12 of the Most Unforgettable Books About Doomed Romances

We all enjoy a love story with a happy ending, but we also know that life isn’t perfect. Thanks to the recent success of films like Nosferatu, Gothic romance is having a moment. And in a way, it makes sense, as tales about star-crossed lovers and heartbreak are often just as enjoyable in their own way as schmalzy feel-good alternatives, perhaps even more so. After all, would Romeo and Juliet have remained so enduring if the two protagonists had skipped off into the sunset?

Such stories serve to remind us to be grateful for what we have, and even justify a good, clean crying session. The relationships you’ll find within these types of romance books are typically defined by cruel acts of fate and seemingly unsurpassable social divides. You won’t find any real happily-ever-after, fairytale outcomes in any of the works selected here—instead, just crippling passions and poorly made choices that often drive the lovers further apart. 

Not all of the books listed below end with tragedy, but, as is often the case in real life, no tale unravels without its fair share of sorrow and woe. From ghastly ghosts and terrible choices to familial discord and awkward sexual awakenings, this round-up has all the ill-fated lovers you could wish for ahead of Valentine’s Day.

1. Wuthering Heights by Emily Brontë (1847)
2. The End of the Affair by Graham Greene (1951)
3. I Too Had a Love Story by Ravinder Singh (2008)
4. Jude the Obscure by Thomas Hardy (1895)
5. A Song of Achilles by Madeline Miller (2011)
6. Anna Karenina by Leo Tolstoy (1878)
7. Desperate Characters by Paula Fox (1970)
8. The Fault in Our Stars by John Green (2012)
9. The Remains of the Day by Kazuo Ishiguro (1989)
10. Of Human Bondage by W. Somerset Maugham (1915)
11. The Magus by John Fowles (1965)
12. In the Dream House by Carmen Maria Machado (2019)

Wuthering Heights by Emily Brontë (1847)

This is the sole novel by Emily Brontë, one of a remarkably talented trio of siblings alongside sisters Charlotte and Anne. Wuthering Heights contains all the classic elements of the doomed romance novel: forbidden love, awful misunderstandings, jealousy, revenge, and tragedy. It was initially published under the pseudonym Ellis Bell and caused quite a storm amongst contemporary critics thanks to the brutal actions and perceived inhumanity of its protagonists, Cathy and Heathcliff. Yet the strange and dark charm of the book was evident from the start, and it’s gone on to become one of the most revered tragic love stories of all time. Plus, there’s the little matter of Kate Bush’s enduring song and accompanying video.

The End of the Affair by Graham Greene (1951)

Considered one of Greene’s best-loved works, this gripping read is set in London during World War II as the Blitz—a singular period when the city’s population united under the relentless bombing of the Luftwaffe—rages on. The novel’s protagonist, writer Maurice Bendrix, begins an affair with Sarah Miles, the wife of a civil servant. When Sarah abruptly ends the relationship, Bendrix makes the fateful decision to hire a private detective to uncover the reason why, an act that results in a climactic revelation. The plot takes inspiration from Greene’s own affair with the politician Catherine Walston.

I Too Had a Love Story by Ravinder Singh (2008)

Indian author Ravinder Singh’s autobiographical debut was a big hit in his native country when it was first published, and with good reason. Protagonist Ravin meets Khushi online. They fall in love, but the day before an arranged real-life meeting, tragedy strikes. Where other novels might finish at this point, this is only the beginning of Ravin’s heartbreaking and tumultuous story. Singh examines the grief of lost love with endearing poignancy and throws in a compelling dash of mystery for good measure. In these pages, the fragility of human life is laid bare with stinging familiarity.

Jude the Obscure by Thomas Hardy (1895)

Hardy was never exactly known for the cheeriness of his works, but this, the 13th and final novel the author completed, reaches new depths of bleakness and despair. The titular Jude Fawley nurses dreams of studying at the prestigious university in Christminster (a thinly disguised Oxford), but his working-class background makes this impossible. This is the premise for a tale of broken dreams, unhappy marriages, and a yearned-for relationship which, just when it seems set to blossom into happiness, ends in the most harrowing manner imaginable. Hardy’s first wife, Emma Gifford, is believed by some to be the inspiration for Sue Bridehead, and it’s a novel that definitely comes with a hefty trigger warning.

