Spoiler Alert: Reading this post and following the embedded links might spoil the endings of these books.

You could celebrate Valentine’s Day by reading one of the many heartwarming stories of love triumphant: Pride and Prejudice, perhaps, whose protagonists find their way to love despite their eponymous flaws; or Much Ado About Nothing, in which love overcomes obstacles both cruel and comical. However, if your plans for February 14 involve curling up with a book rather than a significant other, perhaps a story of love lost, betrayed, or otherwise defeated would be more appropriate. If you are in need of some literary angst on this typically romantic holiday, here are some ideas to get you started.

Ulysses

To some extent, this immense novel by James Joyce is based on Homer’s epic poem The Odyssey. The warrior Odysseus becomes the advertising agent Leopold Bloom; years of journeying across the Mediterranean become a day of wandering the streets of Dublin. While some of these diminished parallels reveal the importance of the mundane, the epic in the everyday, others strike a more melancholy note—especially the relationship between Bloom and his Penelope, Molly. Odysseus returns home to a faithful wife, who has successfully fought a battle of wits with her would-be suitors, but Bloom returns home the same as he left it: a cuckold. Even the superficially affirmative tone of Molly’s concluding reflections reveals the seeds of her discontentment: "..and I thought well as well him as another..."

Rabbit, Run

John Updike examines marital (and existential) unrest in more detail with his portrait of the young Harry "Rabbit" Angstrom, a man who feels trapped in his marriage. Faced with an unhappy wife pregnant with the couple’s second child, Rabbit flees from home, spending the remainder of the book vacillating between his commitment to Janice and his new love for another woman. Despite tenuous attempts at reunion, the novel ends with restless ambiguity rather than romantic triumph. “It’s too [expletive] late to be happy.”

Lancelot

Although they are no more tragic, infidelity’s consequences are certainly more dramatic in this novel by Walker Percy. Learning that his wife has been unfaithful to him drives Lancelot Lamar to blow up his own house, with his wife and her lover (as well as himself) inside. While he survives the explosion, he remains confined in a “Center for Aberrant Behavior,” where he muses distressingly on the nature of love and its state in modern society. "Did I love her then, that day I speak of? Love. No, not love. Not hatred, not even jealousy. What do those old words mean?"

1984

George Orwell doubles this romantic betrayal, albeit in a very different context. The relationship between Winston and Julia, built mainly on their mutual disdain for the totalitarian state in which they live, crumbles when they are separately imprisoned and confronted with the threat of torture and death: each begs to be spared, pleading that the other suffer the torment instead. The lovers both live through their respective incarcerations, and they even manage to see each other again. However, this terrible revelation of their underlying selfishness has extinguished every ember of their passion. "Under the spreading chestnut tree / I sold you and you sold me…"

Brave New World

Often compared to 1984, Aldous Huxley’s dystopian classic is arguably even more depressing in its portrayal of humanity and its potential future. Just one aspect of his darkly humorous commentary involves the character of John, also called “the Savage”: a man who is raised outside of society only to be thrust into it as an adult, to much chaotic effect. His ill-fated, Shakespeare-infused idealization of Lenina Crowne gradually builds to a sharp, morbid critique of romanticism. "Did he dare? Dare to profane with his unworthiest hand that… No, he didn’t."

 

 

 

 

The Great Gatsby

A similar romanticism gives F. Scott Fitzgerald’s most famous work its emotional weight. Gatsby’s love for Daisy endures time, distance, and her marriage to another man; yet ultimately, this passionate personal idealism is crushed by bleak reality, leaving his dreams unfulfilled."Gatsby believed in the green light, the orgiastic future that year by year recedes before us. It eluded us then, but that’s no matter—to-morrow we will run faster, stretch out our arms farther….And one fine morning——"

 

 

 

 

 

Brighton Rock

Even more depressing than the flawed romantic notions of Gatsby and the Savage is the heartless calculation of Pinkie, the young English gangster from Graham Greene’s 1938 novel. Cinematic flashbacks reveal the roots of Pinkie’s twisted nature—most disturbingly, his aversion to all forms of love. Despite this, however, Pinkie agrees to marry a young waitress named Rose rather than risk her telling the police about the gang’s various murders. In doing so, he both drags her into his violent world and causes further torment to his own sick soul. "A ring…what sort of ring? We aren’t married. Don’t forget that. We aren’t married."

 

 

 

A Farewell To Arms

If none of these titles are sufficiently depressing, you can always turn to Ernest Hemingway. Gatsby’s grim ending might contain some trace of tragic romance; Brighton Rock’s darkness at least affirms some vision of love by bleak contrast. But the sudden, brutal conclusion to Frederic and Catherine’s relationship offers not even slight consolation. This modernist memento mori is a surefire remedy to a case of mid-February sentimentality. “That was what you did. You died. You did not know what it was about. You never had time to learn.”

 

 

 

 

Happy Valentine’s Day!