Sometimes the best way to deal with a broken heart is to break it even deeper.

Confession: Despite writing a somewhat “uplifting” and quirky book on heartbreak, my personal reading need after a breakup is actually to be further devastated. Science backs this up with studies on how sad movies make you happier. For more right-brained “logic,” the poet Mary Ruefle offers in her anti-lecture this beautifully true line: When a little girl is sad, a doll with a sad face makes her happy. So here are 16 books for those times when the best way to deal with your broken heart is to break it even deeper.

Read any fairy tale and you’ll find that hidden in childhood is a dark heartbreak. This stunning collection captures the particular brutality of girlhood and growing up. “Note to Sixth-Grade Self” is a short story told in second-person from the perspective of an adult both looking back at and talking to her younger self. She returns to the year she dared to disrupt the status quo by dancing with middle-school heartthrob Eric Cassio, eliciting the ire of the unredeemable Mean Girls (one has a “fascinating stutter”). This is the story for anyone who has fallen in love with the possibility of a person, instead of who he or she really is. It’s for anyone who hoped against hope that the object of your heart’s affection could live up to the image you desperately held on to, when deep down you already knew he could not come through. It’s the one story I return to again and again when I am most in need of emotional obliteration.

Get it from Amazon for $13.38+, Barnes and Noble for $14.40+, or find it at IndieBound or your local library.

2. When your BFF breaks your heart: Marlena by Julie Buntin Henry Holt, juliebuntin.com

In the vein of Lorrie Moore’s Who Will Run the Frog Hospital?, Marlena expertly captures that time in your teenage life when your fascination with your cooler best friend is way more compelling than any romantic crush. Catherine, now in her thirties, is still haunted by her past and the ghost of her former best friend, Marlena, who was amazing and dangerous and everything shy and bookish Cat believed she could never be. This debut burns with a blend of coming-of-age novel and literary thriller, and beautifully renders how hard it is to both live through and then come to terms with your first complicated female friendship. Buntin sears the reader with her vivid depictions of adolescence, loss, and longing.

Get it from Amazon for $5.95+, Barnes and Noble for $14.40+, or find it at IndieBound or your local library.

When My Brother Was an Aztec by Natalie Diaz 3. When your family breaks your heart:by Natalie Diaz Copper Canyon Press, Rachel Eliza Griffiths

Natalie Diaz grew up in the Fort Mojave Indian Reservation Village and writes with unflinching compassion about family, poverty, and addiction. Her portrayal of reservation life brings a fresh and necessary perspective to the poetry landscape, but it’s her deeply affecting poems about her brother, who struggled with meth addiction, that will resonate with anyone who has experienced the excruciating pain of not being able to reach or recognize the person you love. She confronts her own empathy as she also inhabits her parents’ suffering: “he lived in our basement and sacrificed my parents / every morning. It was awful. Unforgivable. But they kept coming / back for more. They loved him, was all they could say.” This is the double heartbreak of losing the person you love twice — emotionally first, and then physically. Get it from Amazon for $13.32, Barnes and Noble for $15.41, or find it at IndieBound or your local library.

There should be a name for that specific reader’s heartbreak, the sadness you feel when you finish a book you don’t want to end. Whatever the neologism turns out to be, a John Green novel has got it in spades. The last pages of this book are so epic in their bittersweetness that I literally made a friend read it immediately after I finished, so I could have some kind of emotional support group to get me through its unexpectedness. What starts out as a YA mystery quickly develops into a deeply personal exploration of mental illness and first love. While it can be argued that the main love story belongs to the protagonist Aza and her best friend Daisy, it’s Aza’s reconnection with her boyfriend Davis, who also lost a parent, that propels the story forward. Despite the couple’s chemistry and deep connection, our heroine’s extreme anxiety and obsessive-compulsive disorder prevent her from moving forward too. Turtles All the Way Down is a painfully beautiful metaphor for anyone afraid to let down their walls and risk the messiness of love.

Get it from Amazon for $14.58+, Barnes and Noble for $15.29+, or find it at IndieBound or your local library.

5. When you're heartbroken, but still feisty: Virgin by Analicia Sotelo Milkweed, analiciasotelo.com

The speaker of Sotelo’s Virgin redefines vulnerability in a collection of poems that combine unrequited feelings, myth, fatherlessness, and heartbreak with a sense of humor, sensitivity, and feistiness. The titles alone will tell you that these are not your grandma’s love poems: “I’m Trying to Write a Poem About A Virgin and It’s Awful,” “Trauma With White Agnostic Male”. Sotelo nails the single girl perspective, skewering incredibly unfun scenarios like attending a backyard barbecue, where your unrequited love is in charge of the grilling and everyone but you is enjoying the guacamole and seemingly in love. Sotelo’s virgins rage with heartbreak and humor (“All my acquaintances are coupled up / like hamsters with advanced degrees”). They are unafraid to dive deep into their bruises and the humiliation that sometimes, unfairly, comes with solo status: “The virgins are here to tell you to fuck off … The virgins are certain there’s a circle of hell / dedicated to that fear you’ll never find anyone else.”

