A Cigar on the Roof with You

Small pleasures like ghosts in a cloud of smoke

Illustrations by Syan Rose

TThe first time was on the roof, and so every time after had to be on the roof, even though it violated the building’s bylaws. Fortunately it was raining in our rainy town, so we were alone up there, under a big purple bruise of a sky. It took a few small inhalations to get the thing lit, and then he passed it to me, casual and two-fingered. The tip glowed orange, a flare in the drizzly evening draped over the city. I brought the cigar to my lips, sucked in the nutty, full-bodied essence of it, which curled unhurried around my mouth, then whooshed out into the night like a phantom.

That night, we did nothing but smoke, and drink, and talk, my love and I. His history, my history, our history vanished into the simplicity of the moment. A rapidly diminishing bottle of Rittenhouse Rye marked the passing minutes. The smoke made an electricity between us, the conduit for an intimacy that felt like inhabiting the exact right place in the universe, at exactly the right time. Infinite possibility seemed to open up before us. We talked about the future: where we would live, the preponderance of dogs we would have, and how, above all, we wanted always to be able to retreat to a rooftop, or a space like a rooftop, to smoke and drink and talk about the future, all the futures we saw for ourselves.

That was the first time, and I think every time since has been in futile pursuit of its perfect stillness. A few months prior, my partner’s friend had given out sets of five Macanudos as wedding souvenirs to his groomsmen, as well as a humidor, double-bladed guillotine, and butane lighter: everything you need to start in on an ill-advised hobby. This was less of a novelty to my Texas-raised boyfriend, for whom cigars represented an infrequent but mundane aspect of certain social occasions. He’d grown up watching his friends’ parents light one up on muggy summer nights after football games and backyard barbecues. Not so his Yankee girlfriend, a product of the big-state, hyper-regulatory Northeast. My hometown was one of the first American cities to ban tobacco products in bars and restaurants.

If that weren’t enough to deter me, my parents are both doctors, and not the hip, permissive kind. The list of activities forbidden to me in childhood included all downhill winter sports, jumping on trampolines, even thinking of climbing onto the back of a motorcycle. In particular, my father’s field of passion and expertise is smoking cessation and anti-tobacco advocacy. I was raised implicitly to believe that smoking was a sin, with a moral karma akin to that of theft or adultery. In my family, we wrinkled our noses at the sight of the poor, addicted sap engaging in this archaic pastime, definitively linked with devastating health consequences decades ago. But then I went to college, and every fourth or fifth time my friends and I went out drinking, in the wee hours of the night, they’d step outside and brandish a cigarette, sharing it like a confidence, or the password to a secret club. Of course, I wanted to be in the club. When I moved to Seattle, I found a social scene mostly void of smoking, so I didn’t bother, either. I didn’t miss it.

My parents are both doctors, and not the hip, permissive kind. I was raised implicitly to believe that smoking was a sin, with a moral karma akin to that of theft or adultery.

UUntil that damned cigar. Like much of what I’ve loved in life, cigars are addictive and toxic. Unless you’re the one smoking, they smell terrible. Cigar smoking is associated with an increased risk of oral, esophageal, and lung cancer, as well as heart disease. The deeper you inhale and the more frequently you smoke, the greater these risks. But to my chagrin, like Rufus Wainwright once said: everything I like’s a little bit harmful for me. A twinge of guilt always attends the act of smoking for me, and I’m certain that’s part of why I like it.

But it’s not the only reason. I like that, unlike with a cigarette, you aren’t meant to pull cigar smoke down the throat, but rather hold it in your mouth like a wine, then release it, nice and easy — an accidental meditation. Cigarettes make me cough and weed makes me sleepy, but cigars bring on a slow, steady high, the advantage of indulging only in scattered instances, without any built-up tolerance. I like the give-and-take rhythm of passing a cigar back and forth, the grace of an outstretched hand accepting its turn at a shared gift. I like partaking of a tradition historically and even now gendered male. Think of the most iconic cigar-lovers, on and off the silver screen: Pacino, Schwarzenegger, Eastwood, Churchill, Che. Not quite my personal idols, but all exemplars of a swaggering machismo that I don’t mind imitating, even in half-parody. Not that I’m the first or only woman to embrace cigar-smoking as a form of gender play; Rihanna, Dita von Teese, Sigourney Weaver, and Ciara are known for their love of cigars and their gender-flexible style.

