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Fleishman Is in Trouble makes you care about its women by hiding them in plain sight

Taffy Brodesser-Akner’s first novel builds on the roots of her empathetic celebrity profiles.

Fleishman Is in Trouble, a book by Taffy Brodesser-Akner. Random House
Constance Grady is a senior correspondent on the Culture team for Vox, where since 2016 she has covered books, publishing, gender, celebrity analysis, and theater.

Once, in a fit of intellectual and cultural ambition when I was in college, I decided to make my way through the canon of great contemporary literary authors — or, at least, the canon as I understood it from skimming my way through book reviews and looking at which books got adapted for Oscar-bait movies. With a ready will and an open heart, I waded into the bookshelves at Barnes & Noble and commenced reading, and when I eventually emerged several weeks later, there was but a single thought in my head:

I could not stand to read another book about a middle-aged man who is divorcing his shrewish wife and is also having a bunch of kinky sex with an enigmatic young woman, only it turns out that, while she is extremely hot, she just doesn’t understand him. Her hot young feeble lady brain just isn’t up to it.

I could not stand to read another book with that plot, and yet in book after book after book, it was all I could find.

It was bewildering. How was it possible that in this mysterious adult world of contemporary literary fiction, everyone was pretending that this divorced guy story was still interesting after they had heard it more than once? Why was everyone acting as though it was unique or exciting or worth paying attention to over and over and over again? How were they not embarrassed for all those men? Did I just not get it? Maybe those men secretly were fascinating, and there was something wrong with me for not seeing it? After all, I had a feeble young lady brain, too.

Eventually I did find other contemporary literary fiction, mostly written by women, that was about things besides divorce. Still, ever since those early days of floundering through page after page of men’s midlife crisis sex fantasies dressed up as important books, I have regarded all big divorced guy novels with a certain skepticism.

So when I heard the premise of Fleishman Is In Trouble, the hot debut novel of the season, about a New York man getting a divorce and exploring the brave new world of app-based dating, I was not immediately entranced. “This again?” I thought. Weren’t we past that? Hadn’t we all finally, mostly, at long last moved on?

Still, Fleishman was by Taffy Brodesser-Akner, who has written the smartest and most empathetic celebrity profiles I’ve ever read. She’s a writer who knows how to find the humanity in Gwyneth Paltrow’s perfection and Jonathan Franzen’s anger. I had to give it a try.

And I’m so glad I did, because it turns out that Fleishman Is In Trouble is not actually about Toby Fleishman, the doctor divorcé-to-be with his apps full of women. Toby is not at all the point. Fleishman Is in Trouble is actually about what’s going on with the women all around Toby.

Fleishman Is in Trouble turns the divorce novel plot on its head

Early on, Fleishman Is In Trouble reads like a standard contemporary divorce novel, albeit a witty and nicely written one. Yes, Toby is having lots of mildly kinky sex — mostly with women his own age, because younger women depress him — and he does indeed consider his ex-wife Rachel to be a crazy boner-killing shrew who won’t even mother their children properly.

“That was the big difference between them, Rachel,” Toby thinks in close third-person narration. “He didn’t see their children as a burden, Rachel. He didn’t see them as endless pits of need, Rachel. He liked them, Rachel.”

But hidden on the bottom of the first page, there’s a hint that something different is going on in this book. While we have full access to Toby’s thoughts through that close third perspective, Toby’s not our narrator. Someone else is, and she slips herself unobtrusively into the end of the opening paragraph about all the women Toby gets to sleep with now that he is getting divorced: “Women who would fuck you like they owed you money, was how our friend Seth put it.”

The narrator is Toby’s friend Libby, and she deflects attention from herself with a devotion that feels almost pathological. She doesn’t even use the word “I” to introduce herself, just that unobtrusive “our,” a hint of first-person plural making its way into this stream of third-person thoughts. Over time, Libby gradually asserts more and more control over the story she’s telling, the story that Toby believes belongs to him.

Libby, like Brodesser-Akner, is a journalist who used to write profiles at a men’s magazine. (Brodesser-Akner wrote for GQ until 2017, when she became a full-time staff writer for the New York Times.) But while Brodesser-Akner is celebrated for her profiles of both men and women, Libby doesn’t like to write about women.

When she profiles a woman, Libby says, the story becomes all about the external barriers women face, the sexism and the discrimination, and after a while, she gets bored telling that story over and over again. But when she profiles a man, those barriers fall away. That means she can just write about “the true stuff of their souls — of all our souls — the wound lying beneath all the survivalism and circumstance.” Which means that it’s only in her profiles of men that Libby can really write about herself.

“That was what I knew for sure,” Libby says, “that this was the only way to get someone to listen to a woman — to tell her story through a man; Trojan horse yourself into a man, and people would give a shit about you.”

And so Libby, who is feeling dissatisfied in her marriage and stuck in her career, tells us the story of deeply aggrieved Toby Fleishman, who feels that his wife has abandoned him and his boss has ignored him.

But try as Libby might, she can never quite bring herself to ignore the woman lurking behind Toby’s story: Rachel, that archetypal shrewish wife who just does not understand Toby and everything he has done for her. The more we hear Toby’s account of all of Rachel’s sins, the harder it becomes to ignore the idea that perhaps Toby is the one who is not understanding something basic and fundamental, that perhaps the heart of the story — the most important thing here — has nothing to do with him at all.

That’s the Taffy Brodesser-Akner trick, the thing that makes her profiles so clear-eyed and important, the thing that lifts her divorce novel head and shoulders above so many others in its genre: She is always willing to extend her empathy to people we are trained to believe are not worthy of our consideration. She is always willing to treat them as real people.

So in the end, perhaps the Fleishman who is in trouble isn’t Toby at all. Maybe it’s Rachel.

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