WHAT CAN WRITERS DO with the subject of loneliness? Distilled, loneliness lacks the elements of a good story. It may be the product of drama — abandonment by a lover, loss of a friend, uprooting and relocation — but the feeling itself is nonnarrative and sedentary. When it comes to tone, loneliness is quicksand: attempt to represent its bleakness, and risk sounding like a Raymond Carver wannabe; describe its watery wellings-up, and be dismissed as a self-indulgent sap. It presents, on top of everything, a problem of knowledge: everyone feels it, but no one can share in it. Two lonely people in the same room are not together, and if one could grasp the full shape of the other’s loneliness, then would they really be lonely anymore? Writers must desire to connect to an audience, but, in loneliness, we are all solipsists.

This is a problem I’ve considered as a writer who currently happens to be lonely. Lonely by choice, even; lonely from a conviction that something of importance lurks inside loneliness. Last fall, I turned my longest-running partnership into a long-distance one, moving from Washington, DC to Boston — for professional reasons, but also as an excuse to take up residence in my own gabled apartment. I am in the stage in which record numbers of Americans live alone, post-college and pre-probable-marriage. I felt compelled to embrace solitude while I still had time to prove that I could, and, at its pith I expected to find a beneficial struggle. I had a jingoistic faith about “what doesn’t kill you,” a belief that what is hard must be worthwhile.

Perhaps it will be. But I found myself resisting the idea of writing about loneliness by writing about my own loneliness. My attempts to peel the exoskeleton off of the feeling and subject it to the heat of the personal essay’s inward gaze only ever produced useless piles of jelly.

I was scrolling through lists of forthcoming books late at night (hard to enforce rules like “no screens in the bed” when a computer provides such varied company) when I first saw Olivia Laing’s The Lonely City: Adventures in the Art of Being Alone, a memoir-cum-cultural history that explores loneliness — in particular, the modern, urban variety — from without as well as within. Like me, Laing grew interested in loneliness when she found herself adrift in it. She fell in love and left her native England precipitously for New York, only to be stranded when “the false spring of desire,” as she calls it, turned cold. As a writer, she wants neither to pathologize loneliness, as so many popular science pieces do, nor to romanticize it. Instead, she posits, “Perhaps I’m wrong, but I don’t think any experience so much a part of our common shared lives can be entirely devoid of meaning, without a richness and a value of some kind.”

Most intriguingly to me, Laing has found a canny, outward-facing architecture to hold up the viscous topic of loneliness. She borrows from the structure of her last book, The Trip to Echo Spring: On Writers and Drinking, which chronicles the alcoholism of six famous authors. In loneliness, however, Laing felt herself “beginning to fall in love with images, to find a solace in them that I didn’t find elsewhere.” She chooses as her pillars four 20th-century visual artists whose work seemed to her “to articulate or be troubled by loneliness”: Edward Hopper, Andy Warhol, David Wojnarowicz, and Henry Darger.

“Loneliness, I began to realise, was a populated place: a city in itself,” Laing writes in her opening chapter, which presents the book as an idiosyncratic and personal “mental map” of this shared land. The form of her project, and the way she suffuses it with empathy for her subjects, resists the solipsism of loneliness. But the effort to be universal brings its own problems; in moments, Laing’s act of cartography threatens to flatten the complex territory of this particular sadness. When it comes to a feeling so individual, so incommunicable, how can a writer faithfully reflect it — how can she avoid simply etching the lessons of her own experience over the unfamiliar emotional topography of the loneliness of others?

