ten books about unrequited love

A new series! My ten picks for various literary categories. First up: unrequited love.

That sweet and heartbreaking feeling has been a staple trope of literature for centuries. Will it ever get tired? As long as it feels so good to see Anne Eliot and Frederick wonder if it’s too late (Persuasion), Gatsby to repeatedly torture himself over Daisy (The Great Gatsby), or most characters in García Márquez novels to depressingly waste their lives after their love betrays them (Love in the Time of Cholera), I highly doubt it! The list I’ve put together here has just some of these stories, some of them are favorites. If I’ve left your favorite out, don’t blame me. I’m not in charge around here. Let’s begin!

11. Crime and Punishment by Dostoevsky
I’m kidding. This is a top ten list! But I ask you: isn’t the whole point of this book that Raskolnikov is in an unrequited relationship with his pre-murderous sanity? After 570+ pages, I’m tempted to say yes.

10. Le Morte D’Arthur by Thomas Malory
I read this classic last summer and let me just say, is there anything more romantic than the forbidden love between Lancelot and Guinevere? But at least they loved each other, even if they couldn’t be together. Camelot’s real Lady of Unrequited Love in this story is Elaine of Astolat, who shows her love for Lancelot by nursing him back to health after an ill-fated jousting match. He splits and she dies. But in a decidedly modern move, Elaine got the last word: she wrote a letter dogging him for being a dick and blaming him for her death, leaving instructions for a very public funeral flotilla of shame. And so Lancelot loses another (albeit it wetter) jousting match. Medieval badassery.

9. Othello by Shakespeare
Rodrigo loves Desdemona. Othello loves Desdemona but thinks she loves Cassio. Desdemona actually loves Othello. Iago loves Othello and stirring shit but hates everyone else, especially Desdemona and Cassio. Rodrigo kills Cassio (thanks, Iago). Othello kills Desdemona. Then himself. Had anyone actually bothered to ask Desdemona and Cassio who they actually loved, we might actually have a comedy on our hands instead of the fucking terrible tragedy that is the entirety of Acts IV and V. But you know who didn’t die? Iago. Using unrequited love as the ultimate weapon, Iago got away with murder. Three times. As if we needed any more proof that unrequited love is the absolute worst. Tragedy, indeed.

8. Les Misérables by Victor Hugo
Eponine, Eponine, Eponine. How fucking, well, miserable. You were never as young, or beautiful, or clean as Cosette and, as much reason as you have to hate her, you love Marius so much you’re willing to be his go-between. Girl love boy. Boy loves other girl. Boy asks first girl to help him build a relationship with second girl. First girl agrees then dies. And before we move on, let’s remember Cosette’s mom, Fantine. In love with Félix, who abandons her and her child, and then dies. (I’m sensing a theme here.) Love. Isn’t it beautiful?

7. The Sun Also Rises by Hemingway
Poor Jake. In love with the gorgeous, gregarious, and incredibly flirtatious blonde, Brett. Jake returns from the war wounded and his wounds mean he’ll never be able to satisfy Brett. Or any other woman, if you’re catching my drift. So instead he watches her score man after man after man: his college friend, her actual fiancé, a young matador. When everything comes to a head and the shit gets real, Brett crawls back to Jake, but too much has gone on, and Spain isn’t as beautiful as Paris. Something like that. Then they talk about what could have been and that’s that. The end. This one actually made me really sad. Jake seems like a really sensitive guy. Isn’t that how it always is? The good ones chase after the promiscuous blonde only to be left in the dust while the reader at home is wishing she could shrink herself into the pages of a book?

6. Enduring Love by Ian McEwan
If you know this novel, you’re probably going, “Wtf.” I know. That’s what I feel about this book too. When rescuing a boy who crashes his hot air balloon (I know), Jed meets Joe, develops a case of erotomania, and spends the rest of the novel in an increasingly concerning manipulative relationship with Joe and his wife, Clarissa. Just a few highlights from this insane fever-dream: Jed stalks Joe, showing up at his house and various place around the town where Joe was; Jed tried to convince Joe on multiple occasions to admit that something “passed between them” during the rescue; Jed shoots at Joe in a crowded restaurant and then pretends to save him; Jed holds a knife to his own neck in a very misguided attempt to get Joe to forgive him for the shooting; Joe ends up shooting Jed in the arm after buying a gun because he feared for his own safety from Jed. I mean, I love a good gay love story as much as the next gal, but this story is truly what unrequited love nightmares are made of.

