die, unless the crazy pairing is arsenic...then they might.