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Laing understands the problem that the solipsism of loneliness poses for her book. She expresses interest in “the idea that loneliness might be taking you towards an otherwise unreachable experience of reality.” And she overcomes this epistemological roadblock by finding an illustration of isolation itself — and one that virtually every one of her readers will have seen: Edward Hopper’s Nighthawks. Scrutinizing the painting in a museum, Laing is struck by the fact that the famous diner is “a glass cell,” with no door to the street, and that the server seems trapped within the enclosure of the counters. “This is the kind of subtle geometric disturbance that Hopper was so skilled at,” she notes. Loneliness is the simultaneous experience of being trapped inside the diner and of watching from outside on the desolate streets. She even assigns urban loneliness a color: the “noxious pallid green, which only came into being with the advent of electricity, and which is inextricably associated with the nocturnal city, the city of glass towers, of empty illuminated offices and neon signs.” In her close reading of Hopper, Laing gives the translucent pain of loneliness visible features, ones anyone who goes on Google Images can see.

In Warhol, Laing finds a perfect avatar for modern loneliness. The impresario of The Factory is in some ways her most surprising choice of subject, but she argues convincingly that he orchestrated his busy world from behind a barricade of cameras and tape recorders — machines that were always running, and which positioned him as an observer even as he sat at the center of his circle. “The acquisition of my tape recorder really finished whatever emotional life I might have had, but I was glad to see it go,” he once wrote. It’s impossible to discuss contemporary loneliness without acknowledging the role of the internet, and Laing in some sense echoes Warhol, later in the book, in her diaphanous descriptions of online life:

Whole days went by on clicking, my attention snared over and over by pockets and ladders of information; an absent, ardent witness to the world, the Lady of Shallot with her back to the window, watching the shadows of the real appear in the lent blue glass of her magic mirror.

Laing’s aim here is not simply to describe loneliness, however, but also to find that “richness,” that “value of some kind.” And the version she hones in on comes through most clearly in her portrait of David Wojnarowicz, the experimental artist-turned-prominent AIDS activist, who, as Laura Miller wrote in her excellent review for Slate, “floats above The Lonely City like a lanky, downtown version of the saints in Renaissance church paintings.” Wojnarowicz had experienced the ravages of loneliness: he was raised by an unstable, alcoholic father who beat him with dog leashes and once cooked his pet rabbit and served it for dinner. Realizing he was gay nearly drove him to kill himself; instead, he spent his teenage years homeless and turning tricks in Times Square. As an adult, he remained, in the words of one boyfriend, “essentially […] a loner.” And yet, as Laing marvels, so much of his art and writing celebrated the blooming underground world of New York’s gay community, and celebrated the joys of sex, which, no matter how casual, “David almost always both named and viewed as love-making.” Laing dwells in particular on Wojnarowicz’s series of “Rimbaud” photographs, in which the artist photographed his friends wearing a mask of the French poet’s face, surveying the haunts of his tormented childhood. With these photos, Laing muses, the artist sent a desperately needed friend — a protector, a familiar of some kind — tunneling through time to his younger self.

Of course, Laing is not the first to meditate on Wojnarowicz’s interest in loneliness; the photographer has pondered it himself. Wojnarowicz described the goal of his memoir, Close to the Knives, to an interviewer in 1990:

I want to make somebody feel less alienated — that’s the most meaningful thing to me. […] I think part of what informs this book is the pain of having grown up for years and years believing I was from another planet. […] We can all affect each other, by being open enough to make each other feel less alienated.

Only a person like Wojnarowicz — or Laing herself — who has experienced the pain of separation from the world behind the glass walls of loneliness could be so urgently motivated to melt the barrier down, to reach a hand through.

Laing’s investigation of loneliness is profoundly complicated by her inclusion of Henry Darger, a man who did not, as Warhol professed to, choose his stance akimbo to the world, or, like Wojnarowicz, manage to reimmerse himself in a beloved community. Can she still find “value” in loneliness as exhibited by Darger, a recluse and a hoarder who, biographers have postulated, likely suffered from schizophrenia? Orphaned as a child, he grew up in the Dickensian bleakness of a series of boys’ homes and spent his adult life working as a janitor, dishwasher, and bandage-roller at hospitals in Chicago. It was only when he was forced to move into a nursing home at the age of 72 that his landlord discovered in his room a 15,000-page manuscript; it chronicled a war between a cadre of supernatural female children — the “Vivian Girls” — and the forces of evil in the “realms of the unreal” that Darger seems to have inhabited in his mind. Its dramas came to life in a cache of disturbing and magical art; The New York Times has described Darger’s oeuvre as:

huge, fantastical landscapes with baby-faced girls, some clothed in colorful dresses, bathing suits and pinafores, and others naked […] girls with horns and others with penises […] some being disemboweled or strangled, tongues lolling out […] others enjoying the sunshine, the butterflies and the huge flowers.

