10 depressing book recommendations for Valentine's Day

You probably already know this, but I love love, and I love love stories. In particular I like unhappy love stories (I always joke that I’m more obsessed with divorce than I’ve ever been with marriage). So, in honor of Valentine’s Day, some not-so-happy book recommendations:

  1. Heartburn by Nora Ephron

I just finished this yesterday. It’s autobiographical fiction based on Nora Ephron’s divorce from her second husband, Carl Bernstein. He cheats on her while she’s seven months pregnant (!) and their relationship dissolves quickly, which is obviously a tragic premise, but guys: the book is so, so, funny. I have to confess that I haven’t read that much Nora Ephron beyond I Feel Bad About My Neck before, though I obviously have watched Sleepless in Seattle, and I was blown away by how witty and hilarious this book is (it has been described as “savagely funny”). It’s also casually studded with recipes that I’m excited to test out (cheesecake, key lime pie, linguine). Excerpt:

Vera said: “Why do you feel you have to turn everything into a story?”

So I told her why:

Because if I tell the story, I control the version.

Because if I tell the story, I can make you laugh, and I would rather have you laugh at me than feel sorry for me.

Because if I tell the story, it doesn’t hurt as much.

Because if I tell the story, I can get on with it.

  1. Why Love Hurts by Eva Illouz

For a sociological view of modern love! Personally, I find it very reassuring to realize that what you thought were personal neuroses are actually symptoms of large-scale societal changes that have emerged in the past 50 to 100 years as a result of the deregulation of marriage and sex. Male reticence, commodified sexuality, women feeling pressured to start families: this book explains it all.

What is properly modern in modern romantic suffering are: the de-regulation of marriage markets (chapter 2); the transformation of the architecture of choice of a mate (chapter 3); the overwhelming importance of love for the constitution of a social sense of worth (chapter 4); the rationalization of passion (chapter 5): and the ways in which the romantic imagination is deployed (chapter 6).

  1. I Love Dick by Chris Kraus

I’ve never been remotely interested in Karl Ove Knausgaard, but I’ve loved Chris Kraus forever. Kraus, of course, is the patron saint of smart misfit girls everywhere and I Love Dick is the book on romantic obsession. Kraus in the book, who is basically just Chris Kraus in real life, is a failed filmmaker in a sexless marriage who meets a friend of her husband’s, Dick, and becomes completely obsessed with him. It’s one-sided. She and Sylvere Lotringer, her husband, conspire to start sending him her letters. I Love Dick is essentially a compilation of all these intense, rambling, wonderful letters (she “harasses him with intellectual valentines”). This is auto-fiction and the real-life Dick was extremely upset when she published the book, but putting ethical qualms aside: the letters, the letters are so good. Some choice quotes:

If seduction is a highball, unhappiness has got to be the booze.

I’m moved to talk to you about art because I think you’ll understand and I think I understand art more than you—

—Because I’m moved in writing to be irrepressible. Writing to you seems like some holy cause, ‘cause there’s not enough female irrepressibility written down. I’ve fused my silence and repression with the entire female gender’s silence and repression. I think the sheer fact of women talking, being paradoxical, inexplicable, flip, self-destructive, but above all else public is the most revolutionary thing in the world. I could be 20 years too late but epiphanies don’t always synchronize with style.

I can’t tell you how many times I’ve reread this book. Probably 10 plus? I still get chills every time.

  1. Bluets by Maggie Nelson

This is a singular book, and crying while reading Bluets right after a breakup is an experience everyone should go through at least once. It’s a book about heartbreak and a book about the color blue; it’s heavily referential; it’s written in beautiful fragments.

An excerpt:

  1. In any case, I am no longer counting the days.

  2. I want you to know, if you ever read this, there was a time when I have had you by my side than one of these words; I would rather have had you by my side than all the blue in the world.

  1. Ada or Ardor by Vladimir Nabokov

Oh, you thought I was going to recommend Lolita, didn’t you? Well, 1) putting Lolita on a list of Valentine’s Day book recommendations is just asking for trouble, 2) I’m not that much of a cliche, fuck you, and 3) Ada or Ardor is the better book. Incest over ephebophilia. Good job, Nabokov! Anyway, Ada or Ardor is about…. oh god. Okay, Ada or Ardor is about Van Veen and his ostensible cousin, Ada, who meet when she is 11 and he is 14, and commence a lifelong love affair. The story is set in the 19th century, in an alternate version of earth called Demonia or Antiterra. There are lots of trilingual puns. I suggest reading an annotated version of the book, otherwise you’ll just miss everything.

