A Greek helmet from the cover of "Song of Achilles"
(Ecco Press)

10 of the Most Heartbreakingly Romantic Books Ever Written

Abandon all hope of a happy ending, ye who enter here. If you’re looking for a sexy beach read, you might wanna find another list. Like in a real world, romance in these books is gonna be rough going. After all, the course of true love never did run smooth. Sometimes it runs in the other direction all together.

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The Great Gatsby

"The Great Gatsby" cover art
(Charles Scribner’s Sons)

I’m coming in hot to say that The Great Gatsby, despite a conspicuous lack of kisses, is one of the greatest romantic novels of all time. It’s really more of a romantic elegy. The romance already happened, and now the characters are looking back upon it. Despite what roaring ’20s Hollywood adaptations would have you believe, the source material’s tone is one of sheer melancholy. It feels like looking at old Polaroids of a party you went to long ago. That’s the point of the book!

The nouveau riche Jay Gatsby is attempting to reignite his old romance with socialite Daisy Buchanan, and this novel provides a gorgeous cautionary tale about why attempting to reflame old passions is never a good idea.

Giovanni’s Room

cover of giovanni's room by james baldwin
(Vintage Books)

Another heartbreaker, Giovanni’s Room is an incomparable work of queer romantic fiction by the late, great James Baldwin. The narrator recounts an old romance he sparked up while in Europe with the gorgeous Giovanni. Taking place at a time when queer men were met with particular stigma, their romance was practically doomed to fall apart from the beginning. And fall apart it does, beautifully, like watching the slow and graceful wilting of a flower. It’s a reflection on the difficulty of love and relationships, no matter one’s sexuality or gender.

The Song of Achilles

The Song of Achilles by Madeline Miller

And the sobbing continues. The Song of Achilles by Madeline Miller is a crushingly beautiful read. Painstakingly revised over the course of a decade, the novel reads more like a long-form poem than prose. It centers around the mythical relationship between Ancient Greek demigod Achilles and his lover Patroclus. Miller reimagines the lovers as a pair of childhood best friends who soon discover that their love for one another is deeper than they once thought. The lovers defy kings, gods, and the stars themselves to stay together to the bitter, prophesied end.

Pride and Prejudice

Pride and Prejudice by Jane Austen

We’re taking a break from all the sad lovers biz to bring you what is widely considered the greatest work of romantic fiction ever written! Jane Austen’s Pride and Prejudice is the ultimate enemies to lovers arc, and begins with the quick-to-judge Elizebeth Bennet and the aloof Fitzwilliam Darcy immediately rubbing each other the wrong way at the fancy English countryside party to which they were both invited. As time passes, the pair begin to let their pride and prejudices (title drop) toward one another go and see the hearts of gold that beat inside both their chests. There’s a reason that this novel has been interpreted for the screen a bajillion times, because it deserves no less.

Call Me By Your Name

The cover art for "Call Me By Your Name" featuring two men leaning on each other
(Farrar, Straus and Giroux)

Uh oh. What is that young twink about to do with that fresh produce? You’re about to find out. Call Me By Your Name is a love story between a teenage boy who falls in love with a graduate student in the summer of 1983 in Northern Italy. While initially reluctant to get the love fires a-burning, the pair’s passions reach inferno levels after spending their summer days together. The novel features a swoon-worthy theme of calling a lover by your own name, treating them as an extension of yourself. And sex with peaches. Witheringly romantic.


Outlander book 1 by Diana Galaldon

The fantasy romance Outlander just works. Who among us hasn’t dreamed of being swept up in the burly arms of an 18th-century Scottish warrior man? After a honeymoon trip to see some ancient standing stones, British nurse Claire Randall is whisked away from her husband through the annals of time! She discovers that she has been transported to the 1700s after coming in contact with one of the stones, and she comes in contact with a highlander who desperately needs her medical knowledge (and tender love) to help his clan survive. Things get even more complicated when Clair meets her future husband’s evil past ancestors, and a wild historical fantasy romp is born.

The Notebook

an empty front porch overlooking a green field

The heartbreak train keeps on rolling. The Notebook tells the story of a pair of lovers over five decades, beginning with their passionately romantic beginnings and ending with the heroine Allie’s eventual Alzheimer’s diagnosis. The details of their relationship are recorded in a notebook, which Allie’s husband Noah reads to her in their final years in an effort to get her to remember him once again. World War II, family tragedies, these two people have been through a lot. It’s a testament to the fleeting nature of youth, and the enduring power of love to keep people young nonetheless.

Morning Glory

The cover art for Sarah Jio's "Morning Glory"
(Putnam Publishing Group)

What is it about World War II that makes for such good romance stories? Morning Glory revolves around a pair of social outcasts in Georgia who find what they need in one another at the beginning of the war. Will Parker is a drifter and ex-con, while Ellie Dinsmore lives a shuttered-up life in her grandparents’ house and is known as “Crazy Ellie” throughout her small town. The strength of the novel lies in its powerful portrayal of the little things. Ellie and Will slowly begin to heal one another simply by living a domestic life together. No big battles or time travel, just the coziness and comfort of love at home.

The Time Traveler’s Wife

"The Time Traveler's Wife" cover art
(‎Harcourt, Brace and Company)

Henry is an artist with some freaky genetics. He time travels. Totally at random. Just disappears and reappears throughout history. One might think that this would make him undatable, but one would be wrong. Clare falls and love with and marries Henry nonetheless, and the novel centers around her struggle to cope with his frequent absence, as chapters alternate between their perpesctives. What makes loving him even HARDER is that whenever they try to make a baby the baby ends up time traveling right of her … Yes it’s messy. No it doesn’t have to make sense. It’s just high-octane romantic longing. What we’re all here for.

Written On The Body

"Written on the Body" cover art
‎(Vintage Contemporaries)

Written On The Body is unique for its portrayal of its narrator, who is assigned neither name nor gender. They begin an affair with a married woman and deal with the complex emotional fallout that results. The strength of the novel lies in its gorgeous prose, with lines like “the world will come and go in the tide of a day but here is her hand with my future in its palm.” Banger. In a genre so often defined by gender roles, Written On The Body‘s non-binary narrator forces the reader to forego such notions and view love as a universal experience undefined by gender. We all love in the same way, after all.

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Jack Doyle
Jack Doyle (they/them) is actually nine choirs of biblically accurate angels crammed into one pair of $10 overalls. They have been writing articles for nerds on the internet for less than a year now. They really like anime. Like... REALLY like it. Like you know those annoying little kids that will only eat hotdogs and chicken fingers? They're like that... but with anime. It's starting to get sad.