Most people experience heartbreak at least once. Some of us, the lucky ones, experience heartbreak multiple times, as if we are engaging in an extreme sport. But you also learn a lot about yourself in the process, and nearly always end up grateful that it happened in the first place.
When you’re in the thick of it, though, romantic movies, books, and TV shows can make you feel like throwing up. So, for this Valentine’s Day, here’s a breakdown of all the best books to read if you don’t want to even think about people happily in love—from venomous divorce memoirs to vivid explorations of enjoying the single life.
Strangers by Belle Burden
At what point, exactly, does a happy marriage turn into an ugly divorce? If we were to go through every section of a couples’ life together, when would we notice things start to curdle? This is essentially what Belle Burden attempts to tackle in her memoir of a marriage, Strangers, in which she excavates her former “picture-perfect” relationship in a bid to find answers as to why her husband wanted to leave, suddenly, after 20 years. This is a great book for anyone who’s both nosy and curious, and for anyone who may have been blindsided by a divorce or break-up themselves. Originally borne from a viral Modern Love essay in the New York Times, Strangers is beautifully written, too.
All Fours by Miranda July
If you managed to get though the first half of the 2020s without someone asking, “Have you read All Fours by Miranda July?!” then well done. If you didn’t, then… have you read All Fours by Miranda July?! And if the answer is no, then… why not?! More a story of self-discovery than a book on heartbreak, per se, All Fours is a deliciously oddball account of one woman’s attempt to lean headfirst into her sexuality—and, more broadly, what it means to be alive—during perimenopause. The actual break-up is a mere footnote in this wayward tale of exploration, motel renovations, inappropriate crushes, and really weird sex. July pushes the genre of auto-fiction to new limits here.
The Lonely City: Adventures in the Art of Being Alone by Olivia Laing
Olivia Laing has written engrossingly on everything from the whiskey-rotten livers of John Cheever and Raymond Carver to the pastel abstractions of Agnes Martin, the medlar and magnolia of her own Suffolk garden to the midcentury craze for Wilhelm Reich’s “orgone.” A 50/50 split of memoir and criticism, her 2016 work The Lonely City is a study of isolation and its attendant shame—composed after falling “headlong and too precipitously” into a relationship whose sudden dissolution left her in emotional free fall (then lurching from sublet to sublet across New York City). “There were things that burned away at me, not only as a private individual, but also as a citizen of our century, our pixelated age,” she writes. “What does it mean to be lonely? How do we live, if not intimately engaged with another human being?” While contemplating the works of Edward Hopper, David Wojnarowicz, and Henry Darger, she finds her answer.
I’m Mostly Here to Enjoy Myself: One Woman’s Pursuit of Pleasure in Paris by Glynnis MacNicol
At 46, after a year and half spent isolating in her Manhattan studio at COVID-19’s peak, Glynnis MacNicol—single, childfree, sexually charged—decamped to Paris for a month, where she devoted herself to the guiltless pursuit of sensual pleasure: through a one-night-stand with a 27-year-old met via the dating app Fruitz; by tracking down the Parisian addresses of Lee Miller and Edith Wharton; through a steady diet of rosé and chèvre; and by playing the flâneuse along the Seine and in the cool, echoing rooms of the Louvre (François Boucher’s L’Odalisque would become the memoir’s cover). That’s it—that’s the whole thrust of the book—and every page is as moreish as a cannelé.
Arrangements in Blue: Notes on Loving and Living Alone by Amy Key
Forty-something poet Amy Key had been single for 22 years when she wrote Arrangements in Blue, its structure loosely informed by the 10 tracks that make up Joni Mitchell’s 1971 album. Dedicated to “anyone who needs a love story to being alone,” the ensuing pages explore the light and shade of a life outside the “holy status” and “presumed structure” afforded by monogamous partnerships. This isn’t the book to read if you’re looking for conciliatory platitudes: “The rhetoric that you must love yourself before you can expect anyone else to love you can feel like a terrible burden,” she writes at one point. Instead, Key taps every emotional pressure point related to singledom, and ultimately offers up a sense of release. “I want to topple romantic love from its central position, hierarchy being at odds with love,” she concludes. “I can want romantic love at the same time as valuing and being fulfilled by what is present in its absence.”
