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Decoding the book of the summer, Fleishman Is in Trouble

Our panel debates Taffy Brodesser-Akner’s debut novel, from dating apps to Presidentrix.

Fleishman Is in Trouble, a book by Taffy Brodesser-Akner. Random House

Critics have anointed Taffy Brodesser-Akner’s debut novel, Fleishman Is in Trouble, the book of the summer.

Fleishman Is in Trouble is a New York Times best-seller. It’s received raves from reviewers at the New York Times, the Washington Post, NPR, and the New Yorker, among others (including Vox!). The book review aggregator Bookmarks can’t find a single negative review of it, and only one that’s so much as mixed. Fleishman seems to be one of those books that everyone agrees has universal things to say about the human condition, and is warm and funny to boot.

It deals with Toby Fleishman, 41, newly separated from his wife and entranced by the dating apps that now populate his phone. But as Toby revels in his new freedom, he slowly realizes that his soon-to-be-ex-wife, Rachel, isn’t just absent from his life. She seems to have fully disappeared.

Here at Vox, we decided to take a closer look at what all the fuss was about. Vox book critic Constance Grady sat down with deputy policy editor Libby Nelson, engagement editor Nisha Chittal, copy editor Tim Williams, and Today, Explained intern Will Reid for a roundtable discussion. Together, we talked Fleishman, the state of the marriage novel, and that ambiguous ending. If you haven’t read the book yet yourself, beware of spoilers below.

Fleishman is a smash hit. But is it fun to read?

Constance Grady: Fleishman Is in Trouble clearly wants to be a big, ambitious novel that has things to say about gender and marriage and class and living in America today, and we’ll get into how it handles most of those in a little bit. But just to start off, let’s hit the most important question of all: Is it enjoyable to read?

For me: Yes, very much so! If you’ve read one of the profiles that Taffy Brodesser-Akner has written in her other life as a magazine writer, you know that she can really write a sentence, so it’s not a surprise that her prose is sparkling and twisty and witty all the way through the novel. But what really impressed me about this book is actually the same thing that I think elevates Brodesser-Akner’s profiles above basically every other writer’s in the game: She always goes out of her way to find the humanity in her subjects, even the ones that she knows her readers are looking forward to mocking.

In another writer’s hands, that Gwyneth Paltrow profile just becomes a collection of wacky things Gwyneth says that can get aggregated into a snarky listicle, right? And in another writer’s hands, Toby really is the aggrieved and wronged party that he believes himself to be and Rachel really is the bitter shrew that he presents her to us as.

But with Brodesser-Akner at the helm, it’s impossible not to empathize with everyone, even when we can very clearly see their failings and their foibles. For me, that’s what makes this book so absorbing to read.

But that’s just me! Did it work for you? Or are you a Fleishman skeptic?

Libby Nelson: I am a gulper-down of novels in general, and I read the last half of Fleishman in a propulsive sprint, finishing it on my couch at 2 am on a workday. But this speed-read astonished even me, because it should have been so not my thing: I can appreciate good contemporary literature with a well-turned sentence, but the books I love and read late into the night are usually plot-driven novels, often set in the past or with murders or both, with women as their primary protagonists. If I weren’t a Taffy Brodesser-Akner completist who viewed preordering her first novel as something akin to an obligation, I likely never would have picked it up at all.

I’m so glad I did, because if I hadn’t, I would have missed out on Presidentrix, a running bit through Brodesser-Akner’s book. One of the characters is an agent who represents the creator of Presidentrix, essentially a through-the-looking-glass, gender-flipped version of Hamilton: an unlikely biography-as-musical by a Hispanic artist about Edith Wilson, Woodrow Wilson’s wife. I volunteered for this discussion mostly so I could yell about Presidentrix, because it deserves more credit for being both one of the funniest things I’ve encountered in a book in ages and a neat encapsulation of some of the broader points Fleishman Is in Trouble wants to make about gender and narrative.

So yes, I enjoyed it — somewhat to my surprise. Not all of it worked perfectly for me, for reasons I’m sure we’ll explore, but Brodesser-Akner’s voice and wit were more than enough to carry me through.

Nisha Chittal: This book is extremely my cup of tea — I love contemporary novels about adults navigating the messiness of modern life — and it did not disappoint. Many reviews have described this as a book about marriage or a book about a divorce, but I also saw it as about something broader: middle-age malaise. Everyone in Fleishman Is in Trouble, whether it’s the Fleishmans or their friends or the narrator, appears to be having a midlife crisis of some sort. (After finishing the book, I immediately started worrying about whether this is just what being in your 40s looks like.)

What I found most surprising about the book is how Brodesser-Akner tricks readers into sympathizing with Toby Fleishman. The story is told from his perspective for the vast majority of the novel, and Rachel is unquestionably the villain in the marriage — she’s a cold, careerist social climber who’s never home from work early enough for dinner with the kids, while Toby is a martyr who singularly does all the child care.

