The Secret to Mastering Your Cocktail Order

“Double Scotch, single-malt.” I tried my best to get the words out confidently, hoping to channel Patrick Dempsey’s character, Dr. McDreamy, on “Grey’s Anatomy.” If a three-ounce pour of single-malt Scotch whisky was good enough for a suave television neurosurgeon, then it was good enough for me, a squeaky 19-year-old with his big brother’s ID at a Manhattan dive bar.

“What?” the bartender shouted at me. I repeated myself, louder but with much less conviction: “Double Scotch, single-malt!” He looked at me funny, turned to his selection of golden bottles and asked, “What kind of Scotch?” When I hesitated, he looked to the guy behind me and said, “Next.”

Recipe: Rob Roy

This first embarrassing attempt at ordering an alcoholic beverage gave me a couple of theories: Either Dr. McDreamy drinks well whiskey or television networks can’t name specific brands.

Like knowing how to order off a menu, ordering a drink is something that needs to be learned. And finding your signature cocktail is an intellectual endeavor — an examination of yourself and your predilections — as much as it is a gustatory one. It has taken me a lifetime to find My Drink, a slow but steady culmination of all the glasses I’ve had before and all the times I’ve anxiously ordered at a bar.

But it’s not just experience and self-awareness that help you find your drink; it’s having the language to tell a bartender what you’re craving, what you like and what you don’t. As with food, “cocktails exist on a spectrum,” says J.M. Hirsch, the author of “Pour Me Another,” which offers tasting words like “refreshing,” “sweet” and “warm” to help you hone your preferences. For Hirsch, using “language that you can taste” is a necessary step toward helping people understand what’s in the glass. It’s also, he says, “a good way to build connections between glasses.” And these connections are, ultimately, what can help you discover a new drink.

‘If you know what base spirit you like, you can’t go wrong with the classics.’

Whenever I have a nightcap of Fernet, for instance, I’m reminded of other amari I’ve sipped — Montenegro, Nonino and Cynar — journaling in front of the Duomo in Crema, Italy. That image of past me stirs fond memories of the many ice-cold Cynar spritzes I’ve enjoyed with friends at Bar Pisellino in the summer. Those bubbles float into my Champagne years, when a colleague and I would go to the underground Flûte in Midtown for weekly Champagne Tuesdays. Another wine I love is sherry, which reminds me of a martini I had at Our/New York, a vodka bar and distillery that became my after-work watering hole for a couple of years (the martini was “dirty” from a splash of sherry). The bar manager at the time, Rustun Nichols, showed me that my go-to martini was actually a 50/50, an evolution from the Bond-inspired Vesper I thought I loved but found difficult to choke down in my early 20s. Now in my 30s, a 50/50 goes down easy.

Your own journey doesn’t have to start at a bar, but a bar — and the person behind it — is a great place to start. While at the Savoy in London, Hirsch told his bartender that he liked Old-Fashioneds and Manhattans served strong — that he liked to be “slapped around” by his cocktail a bit, but that he wanted something more interesting. “What would you suggest?” he asked.

It’s a good question. And it led to Hirsch finding his new go-to: the Vieux Carré, a heady mix of rye, Cognac, sweet vermouth, Bénédictine and Peychaud’s bitters.

Lamar Curtis, a bartender at On the Rocks, a cozy whiskey bar in Hell’s Kitchen, suggests starting simply: “If you know what base spirit you like, you can’t go wrong with the classics.”

On the Rocks is owned by Howard Ostrofsky, who, after retiring in 2008, wanted to establish a global destination for whiskey lovers, not just a local watering hole. A few years later, he opened the bar, where you can find him sitting in a corner a couple of times a week. And it was there, more than 10 years ago, that I started drinking Old-Fashioneds, learning what happens to good whiskeys when you add a little sugar and bitters. They round out at the edges. Then I moved onto Manhattans, a short but powerful phase that helped me pivot back to my original sin: double Scotch, single-malt.

Some whiskey cocktails call for two ounces of the liquor, but a three-ounce pour (a double Scotch) fills a single coupe nicely. Swapping the rye for Scotch in a classic Manhattan, I realized, turns the cocktail into a drier, muskier Rob Roy, named after the Scottish folk hero Robert Roy MacGregor. The Waldorf Astoria is said to have invented the drink; the tradition is to use cocktail cherries to garnish the standard version (with sweet vermouth). For the versions called “dry” (with dry vermouth) and “perfect” (with both sweet and dry vermouths): a lemon twist instead of cherries. Use whatever garnish you like, but I’ve found that the essential oils from a fresh orange peel add a deeper richness that those from a lemon do not.

Over time, one thing becomes clear: When it comes to finding your drink, the devil is often in the details.

Recipe: Rob Roy