Laing’s writing about Darger flexes the kind of radical empathy that she admires in Wojnarowicz. The canonical interpretation of Darger assigns him little agency: either he was compulsively expressing his twisted sexual fetishes, or he was compulsively recalling his own childhood abuse. But Laing proposes that Darger may also have been “carrying out a conscious and courageous investigation into violence: what it looks like; who its victims and perpetrators are.” She writes, “It’s not only factually incorrect to assume mental illness can entirely explain Darger; it’s also morally wrong, an act of cruelty as well as misreading.” She retrieves Darger from his classification as “other,” recasting him as a victim of that suffering we can all recognize: loneliness. And though my notes in the margins included a few variations on the thought, “I wonder if loneliness is a strong enough word for this?” I was ready to go along with Laing — especially when she used Darger to introduce a new thesis: in loneliness, the personal is political. We shouldn’t condemn or pity Darger without also acknowledging “the role that structures like families and schools and governments play in any single person’s experience of isolation.”

Here, Laing seems to have hit upon the perfect concept to further her investigation of loneliness: the feeling itself may create an “unreachable experience of reality,” but it doesn’t take place in a vacuum. Perhaps by comprehending the social forces that contribute to loneliness, we can close in upon the thing itself — can capture its image by way of negative space.

Unfortunately, the desire to do justice to this idea seems to induce Laing to zoom out rather than in — to abandon the sure-footed meanderings of her four artists’ portraits for textureless sweeps of historical summary. The dim point in the otherwise lucid Darger chapter occurs when Laing brings in psychological experiments — specifically, Harry Harlow’s infamous mid-20th-century rhesus monkey trials, in which animals raised in solitary confinement emerged emotionally disturbed and were ostracized by their fellows — in an attempt to explain why Darger, after his troubled childhood, rejected the world as much as it rejected him. Instead of fleshing Darger out, the application of this scientific lens seemed to inadvertently flatten him; to seek understanding through a formula instead of Laing’s own methodically unfurled compassion.

Similarly, in a chapter about the AIDS crisis that ravaged Wojnarowicz’s community and, ultimately, took his life, Laing adopts the language of activism to write about activists, and the jingoism of politics to talk about the politics of loneliness. As Miller wrote at Slate, “the language she summons to respond to this — words like ‘resistance,’ ‘solidarity,’ ‘the system of America itself’ — have the threadbare lifelessness of slogans. […] [T]here’s a weird irony to a celebration of idiosyncrasy and freakishness that seeks comfort in pro forma exhortations.”

Laing switches into the voice of the paranoid polemicist in her writing about the art of the internet age, which centers on Josh Harris’s “Quiet: We Live in Public,” a real world-type experiment in which volunteers lived in a house under constant surveillance. She writes dramatically:

I think we’re all in Josh’s room now. I think the salient point about the new world we’ve been drifting into is that all the walls are falling down, everything blurring into everyone else. In this atmosphere of perpetual contact, perpetual surveillance, intimacy falters. […] Meanwhile, the life forms on the planet that we inhabit diminish by the hour. Meanwhile, everything becomes steadily more homogenised, more intolerant of difference. Meanwhile, teenagers kill themselves, leaving suicide notes on Tumblr, against a backdrop of flinching, flickering Hello Kittys […]

So much for the value of loneliness. Is the focus of the book spinning outward — or is Laing tumbling inward, into the highly subjective fears that can loom large in the minds of the isolated? Either way, the subtle interweaving of inward and outward, personal and universal — a balance between centrifugal and centripetal forces that had kept the book centered — has, by this point, blown entirely apart.

