Jacob Brogan writes about culture and technology. He holds a PhD in English Literature from Cornell University, has taught at Georgetown and is currently researching a book on lovesickness.

(Jonathan Newton/The Washington Post)

For all but the most happily coupled, Valentine’s Day disappoints, an annual reminder that longing for love always means living with heartbreak. As it happens, the literature of love teaches a similar lesson. Maybe that’s why the loveliest texts about love are those that shatter us. Here is a collection of readings for those days when desire leaves you wanting.

“Fragment 31”, Sappho

Almost without exception, Sappho’s writing comes to us in fragments. Though that’s one of the great tragedies of literary history, it’s also strangely apt, as it captures the endless irresolution of her desires. In “Fragment 31,” we stumble on the poet contemplating another couple. “Greener than grass / I am and dead — or almost / I seem to me,” Sappho sings as she watches them, feverishly in love with the very idea of loving. Read it in Anne Carson’s remarkable translation in her collection “If Not, Winter.”

“Was She Pretty?”, Leanne Shapton

Deceptively complex and uncommonly elegant, “Was She Pretty?” is a series of gorgeous line drawings, most of men and women. Each is accompanied by a sentence or two describing something — some spare fact — about someone’s ex. “Hugo’s ex-girlfriend Katya was 70 percent deaf. She had a gentle way with children and animals,” reads one page. “Katya’s ex-boyfriend never stopped sending her postcards,” Shapton writes on the next. Together, these brief encounters with the other tell a story about the difficulty of accepting that those we love have loved before — and of recognizing the ugly truth that they may love again.

“A Lover’s Discourse,” Roland Barthes

Love was a system for the French critic Roland Barthes, one made up of awkward evasions, unbearable desires and occasional ecstasies. Unable to confront that system in its totality, he shatters it in “A Lover’s Discourse,” studying its pieces and parts in a series of kaleidoscopic philosophical vignettes. Here you’ll find enigmatic essays on languor and love letters, on magic and monstrosity.

“Tear It Down,” Jack Gilbert

“By insisting on love we spoil it, get beyond / affection and wade mouth-deep into love,” Gilbert writes in “Tear It Down,” a devastatingly raw poem. If we want to love, Gilbert’s poem says, we must shred it and celebrate the pieces.

“Shortbus,” John Cameron Mitchell (dir.)

Though it is notorious for its unsimulated sex scenes, Mitchell’s film is ultimately a story about self-love in the face of self-loss. Largely unbound by convention, its beautiful, sad characters learn to care for one another by confronting their own emptiness. As the film’s Justin Bond declares in one early orgiastic scene, “Voyeurism is participation,” but sometimes being a part of something means standing apart. And sometimes, Mitchell tells us, that’s okay.

The Navigators,” Marilyn Hacker

Few poems capture the complexities of love quite so fully as “The Navigators,” which narrates the erotically charged relationship that Hacker and her then-husband, Samuel R. Delany, had with a homeless man — “an incubus / whom we have filled with voyages.” Delany explores the same experience in his similarly rich memoir “The Motion of Light in Water,” where he fixates especially on the final lines of Hacker’s work. There, facing the dissolution of a bond that almost destroyed her, Hacker offers one last entreaty, asking those she’s lost to “initiate the change that moves the peripheries of love.” For a moment, heartbreak and hope are one and the same.

The Symposium, Plato
Plato frames the Symposium as a series of speeches about love delivered by ancient Athenian luminaries — Phaedrus, Aristophanes, Socrates and others. Though their speeches are sometimes ribald, they build toward the dry Socratic conclusion that love involves a gradual process of distancing ourselves from the body and its passions. But instead of finishing on that high note, it ends with everything thrown out of whack as Alcibiades, Socrates’ former student, drunkenly interrupts the proceedings to complain that his mentor refused to have sex with him. Silly, sweet and sad all at once, Alcibiades’ speech is a reminder that every idealistic philosophy of love is inadequate to the actual torment of loving.

Meet 10 incredible couples and hear the fascinating stories behind the start of their relationships. (McKenna Ewen/The Washington Post)