There are, of course, two sides to every story, and a savvy reader will probably pick up quickly that something is missing in Toby’s story. When you finally hear Rachel’s side of things at the end of the book, it delivers an immense payoff for the reader, and I think it will particularly resonate with a lot of female readers. I loved that the ending really underscored the invisible work that women often do, the immense amount of pressure they face, and how little the men in their lives understand both of those things.

Will Reid: Nisha, I love what you said about feeling sympathy for Toby. How could we not when we feel we understand his perspective so well? But I’m sure I wasn’t alone in the dread of feeling we weren’t getting the whole story. At times, the book honestly felt like a horror movie: I found myself constantly trying to anticipate when a jump cut would reveal the monster Toby really was.

That’s not, in the end, entirely how things turned out. (Rachel treats Toby with far more empathy than he extends to her, and so I found him less monstrous than pathetic.) But the suspense kept me reading well past my bedtime. I was happy to give up the sleep.

Another thing I enjoyed: Brodesser-Akner’s narrator. Elizabeth Slater, née Epstein — who goes by Libby — is an old friend of Toby’s from college. They’ve fallen out of touch until the divorce drives Toby to call her for support. (We eventually learn that she’s spending hours and hours on the phone with him, her own escape from middle-age malaise.)

Biographically, Libby’s too much like the author not to notice: Like Brodesser-Akner, she’s a writer who lives in New Jersey and who used to work for a men’s magazine writing celebrity profiles. (Brodesser-Akner wrote for GQ.) So what you pointed out, Constance, about bringing the same sensitivity to contradiction and humanity to bear on her fictional characters as she does her profile subjects doesn’t feel like an accident. It’s baked into the character.

What I really like about Brodesser-Akner’s nonfiction is the way she plays with pulling back the curtain. Her profile of Bradley Cooper, for instance, is as much about the actor as it is an argument in favor of the celebrity profile itself. So it didn’t surprise me when, in a magnificently meta moment, Libby proposes to write the book we now hold in our hands and tells Toby (and us) how it ends. To use a sports metaphor Toby would abhor, Brodesser-Akner tees up the ending for herself and drives it to a satisfying finish.

Libby: When it comes to the broader arguments the book wants to make about gender, narrative, and whose stories get listened to, planting the way that Libby weaved her own life experience into the profiles she wrote of famous men is brilliant. (This brings me back to Presidentrix again: It’s a very funny joke, but the humor works in part because society views women’s stories as worth less than men’s. A buzzy modern musical about a forgotten Founding Father is improbable — try to remember how bizarre “hip-hop musical about Alexander Hamilton” sounded when you first heard it — but the suggestion of a similar show about a woman, no matter how fascinating her forgotten story is, cranks up that unlikeliness to pure satire.)

From a narrative and character perspective, the same tricks that make Fleishman such a compelling and vital book occasionally made the story not quite land for me. Are we supposed to assume that Libby’s narration is reliable, or read Toby’s experiences as a blend of his own and his narrator’s? What, in the end, are we supposed to make of Rachel, and Toby, and their marriage? The final pages depicting Rachel’s insomnia and breakdown are harrowing — I’m not sure I’ll ever look at Chinese takeout the same way again — but I couldn’t help but wish that we’d had a bit more of her, that her narrative had been given a few minutes to breathe.

Tim Williams: I found this book engrossing, but I did have some nitpicks: I don’t think all the characters get the full empathetic profile treatment Brodesser-Akner is known for. The main ones, certainly! It’s an inspired choice to make Toby the self-proclaimed “good parent” who actually does seem like a good parent in many ways. Rachel is a never-satisfied multimillionaire, but we come to understand why, and root for her too.

But the characterization and dialogue of others (for me, this includes finance bro Seth and some people in T-shirts with embarrassing slogans) occasionally feels over-the-top or too neat. Brodesser-Akner deploys the repeated use of “I don’t know” in one memorable line from young resident Joanie: “I thought I don’t know. I know you just got divorced and I know it’s not the same thing but I’m sad and you’re sad and I don’t know.” I liked it, but it might arguably take away from the poignancy beneath her words.

Many of the stylistic choices I really liked, though. The dating app hellscape is a huge part of the book; it could easily come off as immediately dated, but it just works. That recurring waking nightmare about Chinese takeout food is a standout in the impeccable section where we finally get to meet Rachel and the horror brought upon her.

The marriage at the center of Fleishman Is in Trouble is toxic to the core

Constance: Another big question: Is this book’s treatment of marriage and the way marriage and gender interact convincing?

I am not married, but what impressed me about the treatment of marriage here was that no one person’s understanding of it is completely allowed to dominate the book. Toby has all these righteous idealistic ideas about marriage that are curdled by his own resentment, but you also have Seth, who feels empty without marriage, and Libby, who is very clear-eyed about how much she likes being married, even when she feels trapped by it.

