One night in 1967, Maeve Brennan stood in the snow on West Forty-ninth Street and saw the past, present and future of that block spliced together: the ghost of its heyday, the garishness and shabbiness of the present, and the inevitability of some time, years off, when a photograph of the street would induce a dreamy nostalgia in some viewer who would have, in their own version of the city, a new kind of shabbiness or garishness to abhor. “It will have,” Brennan wrote, “to be a very old photograph, deepened by time and by a regret that will have its source in the loss of all of New York as we know it now. Many trial cities, facsimiles of cities, will have been raised and torn down on Manhattan island before anybody begins to regret this version of West Forty-ninth Street, and perhaps the photograph will never be taken.”

Nostalgia, for Maeve Brennan, was like the genetic inheritance of becoming a New Yorker; you felt it for the city you had known, for the city you had arrived too late to know, and even for the city as it would be without you. Her long-winded lady columns, which appeared in The New Yorker between 1954 and 1981 (the piece quoted above, “A Snowy Night on West Forty-ninth Street”, was in fact published first as a feature and later as a short story, but it is very recognisably of the long-winded family), are a remarkable archive of a city not just as it was during two decades of its life—the fifties and sixties, when most of Brennan’s “communications”, as the magazine framed them, appeared—but as it was to some of the people who inhabited its apartments and its hotels and its boarding houses during that time, as it was towards them, and towards one of them in particular. Pulsing out of the images and the observations, the caught conversations and the apparently stray thoughts recorded and recreated in these pages are the realities of what it was like to be three things in mid-twentieth century New York: female, alone, and an outsider. Like the past, present and future of Brennan’s Forty-ninth street vision, these three experiences, in a fundamental way, went together in this city, and part of what makes Brennan’s columns so valuable is the way they render any nostalgia for that time a very complicated business.

Cocktails in those little West Village restaurants; the new fashions in Saks; breakfast in the Plaza; the hallowed corridors of The New Yorker, when William Shawn and William Maxwell and Jean Stafford were on the job; the new skyscrapers, silver glints of promise climbing high: the idea of mid-century Manhattan has long operated as a shorthand for glamour. The most famous fictions of that era did little to dismantle this notion, even as they explored lives which were privately miserable or grasping; the stories of John Cheever and Richard Yates may be about men in crisis, but they are always having a damn good time in the city while they’re at it. The girls-about-town, the dimly-lit bars on Third Avenue, the dusky light tumbling in through the long windows of Grand Central.

Meanwhile, in The New Yorker, a writer identified only by a vaguely insulting sobriquet was telling the story from the perspective of the girl-about-town—who was not a girl but a woman—and it was devastating. It was not miserable, not self-pitying; it was, in fact, the very opposite of these things. That was how it worked its unnerving magic. It was the story of such ordinary places, such slow-news-day settings that it must have been almost a shock to see them occupy the mahogany-and-brass booths of “The Talk of the Town”, the magazine’s famous front section. Yes, that section had always been a home for vignettes about city life, but not for vignettes from a supermarket, for goodness’ sake, or from the aisles of a shoe store, or from the standing-rail of a subway car, or from tables-for-one in empty restaurants, or from the couch of small rented apartments shared with cats, and the sight of pigeons, and the sound of rain. So often, the sound of rain.

Maeve Brennan’s act of rebellion, as the long-winded lady, was to write New York as the city of a woman with ordinary things to do in the morning and with a love, in the mid-afternoon, of sitting by herself in little restaurants, staring at people, eavesdropping on their conversations while pretending to be absorbed in a book. She made no apologies for her nosiness, and she made no apologies for the defiantly quotidian detail of her errands, of her routes on foot, of the random thoughts and wonderings and memories which popped into her head and back out again. “Well, there you are, in case you’ve paid any attention,” the first column ended, in 1954. “It was the moment of no comment,” ended a 1962 piece, about the experience of observing two passing nuns from a restaurant window, and then, in case the strangely unyielding conclusion had not baffled readers sufficiently the first time around, “It was the moment of no comment,” again. On a page of The New Yorker which had always been about charm—a charm possible because it came from a place of easy privilege—Brennan created a persona who was still charming, but also a challenge. She took the reader deep into her experience of their shared city, with a specificity of location and neighbourhood which, sixty years later, still makes a New York reader feel as though they are walking with her through these very streets, past these very buildings, into this very zone with its stubborn personality—but she also makes the reader feel, frequently, as though they have slid into the opposite chair at her one-top and are being stared at in a way that says, Go home.

Until they were first collected for publication in 1969, the long-winded lady columns were unsigned, as was the tradition with “Talk” pieces. Brennan was in a good spot with The New Yorker when she started out as the lady; she had published seven short stories with the magazine in two years, with another one on the way, and she was also writing book reviews. She had an office, she had colleagues, she had readers. She had her city; by 1954, it had been her home for twelve years. Brennan had been born in Dublin, but had spent her late teens and early twenties in Washington, DC, where her family had moved due to her father’s job as the first Irish envoy to America. Taking herself to New York, she worked first at the Public Library and then at Harper’s Bazaar, writing fashion copy for the Irish editor Carmel Snow. While still there, she published some short pieces in The New Yorker, and Shawn invited her to join the staff in 1949.