Get it from Amazon for $14.71, Barnes and Noble for $15.15, or find it at IndieBound or your local library.

In her signature unflinching style, Gay unpacks the particular heartbreak of living in an obese body in a world that discriminates against fatness and marginalizes fat people. Gay writes candidly about being gang-raped as a young girl and links it to her need to protect herself from her excruciating past and the threat of future harm by making herself physically big. This is a memoir that is as furious as it is vulnerable, as fierce as it is fragile. Ultimately, Gay wrestles with one of the most complicated kinds of love — namely, self-love.

Get it from Amazon for $11.55+, Barnes and Noble for $13.86+, or find it at IndieBound or your local library.

Sharp Objects may be bleak and gory, but guess what: Sometimes, so is love. This novel, recently adapted as an HBO miniseries, follows reporter Camille Preaker as she goes back to her hometown of Wind Gap to investigate the deaths of two little girls. Just when our heroine comes close to cracking the case, it seems like she might have a shot at love too — with the hotshot detective called in from the city. But Camille obliterates her chance at romantic happiness with an infidelity that exposes her addiction to alcohol and cutting. Flynn creates dark, complex female characters who dare us to confront our own shadow selves, and how the scars we wear on the outsides are nothing compared to the ones we carry inside.

Get it from Amazon for $8.90+, Barnes and Noble for $12.80+, or find it at IndieBound or your local library.

Miller’s The Song of Achilles casts a spell on the classics with a remix of The Iliad — specifically the tragic story of legendary half-god and hero Achilles and the lesser-known Patroclus. The sexual tension between these characters is blistering and Miller takes her sweet time seducing the reader to turn the pages, practically begging for these two star-crossed lovers to come together. But with the Trojan War looming, Achilles and Patroclus must face their own heartbreaking destinies. Miller stays true to Homer’s tale, and anyone familiar with this epic poetry knows that things don’t usually end well for mythological lovers. The gods basically live to break human hearts while sipping nectar from their thrones on Mount Olympus. They binge on human suffering like it’s the original Netflix.

Get it from Amazon for $11.55+, Barnes and Noble for $13.86+, or find it at IndieBound or your local library.

My Year of Rest and Relaxation by Ottessa Moshfegh 9. When a city breaks your heart:by Ottessa Moshfegh Penguin Press, Ottessa Moshfegh

If you’ve been itching to push the limits of the unlikeable female protagonist to a new level, grab this novel and dive in. Moshfegh’s sly and delicious delivery will force you to love (and feel guilty about loving) this nameless protagonist, who emotionally abuses her annoying best friend, and seems to have every advantage in life, but instead devises a plan to pop enough prescription pills to sleep the next year of her life away. The novel captures the deep loneliness of what life in NYC can become and pokes serious fun at the pretentiousness of the art world; Moshfegh also skewers those psychiatrists who prescribe pills as if they were Pez. But the book becomes something so much more than a literary black comedy starring a self-medicating sleeping beauty, and instead unravels the harrowing backstory of a complicated character. The author builds up to an Aristotelian last page that is so surprising, you don’t even have time to realize that by the time you read the last word, she has already ripped your heart of your chest.

Get it from Amazon for $17.68, Barnes and Noble for $20.80, or find it at IndieBound or your local library.

Sometimes a title can really tell you everything you need to know about what’s waiting inside. In five short words, Night Sky With Exit Wounds announces to the reader: You are in for some unbearable beauty. Vuong delivers on his title’s promise and writes about many kinds of heartbreaks, investigating familial and personal histories, exploring both violence and romance. These poems are haunting, generous, and daring. In “Someday I’ll Love Ocean Vuong,” Vuong refers to himself in third-person. This poem will sit with you and your broken heart, but it will not sugarcoat: “Don’t worry. Just call it horizon / & and you’ll never reach it. / Here’s today. Jump. I promise it’s not / a lifeboat.” But Night Sky will never completely abandon you either. “Ocean, don’t be afraid. / The end of the road is so far ahead / it is already behind us … Get up,” he tells himself, and in doing so, speaks to all of us, “The most beautiful part of your body / is where it’s headed. & remember, / loneliness is still time spent / with the world.” Get it from Amazon for $10.87, Barnes and Noble for $14.40, or find it at IndieBound or your local library.