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When I was working on this piece, I heard the poet José Olivarez read his beautiful poem “Ode to the First White Girl I Ever Loved,” in which he describes the loneliness of growing up in the United States as the son of Mexican immigrants:

Everyone was rich and white.
My family was poor and Mexican.
My family only spoke Spanish

And in school I felt so lonely.
My loneliness would walk home with me.
My loneliness held my hand as I crossed streets.
My loneliness spoke Spanish like my family.

And this is how I learned to equate
my family with loneliness,
how I learned to hate my family,
how I learned to hate being Mexican.

Whenever I sat down to think about loneliness, this image would return to me: two children, one real, the other a shadow. It expressed what I had been feeling: that one’s loneliness is in a sense a version of oneself, without the moderating influences of companionship and contentment. Maybe the form it takes is not even human. In another poem that runs through my head often, Maxine Kumin’s “After Love,” the poet describes loneliness as “the wolf, the mongering wolf / who stands outside the self.” Every person’s loneliness is distinct, and every person’s relationship to that loneliness is, in some way, her relationship to herself.

My own loneliness, as I’ve said, was self-inflicted. I found myself in my mid-20s, still happy in a relationship that I’d entered into at the lintel of my adulthood, and I started to fear that I didn’t know how to be alone. I didn’t want to break up with my partner — so instead, I moved hundreds of miles away from him, into my own apartment, in the hopes that if I could experience perfect dominion over my space, I would finally be confident in my dominion over myself. I had read Virginia Woolf’s A Room of One’s Own; I had read interviews with Cosmopolitan founder Helen Gurley Brown, who in her 1962 book, Sex and the Single Girl, advised women that, for at least a few years before marriage, “you need an apartment alone even if it’s over a garage.” When I thought about a future that might include marriage, family, I felt an urgent need to shore up the boundaries of myself. Loneliness seemed like the only way.

For a long time, I wondered if I’d made a mistake. In the mornings, I was happy: I brewed my black tea with a splash of milk and carried a steaming mug across the hall into my office, where my desk sat snugly underneath a steeply slanting eave. For hours, I could be content. The problem was the way the shadows lengthened in the afternoon. It was the act of turning on the lamps — the round one in the office; the square one in the kitchen; the overhead in the hall; and finally, the green ceramic on the bedside table — that made me feel embattled. I summoned fields of glow to fend off the seep of cool, grim silence. But if the feeling set in too deeply, I could leave the apartment, could go out and drink wine in front of a fireplace and eat chicken piccata that a friend had prepared for me, and still not be able to rid myself of the chill. The empty apartment was there inside of me all night, and I stretched out the goodbyes forever, bracing myself against the need to go back.

I didn’t feel that my loneliness had “richness.” I was holding onto it for reasons that were symbolic and political: in practice, I felt that my relationship fit me, but in theory, I’d surrendered my independence far earlier than I’d ever planned. I wondered how that looked to other people. And I wondered if it exposed a lie at the center of my idea of myself. When I read Rebecca Traister’s book about the radical social transformations wrought by single women, All the Single Ladies, I lingered over the sentences: “When I married my husband in 2010, I was thirty-five and he was forty-five; we have lived a combined eighty years without each other […] What was undeniably true was that one of us was not simply going to subsume the other.” Traister writes about having lived “14 independent, early-adult years that my mother had spent married.” In relation to my own parents, who met in their 30s, I felt myself to be headed the wrong way. Some part of me clutched instinctively at the idea of killing time, of waiting out the years until the gap between my life and my desired identity had closed.