A Song of Achilles by Madeline Miller (2011)

Miller turned to Greek legend as inspiration for this vivid reimagining of the Trojan War and the romantic relationship between the male heroes Patroclus and Achilles. The author spent 10 years working on the novel, making good use of her passion for Greek mythology and her training as a Latin and Greek classics teacher. She scooped the Orange Prize for Fiction in 2012 as a reward. As you would expect, the setting is fantastic, and the larger-than-life events are engrossing. Still, it’s Miller’s teasing out of emotion that sticks in the mind. You don’t have to be a fan of ancient literature to enjoy this memorable book.

Anna Karenina by Leo Tolstoy (1878)

Initial reviews for Anna Karenina were decidedly mixed, but Tolstoy’s 1878 work is now widely regarded as one of the greatest novels of all time. Tackling it may seem an intimidating prospect, as it runs to 800 pages (and more than 350,000 words). Once you allow yourself to sink into its world, however, you will likely find yourself lost in an epic story that strikes on perennial themes of familial problems and social class discontent. It follows around 20 main characters, too, but there’s a tragic love story at the heart of it that is sure to stick out if you haven’t already crossed this classic off the TBR list.

Desperate Characters by Paula Fox (1970)

The best authors can conjure high emotion and deep meaning from the most ordinary of circumstances. Paula Fox’s evocative take on 1970s middle-class American life follows Sophie and Otto Bentwood, a childless married couple, across the timespan of a single weekend. Things start off innocuously enough—Sophie gets bitten by a stray cat—but progressively spiral from there, creating a mounting sense of existential dread that ramps up into sheer psychic tension and ending in an outburst of rage stemming from years of quiet desperation. Despite the heavy themes here, Fox is actually best known as a consummate writer of children’s fiction, even winning the coveted Hans Christian Andersen Award in 1978.

The Fault in Our Stars by John Green (2012)

John Green’s heart-wrenching 2012 novel draws its title from an evocative phrase in Shakespeare’s Julius Caesar, and follows the stories of 16-year-old Hazel and 17-year-old Augustus, who meet via a cancer patient support group. It’s a brave set-up and subject from Green, a former Mental Floss writer who spent time in his youth working as a student chaplain at a children’s hospital. The book places a lot of importance on the transformative effects of literature, though readers are likely to weep over the seemingly inevitable sad ending. There is, at least, a positive message to be taken and a plethora of highly moving moments along the way.

The Remains of the Day by Kazuo Ishiguro (1989)

Nobel Prize winner Kazuo Ishiguro’s moving novel explores repressed emotions, misplaced loyalty, and domestic service through the eyes of Stevens, a butler during the 1920s and ’30s. An aching poignancy permeates the relationship between Stevens and housekeeper Miss Kenton, which teeters on the verge of full-blown romance but never achieves it. The author makes masterful use of the setting, and Lord Darlington’s dubious role as a Nazi sympathizer adds spice. Still, it’s the tragic tension between Stevens and Kenton that lingers in the memory.

Of Human Bondage by W. Somerset Maugham (1915)

It may be more than a century old, but the lessons and warnings to be found in Maugham’s classic novel still resonate today. Young Philip Carey moves from his rural home to the city of London to pursue a career as a doctor but gets sidetracked by the bohemian ideal of artistic expression. He meets Mildred Rogers, a woman who embodies everything Carey is not—rude, materialistic, and uneducated. Despite this, or perhaps because of it, Carey spirals into a demeaning obsession that comes close to ruining his life. The book contains many autobiographical elements. Like his protagonist, Maugham lost his parents at a young age and was raised by his aunt and uncle; he also studied medicine.

The Magus by John Fowles (1965)

The second novel by English author John Fowles is a nerve-shredding ride that will twist your brain into so many knots and put your soul through such a rinsing that you might begin to doubt the words before you on the page. It starts simply enough: Oxford graduate and playboy Nicholas Urfe enters into a relationship with an Australian woman but soon grows bored with life and love, so he seeks a way out. He accepts a teaching post on a small Greek island and, once there, befriends a mysterious recluse and his beautiful ward, Lily. After Urfe becomes infatuated with Lily, what follows is an astounding game of bluff and betrayal. Fowles drew loosely from his own experiences on the island of Spetses for this work, which was later adapted for film in 1968 starring Michael Caine and Anthony Quinn.

In the Dream House by Carmen Maria Machado (2019)

Machado’s striking autobiographical work is a masterstroke in sensitivity, artistry, and bravery. In it, she recounts her experiences as a student at the Iowa Writer’s Workshop, where she met a female Harvard graduate with whom she became besotted. What follows is a downslide from initial, though wary, happiness to darkness as fault lines open and abusive, problematic behavior comes to the fore.

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