Libby has that great line toward the end: “What were you going to do? Were you not going to get married when your husband was the person who understood you and loved you and rooted for you forever, no matter what?” There’s this sense in her narration that being married will involve long periods of discontent and frustration but that it’s still worthwhile, which is actually pretty optimistic for a divorce novel.

But the central marriage in this book revolves around one major concern: Is it possible in our culture, given its gender norms, for a woman to outstrip her husband in ambition and wealth and career and for everyone involved to be okay with it? Or is that woman always going to be trapped under the weight of everyone else’s expectations?

The Fleishman marriage would seem to argue that maybe she can’t. And Libby’s marriage isn’t necessarily a very optimistic answer to that question either, because Libby leaves her job as a journalist in part because she can’t deal with the pressure of having to be a mom while also working a full-time job. But there’s also a suggestion that she maybe writes Fleishman Is in Trouble, in which case I guess she’s a celebrated New York Times best-selling author now, so maybe it works out for her.

For me, the conclusions Brodesser-Akner seems to come to on these questions — that a marriage in which the woman is the primary breadwinner can maybe work, but not without a struggle, or without both partners trying — feel convincing. But does it work for you?

Nisha: The book really emphasizes the idea that gender roles are reversed in the Fleishman marriage; a lawyer even once tells Toby that he’s “the wife.” Rachel is the workaholic and the breadwinner, while Toby cooks and takes care of the kids (he’s no slouch, as a doctor, but he doesn’t aspire to climb the ladder much higher). And Brodesser-Akner masterfully illustrates how tough it is for women to pull off this arrangement, even in the supposedly woke era of 2019.

Although Rachel started her own business and makes a seven-figure income that supports the entire family, Toby still resents her for not spending as much time with the kids as he does, and for extending her business trips by an extra day. These are things that would be pretty common for a male partner in a heterosexual marriage — but when a woman does it, she’s viewed by those around her as too ambitious, too careerist, not family-oriented enough. And in the end, Rachel does break down because of the pressures to be and do everything and to fulfill the expectations of the men around her, pressures that she manages well for years but eventually can no longer cope with.

On the book’s portrayal of marriage: I think the Fleishman marriage is a particularly acrimonious one. They both harbor contempt and resentment toward each other. They both bottle up their feelings instead of talking about them. They have communication issues and seem to be on different pages about what kind of life they want. And Toby has a lot of insecurities that often manifest in resentment toward Rachel for being more ambitious than he is — both in her career and in the type of life that she wants. So it’s a portrait of a pretty toxic marriage, for sure, but I don’t take it as an indictment of marriage or even of whether an unconventional female-breadwinner marriage can survive. I just think that Toby and Rachel were phenomenally mismatched for each other, and that Toby perhaps has a lot to learn about all of the invisible work that women do.

I think Libby’s marriage to Adam is probably a more realistic portrayal of a happier marriage, even though Libby often chafes at the dullness of suburban New Jersey, and even though she eventually quit her men’s magazine job after feeling marginalized for years. To me, the overall message is that marriage is complicated, it takes work, and it isn’t what the rom-coms and Disney fairy tales lead you to believe. But that’s what I love so much about this type of book — it really captures the complexities of the human experience, and in that sense, it felt very convincing to me.

That said, I don’t think “complicated” and “it takes work” are bad things — they’re just accurately reflecting real life. Of course merging two lives legally and financially and logistically for life is complicated! That doesn’t mean it’s not worth doing. I think Brodesser-Akner’s overall message is a positive one: A healthy marriage where the partners both try, and are both the right fit for each other, can be a wonderful thing. All marriages have ups and downs, but the point is to have the ups far outnumber the downs.

Tim: I also thought the marriage crises — and one of the potential solutions — were specific and convincing. They build over time and a million tiny slights that each person can’t help but indulge in. Which is not to say the warfare is symmetrical; Rachel and Libby spend a lot of time anticipating how they will be misunderstood. Rachel finds it hard just to admit she hates long walks, let alone that she may have been sexually assaulted by a doctor.

In Libby’s magazine profiles, she can’t escape telling women’s stories as “the struggle to be the kind of woman who gets interviewed.” But even this kind of narrative confuses Toby, who doesn’t see Rachel’s boss hitting on her or retaliation for her becoming pregnant as systemic abuses of women in the workplace. Toby is only interested in his own narrative — and so he’s just mad that someone went after “his” wife.

So can these marriages work? Yes, but only if the people in them are willing to hear each other, and push back against the power imbalances that shape their stories. That’s really hard to do.