Of course our loneliness is inflected by who we are; by how we came to feel isolated; by how we want our solitude to be perceived by the world. Laing has beautifully repurposed the idea that “the personal is political,” one of feminism’s best slogans, to express this — and yet, she doesn’t seem to want to dwell on it. Of the despair that followed her breakup, she notes, “I don’t suppose it was unrelated, either, to the fact that I was keeling towards the midpoint of my thirties, an age at which female aloneness is no longer socially sanctioned and carries with it a persistent whiff of strangeness, deviance and failure.” In a later passage, in which Laing remembers growing up with a lesbian mother, she writes,

I’d never been comfortable with the demands of femininity, had always felt more like a boy, a gay boy, that I inhabited a gender position somewhere between the binaries of male and female, some impossible other, some impossible both. Trans, I was starting to realise, which isn’t to say I was transitioning from one thing to another, but rather that I inhabited a space in the centre, which didn’t exist, except there I was.

This is a tantalizing revelation, but it’s all we get.

Doesn’t an investigation of the politics of loneliness necessitate consideration of the politics of identity? This is where Laing falls frustratingly short. Perhaps she could have tunneled deeper into herself, into the entanglement of her gender and her loneliness. She would not have needed to use her own story as an entry point; as a scholar and critic, she could have found any number. The book’s efforts to capture how loneliness flows through the sluices of social power and powerlessness are handicapped by her choice of subjects: although the book is interwoven with smaller portraits of women artists and artists of color — among them Valerie Solanas, Nan Goldin, Jean-Michel Basquiat, and Billie Holiday — the fact remains that Laing takes us farthest into the minds of four white men.

Perhaps Laing is shying away from seeking “richness” in loneliness that comes braided together with the violence and oppression of sexism and racism. It’s an uncomfortable project, certainly — but not an impossible one. Consider Maggie Nelson’s Bluets, a gorgeous meditation on a specifically female imprisonment inside a blue mood. Struggling to come to terms with a lover’s betrayal, Nelson crafts a circular ars poetica — a book about a woman trying and failing to write a book, which both is and is not this book, about the color blue; the Russian doll structure mirrors the lonely person’s retreat from the world. Nelson satirizes her sadness — in one passage, she writes about picking up a book called The Deepest Blue: How Women Face and Overcome Depression in a store, saying, “I quickly return it to its shelf. Eight months later, I order the book online” — but she also represents it as lushly, even erotically beautiful. She describes her monomania for blue as both blessing and curse, as “a spell I fought to stay under and get out from under, in turns.”

Or consider Roxane Gay, who has written that, as a black woman writer and academic, and a person who has at points identified as queer, “I am still writing my way toward a place where I fit.” In an essay called “Feel Me. See Me. Hear Me. Reach Me,” Gay makes it clear that no amount of success in her field will ever shield her from being treated as an outsider. But she also suggests that this pain is partly responsible for her writerly voice’s blunt warmth, and for the apostatic confidence with which she has famously declared herself a “bad feminist.” “Writing bridges many differences,” Gay says, vowing: “I will keep writing about these intersections as a writer and a teacher, as a black woman, as a bad feminist, until I no longer feel like what I want is impossible.”

When Laing writes about sufferers of a distinctly political loneliness, her observations become uncharacteristically two-dimensional. Her brief portrait of Billie Holiday, for example, reads largely as a list of hardships that the singer endured:

Billie Holiday, who gave voice to loneliness both personal and institutional, who lived and died inside it, a life short on love and brutalised by racism. Billie Holiday, who was called Blackie to her face and made to take the back door even in venues where she was herself the headline act, wounds that she attempted to medicate with the poisonous ameliorators of alcohol and heroin. Billie Holiday, who in the summer of 1959 collapsed in her room on West 87th Street while eating custard and oatmeal, and who was taken first to the Knickerbocker and then to the Metropolitan Hospital in Harlem, where she was left — as so many AIDS patients would be in the years that followed, particularly if they too had black or brown skin — on a gurney in a corridor, just another dope case.