“I am sentimental,’ she said. ‘I could dissect a koala but not its baby. I like the words damozel, eglantine, elegant. I love when you kiss my elongated white hand.”

This book is absolutely the worst, by which I mean it’s perfect and it’s perfection has messed me up forever. Probably you shouldn’t read it.

  1. Milk Fed by Melissa Broder

I love Melissa Broder’s writing and multiple people have told me they’re obsessed with her essay collection So Sad Today, so I know you guys share the sentiment. Milk Fed came out a week or so ago and it’s about an anorexic woman who falls in love with a zaftig Jewish woman who teaches her to love food and sex again. It’s really funny:

My therapist in Los Angeles, Dr. Rana Mahjoub, wore sensible clogs and said insight-adjacent things like “put on our oxygen mask before helping others,” but I din’t entirely respect her because she accepted my insurance. How good could she be if she was willing to deal with Blue Shield?

It’s also some of the best writing I’ve encountered about what it’s like to have an eating disorder: the obsessive tracking and restriction, the preoccupation with food. The sex scenes are great and there’s a lot of descriptions of various bodily functions. Highly recommend.

  1. Heart Berries by Terese Mailhot

I’m going to start off with an excerpt from the second chapter of Heart Berries:

You had a hard-on for my oratory. Some of my stories were fabricated. I had authority—a thing that people like you haven’t witnessed. It comes from a traditional upbringing and regarding my work as something more sacred than generations of effort or study. It’s something on a continuum, so far reaching you know it came from an inhuman place. Story is inhuman and beyond me, and i’m not sure you ever recognized that. You knew to be excited in proximity to my power.

Mailhot is a First Nations Canadian author and her writing is steeped with the knowledge and pain she’s inherited. Heart Berries is a short and incredibly powerful memoir. It’s brutally honest. It’s a love story. It’s also terrifying:

Love is tactile learning, always, first and foremost.

When you loved me it was degrading. Using me for love degraded me worse. You should have just fucked me. It was degenerative. You inside me, outside, then I leave, then I come back, get fucked, you look down at me and say, “I love you, I love you.” I go home and degenerate alone.”

  1. What Belongs to You by Garth Greenwell

Garth Greenwell writes the best highbrow sex scenes. This is not an original observation: literally every time he’s mentioned in the New Yorker or w/e the writer is like… Garth Greenwell writes great sex scenes. Greenwell himself: “I wanted something 100% pornographic and 100% high art.”

The narrator of What Belongs to You is an American teaching at the American College of Sofia in Bulgaria (Greenwell himself did the same). He meets a younger male prostitute, Mitko, and begins a relationship of sorts with him. This doesn’t sound like the most romantic premise, and it is a dark book, but the prose is so lyrical, so dense and beautiful, and the sex scenes manage to be both pornographically explicit and yet incredibly well-written.

  1. Mariette in Ecstasy by Ron Hansen

This is a story about a young girl who joins a convert and experiences religious ecstasy. I would describe it as a love story between her and Christ. The writing is meticulous and otherworldly. It’s a very simple novel, but I felt completely transported while reading it.

"We try to be formed and held and kept by him, but instead he offers us freedom. and now when I try to know his will, his kindness floods me, his great love overwhelms me, and I hear him whisper, Surprise me.”

  1. The Light of the World by Elizabeth Alexander

I realize that the none of the relationships portrayed in the books I’ve recommended are particularly aspirational and many of them are rooted more in obsession than actual healthy romantic love, but fear not: The Light of the World is about Capital-R Real Love. It’s a memoir by a professor of poetry at Yale about the sudden death of her husband. Here’s her description of their first meeting:

Or it began when I met him, sixteen years before. That was always a good story: an actual coup de foudre, a bolt of lightning, love at first sight. I felt a visceral torque, I would tell people, a literal churn of my organs; not butterflies, not arousal; rathe, a not-unpleasant rotation of my innards, as never before. Lightning struck and did not curdle the cream but instead turned it to sweet, silken butter. Lightning turn sand into glass.

She resurrects him in these pages, renders him vibrant and alive again. This is a memoir about grief, art, love, and food. It’ll make you cry.


Please tell me if you’ve read any of these books, and what you think of them! Also: any Valentines’ Day books recommendations for me? I’m always looking.