Imagine a disturbing world where all girls are sequestered from society, raised in a twisted finishing school, and bred to become either the perfect wives for powerful men, or a worse alternative — their concubines. Best friends freida and isabel — so undervalued in their world, even their names are lowercase — have always tried to maintain their status as the Top 10 Most Beautiful Girls in school, so they can secure their future as respectable “companions.” But when a group of boys visits the girls in their final year of “training,” isabel suddenly isolates herself from freida, and a secret threatens to tear the two girls apart. But Only Ever Yours is radical because it challenges the idea of “happily ever after,” and O’Neill honors her audience by confronting the dark realities without tying it up in a nice red bow.

Get it from Amazon or Barnes and Noble for $7.99+, or find it at IndieBound or your local library.

Bhanu Kapil spent four years traveling through India, England, and the US, interviewing Indian women of various ages and backgrounds. In a locked room without windows or furniture, the women had a half hour to anonymously respond to 12 personal and philosophical questions — about identity, bodies, family, mortality, and more. (#6 — “Who was responsible for the suffering of your mother?” — would often result in spontaneous crying.) The questions alone are breathtaking, but Kapil’s uncensored answers are even more unforgettable.

Get it from Amazon or Barnes and Noble for $17, or find it at IndieBound or your local library.



I had to read this book twice to figure out how E. Lockhart pulled off such a crafty and evocative narrative. Written in a poetic and mysterious style, this YA novel looks at the unforgettable bond connecting four friends over one July that changes everything. The heartbeat of this story lies in the romance between Cadence, the beautiful granddaughter of the prestigious Sinclair family, and Gat, the “relentlessly interested” boy she’s known almost her whole life but suddenly sees in a new way. Because of a mysterious accident, though, Cady is an unreliable narrator, and the reader isn’t quite sure who or what to believe. We Were Liars seduces you with summer love, a remote island setting, hints of Wuthering Heights, and millions of theories you’ll develop along the way to its utterly destructive reveal. Get it from Amazon for $8.87+, Barnes and Noble for $9.42+, or find it at IndieBound or your local library.

Love and basketball take on a whole new meaning in Alexander’s novel-in-verse about twin basketball stars Jordan and Josh, whose bond of brotherhood is tested when one girl comes between them. While the brothers face competition and jealousy, both on and off the courts, ultimately, this is a book about family and the power of a love you did not even choose. Don’t let the “middle-grade reader” marketing label fool you — the tenderness inside this book, specifically the portrayal of deep love between fathers and sons, will absolutely take your breath away. Get it from Amazon or Barnes and Noble for $8.99+, or find it at IndieBound or your local library.

15. When you're heartbroken but unapologetic: Love Story by Erich Segal Hodder Paperback, By Karen Segal - Own work, CC BY-SA 3.0, commons.wikimedia.org

Though Love Story — published in the ’70s — might have perpetuated one of the most untrue and unhealthy statements ever written about love (“Love means never having to say I’m sorry”), Segal’s novel about a couple who have their meet-cute in a college library (be still my nerdy heart) still manages to pack an emotional punch. It’s a quite a feat, considering that we know from the very first lines that our protagonist’s soulmate isn’t going to be alive by the end of this slim, tearjerker of a book: “What can you say about a twenty-five-year-old girl who died? That she was beautiful. And brilliant. That she loved Mozart and Bach. And the Beatles. And me.” Love Story takes a page right out of Shakespeare’s heartbreak playbook, mixing forbidden love with family disapproval and a beautiful dead girl. Doomed young lovers get the job done every time. Get it from Amazon for $15.62+, Barnes and Noble for $7.99+, or find it at IndieBound or your local library.

So, technically this book is comprised of only .0476% heartbreak, with, as the title describes, 20 poems of love and one song of despair. However, it’s exactly this setup that mirrors the trajectory of idealist love that starts strong and then goes wrong. Famed Chilean poet Pablo Neruda first published these breathtaking poems in 1924 at the tender age of 19, and it remains the best-selling book of poetry in the Spanish language for very good reason. These poems are timeless, accessible, and contain astonishing imagery: “The memory of you emerges from the night around me … cold flower heads are raining over my heart.” One of Neruda’s most famous love poems gets right to the point and begins, “Tonight I can write the saddest lines.” Inside it, Neruda captures perhaps the truest and cruelest ironies of love, the secret of what makes heartbreak so damn heartbreaking: “Love is so short, forgetting is so long.”

Get it from Amazon for $11.05, Barnes and Noble for $11.70, or find it at IndieBound or your local library.

Andrew McMeel