Love in Exile by Shon Faye
After a “private little earthquake” of a breakup, Shon Faye, author of The Transgender Issue, doubles back on herself to pick apart her conviction that she’s “incapable of practicing the skill of love correctly.” “I consider the two belief systems that have most influenced my ideas about love, while simultaneously causing me the greatest pain,” she reflects. “First, the belief that love is instinctive, simple and transformative… and, secondly, that happiness in love is achieved within heteronormativity.” Over the course of Love in Exile’s eight expansive chapters, she tries to rewire her own mind—and considers the dueling attraction and repulsion of “traditional heterosexuality,” a detour-filled exploration that includes a paean to Lana Del Rey’s Norman Fucking Rockwell and a riposte to Germaine Greer’s The Female Eunuch, memories of queer club nights at Oxford in the aughts, and recaps of her experiences dating “alt-posh” boys with endless philosophy degrees.
Instead of a Letter by Diana Athill
Before her death at 101, Diana Athill—the formidably shrewd editor of Philip Roth, Simone de Beauvoir, V. S. Naipaul, and more—had written no fewer than nine memoirs. Released in 1962, her first, Instead of a Letter, roams from her ’30s childhood at Norfolk’s Ditchingham Hall to her career in the publishing world of Swinging Sixties London—with the aim of answering the all-consuming question: As someone who “missed the opportunity” to marry and have children, what had she lived for? Said quest forces her to reexamine a revelatory affair with an RAF pilot, and consider how their engagement’s cruel ending set her on the path to a different sort of fulfillment. “From this table, with this white tea cup, full ashtray, and small glass half full of rum beside me, I see my story, ordinary though it has all been and sad though much of it was, as a success story,” she writes near the end of the book. “I am rising 43, and I am happier in the present and more interested by the future than I have ever been.”
Further reading…
“As Orson Welles told us, if we want a happy ending, it depends on where we stop the story.” So begins Deborah Levy’s account of the years around her 50th birthday, when her marriage fell apart—and she shifted towards “a new way of living.”
Vogue’s former sex columnist delivers a forensic yet feeling study of heartbreak through the centuries that draws on the work of writers from Plato to bell hooks.
A vengeful, venomous, weirdly addictive portrait of a heterosexual marriage gone seriously wrong. This is a great book for anyone who’s ever wondered why two people who hate each other ever got married in the first place (or maybe you relate).
Jami Attenberg’s 2022 memoir, I Came All This Way to Meet You, grapples with the reality of living a peripatetic existence—sans partner and children—in order to devote yourself fully to your art. The The Middlesteins author only purchased her first real bed at the age of 45, traveling back and forth across America filling notebooks with ideas for more than three decades.
Leslie Jamison entered the running to be “the next Joan Didion” when she published her debut essay collection, The Empathy Exams, in 2014; a decade later, her account of the fracturing of her marriage after welcoming her daughter is its own lesson in sensitivity and generosity.
“Marriage is a mode of manifestation,” Rachel Cusk declares in Aftermath. “It absorbs disorder and manifests it as order. It takes different things and turns them into one thing. It receives chaos, diversity, confusion, and it turns them into form.” Her own divorce, then, represented a shattering—of a home, of an identity, of a life—a process that Cusk dissects with a surgeon’s coolness and precision.
A “thinly disguised novel” about the collapse of Nora Everything-is-Copy Ephron’s first marriage that contains both an infamous vinaigrette recipe and a landslide of aphorisms: “Let’s face it: everyone is the one person on earth you shouldn’t get involved with.”
Annie Ernaux’s masterwork of a memoir encompasses 70 years of life and a reassessment of the very nature and texture of memory… Alison Strayer’s English-language translation, published via Fitzcarraldo Editions, more than does justice to the Nobel Laureate’s taut, impressionistic prose.