Brodesser-Akner finds this insight despite her book involving a small set of rich people, mostly on the Upper East Side of New York. The limits of this vantage point are carefully acknowledged: Toby is shown to despise any display of wealth besides his own, and Rachel’s struggles against workplace sexism are complicated by her occasionally exploitative treatment of the women below her. Still, I often found myself nodding along at the Fleishmans’ conflicts over tiny differences of class: what house in the Hamptons to buy and what cookware you are allowed to put in it. This bubble was both totally foreign and understandable.

The characters’ heterosexual bubble in the city was less convincing. I almost forgot that we do see a glimpse outside it. Rachel goes to the apartment of Presidentrix creator Alejandra Lopez in desperation, walking in unannounced for the first time in their long business relationship, and encounters Lopez’s wife, Sofia, a WASP stay-at-home mom.

The implications there are interesting. Did Sofia really want to quit her job? Are these two people replicating the power imbalances of other well-to-do couples, or are they totally at peace? But I wish we had heard a little more from voices like these; the discussions of marriage would feel more complete. Seth sort of serves as the marriage gadfly, but even with his cartoonish levels of privilege, he feels acute pressure to be included in respectable coupledom. (Which, same.)

Will: Tim, I hear your point. The novel concerns a rarified group with fairly narrow ideas about marriage. I’m someone for whom marriage is still a long way off, so I feel a bit out of place answering this question. But if the main takeaway here is that relationships take work, I sort of feel like ... duh? That feels enough like common knowledge among my own group of 20-somethings that it’s become cliché. (That having an SO is like taking an extra class was frequently memeified in our university-wide Facebook group.)

Where Brodesser-Akner’s novel feels new, and even a little radical, is that it asks whether happiness in marriage is possible at all. We don’t get a neat resolution here. Vanessa and Seth ominously get into an argument at their engagement party. Libby has to resign a lot about herself to feel happy in her marriage. (That she supposedly goes on to write the novel in an auspicious return to the writing life doesn’t feel like a convincing out, if only because we don’t know how that endeavor influences their marriage. Who knows? Maybe she and Adam don’t last.) And Rachel’s return might lead her and Toby to get back together and figure out how not to hate each other. Or it might not.

The characters do realize they need to accept themselves and their marriages, or lack thereof. Toby recognizes he might “figure out a way to extract himself from the idea that he lived in contrast to [Rachel.]” Libby thinks, “What would be so wrong with finally mellowing out?” We could call these realizations solutions to the problem. But the novel doesn’t put these solutions to the test. Instead, we’re left with a lot of ambiguity.

Libby: It’s hard to finish the last section and not want to immediately turn back to the beginning and see the whole story with new eyes. Fleishman Is in Trouble is a book that’s unquestionably of our moment — but also one that is seemingly built to reward rereading.

The ending is purposely ambiguous, but that doesn’t mean we can’t fight about it anyway

Constance: I agree that this is a novel we’re going to see people reread a lot, and I think one of the big pleasures of rereading will be getting the chance to change your mind about that ambiguous ending and then fighting about it.

So! Lightning round-style: In the ending, do you think Rachel is going back to Toby for good, and if so, is that a good thing?

My answer is that yes, she is going back to him, and no, that’s not a good thing. Rachel and Toby will be exactly as miserable as they always have been, because Toby is never going to put in the work to empathize with her — while Rachel is too trapped by her beliefs about what happiness should look like for her to break away from their marriage for good.

What do you think?

Tim: I agree that they get back together, despite Toby being the worst. Maybe one of them eventually pulls the plug; I don’t see Toby giving up his apps. But as we’ve already seen with the kids involved (a whole other discussion to be had!), their parental guilt will make it doubly hard to end things. And the impossible choices will continue regardless.

Will: They might get back together, but it’s hard to imagine Toby getting over Rachel’s disappearance (or her sleeping with Sam Rothberg, for that matter.) His moment of epiphany at the end seems conditioned on forgetting that Rachel ever existed: “If he could imagine ... she’d just sort of ascended into the heavens and would remain a ghost that some people sometimes saw, he could proceed.” That’s hardly a model for marital bliss. Don’t do it, Rachel!

Nisha: Yes, I think Rachel showing up on Toby’s doorstep means they’ll get back together, but I agree with Constance that I don’t think that’s a good thing. I think Rachel and Toby are ultimately not the right partners for each other, and they might have a brief honeymoon phase because they’re happy to be reunited, but ultimately I think their relationship will be just as unhappy and as unhealthy as it was before. Also after everything Rachel went through in dealing with the expectations of men — Toby and Sam — maybe she would be better off taking some time to herself!

Libby: I’m going to be the outlier here; I’m not sure that they’re getting back together or if Rachel’s just reentering Toby’s life after her absence. But maybe that’s wishful thinking, because what we’ve seen over the entire book prior to that moment really suggests that their marriage is likely beyond repair. If she is coming back, then I agree with the rest of you: It’s a very bad idea.