Laing also incorrectly identifies Holiday as the author of “Strange Fruit” (for that, we can thank a Jew from the Bronx named Abel Meeropol, though Holiday, of course, turned words on a page into one of the most important pieces of music in American history). Laing, who worked so hard to dignify the tragedy of Darger’s life, does not honor Holiday with the same level of agency. And yet Holiday, in her autobiography, Lady Sings the Blues, reveled in being inscrutable, even unreachable: the fact that even her critics couldn’t “put any label on me” was, to her, “the biggest compliment they could pay me.” The flipside of her loneliness was the independence that made her an artist.

Reading Laing on Holiday, I was reminded of Elizabeth Hardwick’s portrait of the singer in her autobiographical novel, Sleepless Nights. As Darryl Pinckney has written of Hardwick at The New York Review of Books, “she wanted to evoke a singularly conscious individual, someone who had worked to perfect her art, a singer who knew what she was doing, a supreme musician.” Sleepless Nights is, for me personally, the best realization I’ve read of the idea that loneliness is intertwined with the politics of identity. This is Hardwick after the death of Robert Lowell, observing the world from inside the numb watchfulness of what she terms a “sedentary sleeplessness,” her gimlet eye drawn to loners who range from homeless women to Brahmin widows. She is especially good at capturing the different sheens that gender puts on solitude: a male friend clings to his aesthetic of bachelordom while living off an heiress; meanwhile, newly divorced women corner Hardwick at a party to ask, with almost unbearable earnestness, if she’s lonely (when she says, “Not always,” they answer, “Terrific”). But Sleepless Nights’s most memorable passage may be its description of Holiday’s radical self-possession:

The sheer enormity of her vices. The outrageousness of them. For the grand destruction one must be worthy. […] With cold anger she spoke of various cures that had been forced upon her and she would say, bearing down heavily, as sure of her rights as if she had been robbed: And I paid for it myself.

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Laing closes her book with a meditation on Zoe Leonard’s “Strange Fruit (for David),” which borrowed the name of Holiday’s song and its evocation of lynching to protest the government’s apathy toward AIDS. “Strange Fruit” was also a tribute to Wojnarowicz, for whom Leonard grieved by using a needle and thread — along with “zippers, buttons, sinew, stickers, plastic, wire and fabric” — to stitch together 302 empty orange, grapefruit, lemon, and banana peels, and the alligator-textured skins of avocados. Around this image, Laing weaves an entire chapter about “[a]rt that repairs, art that longs for connection, or that finds a way to make it possible” — from a photo of Warhol in one of the corsets that held his body together after Valerie Solanas almost killed him, to the revelation that Darger collected bits of string on the street and tied them together in his tiny room.

This is the beautiful “value” that Laing finds in loneliness: it teaches us to live, and make art, in what she terms the “fragile space between separation and connection.” Loneliness lends urgency to the effort to reach beyond ourselves, but it also shows us how little about other people we can ever truly understand. From Gay’s “writing my way toward a place where I fit” to Leonard’s sutured avocado skins, loneliness teaches us to be endlessly inventive in our means of connection.

Though Laing never manages to fully make use of her insight that loneliness is both personal and political, her conclusions provide a powerful model for how to live within a diverse and complex society. They remind us that each person’s reality is essentially “unreachable,” and that our only strategies for seeking understanding are the same ones that Laing used to map the unknowable territory of loneliness: we can arrange what we know from looking at our own experience alongside what we can discern about the experiences of others. We can use empathy to stitch up what we’ve pieced together. We can remain humble in the face of the gaps.

The Lonely City is proof that Laing found considerable value in her loneliness. Since reading it, I have also begun to find value in mine. As befits a mongering wolf, it gives chase when I try to run; the more I fill my weeks with wine bars and dinner parties, the closer I find loneliness when a night is empty or a plan falls through. But the more I stay home — like Laing on her laptop, reading about the world outside from within the protection of my solitude — the more I find that my loneliness is tame. On these nights, it curls up like a cat on the opposite chair, nose under tail, content to keep me company from just out of reach.

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Nora Caplan-Bricker’s work has appeared in Slate, NewYorker.com, The New Republic, Pacific Standard, and elsewhere.