The long-winded lady does not have an Irish accent. Not a trace of one. Only once in the 1950s and 1960s columns—in “Lessons and Lessons and Then More Lessons”, that piece about seeing the nuns—does she mention her upbringing in Dublin, and that this detail also reveals her Catholicism is actually quite startling to think about, because if anything characterised the lady, it was her refusal to share any personal background which might place her, even momentarily, at a distance from her identity as a New Yorker, as a Manhattanite through and through. The nuns rattled her, but nothing like this happened again. Her voice, her cadence, her colloquialisms, make it seem as though she were not just from the city, but of it, born of its rhythms and its oddnesses, rather than of any inconvenient humans who might have tripped along its way. The city, she wrote in 1968, “has a real horizon made of buildings but it also has an eternal horizon… created when water and air work together.” It was important to her to seem as though she had strolled out of that horizon, watchful from the very first moment, and that when the time came, she would simply slip into that horizon again.

But a horizon cannot be a home. Where the long-winded columns become devastating is in the search for home that they enact almost in spite of themselves. Before she joined The New Yorker, Brennan completed the manuscript of her novella, The Visitor, about a young girl, Anastasia, who is sent to live with her grandmother, but sent away again. Anastasia’s anguish fixes with painful clarity on the question of how to belong: “Home is a place in the mind,” the narrator tells us after the child’s awkward arrival on the doorstep. “When it is empty, it frets. It is fretful with memory, faces and places and times gone by. Beloved faces rise up in disobedience and make a mirror for emptiness.” When the lady allows herself to countenance the idea of homesickness, she keeps to a similarly—although more urbane—poetic register, which offers the safety of abstraction even if it is talking about the travails of living in a very particular place: “New York does nothing for those of us who are inclined to love her except implant in our hearts a homesickness that baffles us until we go away from her, and then we realise why we are restless. At home or away, we are homesick for New York not because New York used to be better and not because she used to be worse but because the city holds us and we don’t know why.”

Actually, the city seemed hard for Brennan to love, partly because it kept changing, kept dismantling itself and remodelling itself around her, indifferent to her needs, emotional or otherwise. It’s what the city has always done; the cri de coeur against demolition, development, the disappearance of beautiful old buildings and the mushrooming of ugly new ones which sounds in the long-winded columns from as early as 1955, and right up to the 1970s, could be sounded by any writer living there today, and it will be the same, no doubt, for a writer living in the city in 2060, looking at an old photograph. But for the lady, the fact of this change seems truly impossible to accept, to live with; again and again, she stands in a street and watches what the wrecking ball has done, or is doing, to her city: exposing the painted rooms of the broken buildings, spilling all their secrets, crumbling them away. It becomes a repetitive presence in her narrative. “Nobody will care when this street comes down,” she writes in 1967, “because nobody really lives here.”

And yet Maeve Brennan lived there, in one of a series of hotel rooms she rented over the years. The columns are careful to present melancholy as an aesthetic position, as a kind of sweet nostalgia in itself. Brennan herself decided their order in the 1969 collection; they were not presented chronologically, but in a thematic or atmospheric curation which resists easy interpretation. But the columns’ sharpest power arguably lies in the way their actual chronology—they did not appear regularly, sometimes not for years at a stretch—traces their author’s difficult reality. In the things the lady notices about her fellow citizens, in the things she notices about her city, in the way she moves through it, we learn a lot about how hard it was, in this city, for a woman who liked being alone, who wanted to be alone—who enjoyed her own company and knew how to write brilliantly out of that company—to feel at home. In “The Traveller” (1963), she wishes, sitting in a public place, that she had a suitcase. A suitcase, she writes, “would translate me to everybody’s satisfaction and especially to my own satisfaction.”

Translation is in itself a form of demolition, or perhaps of remodelling; what the lady reveals in this moment is the pressure she must have felt, so often, to appear as someone other than herself, as other than the wilfully solitary, beadily watchful, book-loving, martini-drinking, single woman (and, eventually divorcee) that she was. In the later columns especially, her anxiety about what will become of her, and about how she will be treated by the city on which she is dependent, leeches into her portraits of those around her. There are so many shaky or shattered older women in these columns where previously there had been eccentric and intriguing characters of both genders; now it is the shadows she fears becoming who seem to catch her eye. The saddest thing, of course, is that she did end up desperately vulnerable on the streets of her city. By the 1970s, even as she wrote the last of the columns in these pages, she was suffering the ravages of a mental breakdown which saw her become paranoid and lost, even homeless for a time.

But here is her younger self, playing Patience impatiently. Here she is stalking Julie Andrews in the Algonquin. Here she is encountering a tiny and terribly behaved dog, and his Vladimir-and-Estragon-like owners, at a downtown vet’s. Here she is enjoying the sight of an arrogant man falling out of his restaurant chair in Longchamps, one of her beloved often-empty places. Here she is watching a busload of tourists, all women, give hell to their unfortunate driver on Sixth Avenue. Here she is hate-reading a profile of the new female president of Henri Bendel in Life magazine. Here she is observing a Vietnam War protest. Here she is getting new shoes. Here she is listening to the merciless gossip of two women about a third. Here she is writing out the words of Ludvík Vaculík’s manifesto when the Prague Spring was new. Here she is sipping her drink—there was always a drink, which is also part of the unspoken story—and letting her gaze fasten onto her next story. Here she is shopping for a plain glass orange squeezer and, accidentally, in the same store, spotting a charm of finches in a cage.

Here she is.