Why Pairing Cigars and Whisky Is a Lot Like Sex

"Pairing cigars and whisky is a bit like sex. You want to know at the start of your relationship who's on top—the cigar or the whisky?"

I'm sitting on the smoking terrace in Boisdale Canary Wharf with Ranald Macdonald, founder and owner of the famous London elite hang out, defender of haggis, and Lord of the Isles descendent. I'm supping a Highland whisky and smoking a Montecristo Double Edmundo. At least, I think I'm smoking it. In search of that elusive kick, I'm sucking it like my first cider lolly and all I can taste is ashtray.

Not that I let on. Every time I feel an accusing eye fall upon my oral skills, I issue an "mmm-hmm" and bat my eyelids like a cock-addled porn star.

"There's not one prescribed way to explore someone else's body or for them to explore mine," Macdonald continues, a gob full of cigar, whisky tumbler in hand. "And who's on top or underneath is really for us to decide upon."

Us?

I drop the eyelid thing.

I've been here for three hours and I've sat through jazz, eaten grouse with game chips, and fanboyed over Arnold Schwarzenegger (named The Spectator's "Cigar Smoker of the Year" in 2014 at Boisdale)—until, at long last, we move outside to sample the goods.

The Montecristo, I'm told, is the world's most popular hand-rolled Cuban cigar. It's named after Alexandre Dumas' novel, one of many books read to rollers in cigar plants as a form of communist education (or entertainment, I'm not quite sure which.) The titles of these novels thus became synonymous with a certain batch of cigar and subsequently were adopted as the batch brand name. Romeo y Julieta is another example.

"It's flavour profile is quite rich, medium to full bodied, spicy with a little bit of herbaceous flavour," Macdonald says, before putting his snozz to the cardboard-brown fuselage and taking a long, hard sniff. "And it smells like Samantha Fox's underpants."

I suddenly feel like I'm at The Rotary Club, 2.0.

There's a reason Tatler called Macdonald Britain's "most politically incorrect restaurateur" and in three hours, I've become accustomed to his Macdonald-isms (as accustomed as one can become, I suppose.)

Our first exchange involving his pink socks ("A gift from Idi Amin") was quickly followed by a brief soliloquy on the "great law maker" Napoleon ("He hated frozen foods.") Perhaps it's this right-wing joshing that convinced The Times to interview UKIP leader Nigel Farage at Boisdale in 2013. There's an afternoon I think we can all quite easily imagine.

Eventually, the whisky arrives. Four bottles of golden liquid that seem to sparkle like gifts from the Gods in the terrace's permanent twilight. But getting Macdonald to talk me through the pairings is like shepherding a large cow into a shoebox. Finally, he relents.

"Cigars have just as much complexity as whisky and in actual fact, a lot more work goes into making a cigar than making a bottle of whisky," he says. "They pair well because cigars are high in acidity and whisky is low in acidity, unlike a fruit-based digestif, for example."

But before we pair, we have to taste.

I'm handed an Ardbeg, an Islay Malt Scotch "impregnated" with peat. Macdonald tells me to hold it in my mouth and push my tongue above and below the liquid, as though I'm saying hello ("to a girl from the ball," of course), seven times. Then, and only then, will I get "a feeling for the real flavour"—a smoky, black treacle, thick and molten flavour.

Next, we taste the cigar, pushing the tip against our tongues (which I do, cautiously, in case this is another wind up) and my taste buds fuse with a fuzzy, earthy, almost static flavour. I am instantly convinced that two such flavours with such strong characteristic will simply cancel each other out and I flirt with jacking the whole thing in and diving off the terrace into the darkness beyond …

And then Macdonald starts to pontificate again and this time he's not talking about sex or despots, he's actually talking about cigars and whisky.

This clash of flavours, Macdonald insists, is typically what happens when you stick with conventional cigar and whisky pairings—matching a heavy, peaty Islay whisky, for example, with a full-bodied cigar, such as a Padron 1964. He thinks otherwise. Smoky whiskies, he says, increase the cigar's flavour, they don't compliment it. That's why we've chosen the reasonably tame Dalwhinnie to start with.

Mild but malty with a hint of toasted oak, I hold the amber liquid in my mouth—to get what Macdonald calls "that total mouthfeel of the whisky"—swallow and then let my lips tug on the Montecristo. It's a curious feeling. For two "fluid" elements, the difference in textures is pretty alarming; the smoke is caged in the liquid and much more mild than a none-whisky coated drag. It's almost as though the smoke is being seduced.

We turn to the Glenfarclas, Ten Years Old. The smell of the smoke and Scotch spark a memory in one of Macdonald's friends who's joined us for the evening. "It smells like the Hotel Nacional [in Havana]—a wood-lined elevator and a dirty old bird upstairs who says 'curtains,'" he says.

Meanwhile, in the corner, Macdonald muses: "I can hear my cigars saying to the whisky, 'You're gorgeous.'"

He obviously fancies the Glenfarcis.

Stories begin to swirl around us like the smoke. There's a brief conversation about Macdonald's first trip to Cuba in the late 1980s, a hazy factory-based meeting with a government official, and then something about the time their plane got stranded at an airport and they went off and rented an entire beach. As you do.

I don't have a Cuban tale. But I do have a friend that used to wear a t-shirt with Che Guevara's face on it and when he pulled it up and over his head, on the right amount of drugs, it would feel like I was conversing with the man himself. Thankfully, on the night, I only said that in my head.

The Auchentoshan is next. Single malt and triple distilled, its sweetness against the saltiness of the cigar offers a sweet and sour sensation. This is a complex pairing. I feel like it deserves an equation.

And then we're back to the Ardbeg.

By all (online) accounts, this is the whisky that should pair best with the cigar and in many ways, with the palate near-exhaustion, it does. But it's also an obvious pairing, the smokiness of the whisky and the smokiness of the cigar don't develop against one another, they exacerbate the smoke rather than elevate it.

"Talking about how people like to have sex as a concept for taste, I think this is the equivalent of doing it from behind," Macdonald says, before pausing. "I like the whisky being on top".

And finally, through the haze and constant misnomers, I find something we agree on.