In contemporary Western society, cigars may represent wealth and status, but all kinds of people have smoked, for all of human history. Anthropologists have found evidence of smoking as far back as 5000 BCE. A 10th century pot discovered in Guatemala depicts a Mayan smoking tobacco leaves tied together with string. Columbus picked up the habit in 1492, and brought it back to Europe with him.The cigar craze tore through Spain and France, for whose ambassador to Portugal, Jean Nicot, nicotine is named.

BBefore John F. Kennedy imposed the trade embargo with Cuba in 1962, he asked Press Secretary Pierre Salinger to secure 1,000 Cuban cigars for him. Salinger, a cigar aficionado, exceeded the request by 200. Per Salinger’s account, both Kennedy and Castro were wild for cigars; Khrushchev, who wasn’t, re-gifted Salinger 250 of them he had received from Castro. (Kennedy made a crestfallen Salinger turn them over to Customs.)

It’s not surprising that cigars have attended affairs of state. What you have to understand is that smoking isn’t just smoking. It’s ceremony and ritual. It’s slicing the cap of the cigar, the jaws of the guillotine meeting with a satisfying snap; hovering the end over an impressive flame, drawing little puffs to heat the tobacco; leaning back in one’s chair, and finally taking a real pull, saturating the palate with scents and flavors of soil, wood, fruit, acid, pepper — it’s all vague and subjective, like any sensory impression. After a few minutes, you remove the band. Then it’s smoking and drinking — a puff here, a sip there — in my case usually an overproof whiskey or scotch with just a hint of peat. The booze heightens the atmosphere and blunts the taste of the tar. As the cigar burns down, ash builds, but resist the temptation to tap it off too often; an inch of ash keeps a cigar burning longer and maintains the integrity of the tobacco. White or light gray are considered optimal ash hues. When you’re done, you’re done; experts frown upon re-lighting an extinguished cigar.

What you have to understand is that smoking isn’t just smoking. It’s ceremony and ritual. It’s slicing the cap of the cigar, the jaws of the guillotine meeting with a satisfying snap; hovering the end over an impressive flame, drawing little puffs to heat the tobacco.

Cigar-smoking affords me the pleasures of indulgence, of subversion, of procedure, all rolled into one (no pun intended). And of intimacy. Every relationship fashions its own code of symbols. In mine, cigars mean, Let’s go somewhere above the banalities of ordinary life, and mark this day as different from the one that came before it, and the one that will succeed it. The city becomes our opera; cities are operatic, full to bursting of the swings and spectacles that make up the human drama. We feel closer to one another in the mutual solitude of those evenings, the way seeing great art bonds people. Cigars are the thread that spools these nights together into one unbroken series of quiet, shared celebration.

I’I’ve smoked only a small handful of cigars in my life, maybe two or three per year for the last couple of years. My partner and I reserve them for special occasions, in part because we take the health and environmental concerns seriously, in part because a cigar is a one to two-hour commitment, and who has the time? But we’re about to move across the country, to a new and unfamiliar city, driving for two weeks in the heat of summer with a cat and a dog and a decade’s accumulation of belongings. It promises to be a bit of an ordeal, and when we arrive, listless and bleary-eyed, we’ll know hardly anyone but each other. We’ve already set aside a cigar for that first night, along with a bottle from our favorite Washington winery, a hearty merlot blend. There, on a new rooftop, overlooking a strange city, we’ll find succor on our tongues, in the rich tastes that have punctuated these last few years, which we return to again and again like a worn sweater, like a dog-eared novel, like a lover.

Gay Mag

A new magazine from Roxane Gay offering some of the most…

Jennifer R. Bernstein

Written by

writer/journalist. words in The New Republic, The Nation, LARB, Pacific Standard, Hazlitt, Gay Magazine, MEL, and elsewhere. https://www.jenniferrbernstein.com/

Gay Mag

A new magazine from Roxane Gay offering some of the most interesting and thoughtful cultural criticism to be found on the Web. Our first quarterly is coming in June 2019. We value deep explorations, timelessness, and challenging conventional thinking without being cheap and lazy.

Jennifer R. Bernstein

Written by

writer/journalist. words in The New Republic, The Nation, LARB, Pacific Standard, Hazlitt, Gay Magazine, MEL, and elsewhere. https://www.jenniferrbernstein.com/

Gay Mag

A new magazine from Roxane Gay offering some of the most interesting and thoughtful cultural criticism to be found on the Web. Our first quarterly is coming in June 2019. We value deep explorations, timelessness, and challenging conventional thinking without being cheap and lazy.

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