5. I Capture the Castle by Dodie Smith
I don’t think there is a single character in this novel who isn’t in love with someone who is in love with someone else. Cassandra is in love with Simon, who’s in love and engaged to Cassandra’s sister, Rose, who’s in love with Simon’s brother, Neil. Simon and Cassandra have a tryst, Rose and Neil pretend to hate each other, and in the end Rose and Neil elope and Simon proposes to Cassandra, who refuses him because she’s convinced he’s still in love with Rose. Did you follow that? Me either. This is an amazing book though, and I highly recommend it.

4. Mansfield Park by Jane Austen
To be honest, I could have substituted almost any other novel by Jane Austen and still have been on-theme. I guess she just really loved making her readers feel absolutely desperate. But it’s Mansfield Park that really pulls out the win for me. Fanny and Edmund are both dreamy people, but she’s poor and he’s rich and if there’s anything we know about Regency England it’s that people from different social classes can’t get together before at least 200 pages in to a book. In all seriousness, though, Fanny Price is one of my absolutely favorite Austen characters of all time. She is sweet and strong and clever. People somehow can’t see it and treat her like shit. But when Edmund *finally* allows himself to admit that he’s in love with and has been in love with Fanny for years, we have an incredibly satisfactory ending to an incredibly frustrating story.

3. Lolita by Nabokov
I read Lolita with a mix of horror and the kind of interest you feel when driving by a car crash; I wanted to look away but I absolutely could not stop reading, despite feeling like the biggest creep in town. Lolita lives up to it’s hype, for sure. Humbert moves in on his landlady’s twelve-year-old daughter, Dolores, nicknamed Lolita. After getting caught, and the universe giving Humbert the biggest pay day when his landlady dies, Humbert becomes Lolita’s guardian. He ends up drugging her to sedate her enough so that he can rape her, but he didn’t use enough of the drug. Apparently that didn’t matter, because the next morning Humbert and Lolita begin a sexual relationship that lasted for several years, him giving her money in exchange for sexual favors. And the world collectively shudders. The car crash continues when Lolita runs away, gets pregnant, and Humbert kills a guy in revenge. As fucked up as it is, I’ve always read Humbert the Pedo’s life as a one-way ticket to Unrequited Pedophilia City. Lolita truly is one of literature’s most tragic characters.

Ok, let’s shake that off, shall we?

2. The Awakening by Katie Chopin
On the surface, it might not be obvious that The Awakening is a story about unrequited love, but I absolutely think it truly is. Of course, there are a lot of themes (female sexuality, motherhood, gender roles, loneliness) but what stayed with me long after I first read this was the realization that Edna was dealing with grief over the loss of a life she thought she had and grief at the loss of the life she realized she wanted. All of us have a vision of who we are and what we want our lives to look like. We develop a strong connection with that vision, a love for that vision, and we (often naively) never imagine that vision won’t materialize. The tragedy of Edna’s story is she had the life she wanted in sight and just like that, it was gone. Her family, her children, her husband, her lover, her life, were all taken from her. I don’t want to spoil this incredible book for you, so I won’t say more. Read this, please. Please.

1. Jane Eyre by Charlotte Brontë
If you know me at all, you know that this is my favorite book of all time. There is something about this story that I will never tire of; I try to read it once a year. Everything about this book is steeped in love and disappointment. But it gives me hope. Jane was plain, small, and insignificant but she was strong, true to herself, and principled. Rochester was damaged, destroyed by a life that went wrong, angry, and mean, but he let himself love even when he knew it was pointless. And they found each other. After years of pain for both of them, after miles of separation, after betrayal, despite the attentions of other people, they found each other. I wish I could go back and read Jane Eyre for the first time. There’s nothing like the feeling that they would never be together; it’s the reason unrequited love is such an aching feeling. If Jane and Rochester can love each other, there’s someone out there who can love us. It hurts to feel unloved, but there’s always hope.

And there we have it. Books about unrequited love, the classic stories that make this very powerful ache feel like everything you’ve ever wanted.