'Fleishman Is in Trouble' by Taffy Brodesser-Akner

Review #111

Taffy, my friend, has done it! Her debut novel is a hit! Oprah’s recommending it. It’s been a New York Times bestseller. Candace Bushnell and practically everyone I know has read or is reading ‘Fleishman Is in Trouble’:

Taffy didn’t ask me to do this review, even though she has supported Books on GIF from the very beginning. To be honest, I didn’t think I would review it when I bought a copy at her book launch party earlier this summer. At the time, I was more focused on the hammock suspended from the ceiling in that loft. That was nuts! Her protagonist, Toby Fleishman, would have loved to have sex on that thing. I just wanted to sit on it, but it would be just my luck that it would collapse under me and all the assembled luminaries of the book and media world would laugh and laugh. Anyway, after the party when I was sitting with Donna at the bar in Old Town trying to take the perfect Instagram post of the book lined up next to my bourbon, I figured no way was I going to do a review. Sure, I reviewed Jen Doll’s book earlier this year, but if I did a newsletter about all the books written by people I know, I’d have to rename this newsletter Books on GIF & Friends. Besides, our friendship is too important to me. I couldn’t take it if there were irreconcilable differences between us. No, it was too dangerous. I couldn’t risk it. But the next night, I went to Taffy’s event at Books Are Magic. I heard her talk about her book, how it was about divorce, how people she knew wondered whether the characters were based on them and how she welcomed criticism. Standing in the back of the bookstore, it hit me. Of course I was going to review this book. How could I avoid it? I don’t have time for reading things that don’t eventually end up here. Plus, this is the book of the summer! But if I’m still being honest, I’ve struggled with this decision. Not because I didn’t like Taffy’s book. I liked it quite a bit. That’s been the problem. Where to begin? What to say? Writing this review has stressed me out completely. I blew a deadline two Sundays ago, and I almost never do that. Seriously, for two weeks I have sat at my computer like:

But then I remembered that night at Books Are Magic. I remembered that she took a big risk in doing a novel. She could have just kept cranking out those incredible profiles of celebrities for The New York Times. But she pushed herself into a whole new world of writing, and pulled it off. I was inspired. I said to myself:

And here we are. For those of you who haven’t read Taffy’s book, it tells the story of Toby and Rachel Fleishman, an Upper East Side couple in the throes of a divorce. Toby is a doctor specializing in liver ailments. Rachel heads her own talent agency and has famous clients. One morning, Rachel drops off their two children at Toby’s new apartment on her way to a retreat at Kripalu. She never comes back. Toby is concerned about Rachel’s disappearance only insofar as her absence means he has to watch the kids longer than expected, thus inconveniencing his hospital work, and also his sexting and late night assignations with female strangers. He assumes his soon-to-be ex-wife is off working and forgot about her children, or is simply punishing him. He tries to push through his mounting troubles at home and at work like:

All of the characters in what to me is a satirical book are unlikeable, and I don’t think you’re supposed to like them. Instead, they are meant to hold up a mirror to the vanity, banality and emptiness of late capitalism’s white bourgeoisie. The worst of them is Toby, a man perceptive enough to diagnose a rare liver disease, but blind to his narcissism and its destructive power. There is so much to despise about him, like how he would explode at Rachel and once threw a piece of chicken at her in front of their kids, how he packed his children off to camp so he could focus on sexting, how he dismissed the nanny and how he did next to nothing to find Rachel. I hated him so much that I hoped he would be murdered by one of his sexting partners. Even so, Toby is an interesting character as a story-telling device. The more his character is colored in, the more we also see Rachel in the negative space. Without spoiling the book, I thought the section that unravels the mystery of Rachel’s disappearance was the most interesting part and featured some of its best writing. We learn she wants to be loved and affirmed after being raised by a cold grandmother. She has been unable to establish a healthy work-life balance, and doesn’t find love and support at home, at work or in other relationships. Life has come at Rachel fast, like:

She thought she would have these needs fulfilled by Toby. But time and again she is ignored and misunderstood for who she is, and is punished for who she is not. When she realizes that she is totally alone, she sinks:

My main gripe with the book is the narrator, Toby’s female friend. The story seems to shift back and forth from the third person to this character’s first person account, and that was jarring. But she does offer what to me feel like meta explanations of Taffy’s choices for the story. For example, as I mentioned earlier, I thought Taffy was telling the story of a woman through the actions of a man. On page 236, the character, a former writer for men’s magazines, says: ‘That was what I knew for sure, 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.’ This character also offers an explanation about unlikable characters and tips us off to the book’s ending. But whenever this character took over the storytelling, I was like:

Taffy’s book is a grenade lobbed at Generation X, challenging our conceptions of marriage, how we treat women and how we view ourselves. The characters feel real, and they tell a story about how anger, resentment and miscommunication tear us apart. About how our wives are bound by oppressive expectations. About how our society punishes them for too much success, for being vocal, for getting pregnant, for not getting pregnant, for getting old, for gaining weight or for wanting to be more than someone’s sexual object. About how our husbands are not equipped to understand or to help. About how we cannot forgive our spouses if they fail to live up to our expectations or ambitions. About how collectively our generation lacks purpose, meaning and empathy. Remember back in the day when we all vowed to stay true and never sell out? Now our truth has been reduced to ‘Live, Laugh, Love’ slogans splayed across our athleisure, as worn by some characters in the book. (I couldn’t help but think of the instructor the time Taffy and I did ‘Hamilton’ SoulCycle who chastised me for wearing sweatpants while he wore Star-Spangled Banner leggings.) I was reminded of this scene from ‘Fight Club’:

It’s all so depressing, and I don’t know where we go from here. Taffy’s goal doesn’t seem to be to fix marriage or society, but to show their true forms, warts and all. She tells a very human story that provokes introspection. At least for me. I haven’t stopped thinking about it for two weeks. I liked this novel and I hope Taffy writes another, like the one where the moms form a street gang.

How it begins:

Toby Fleishman awoke one morning inside the city he’d lived in all his adult life and which was suddenly somehow now crawling with women who wanted him. Not just any women, but women who were self-actualized and independent and knew what they wanted. Women who weren’t needy or insecure or self-doubting, like the long-ago prospects of his long-gone youth—meaning the women he had thought of as prospects but who had never given him even a first glance. No, these were women who were motivated and available and interesting and interested and exciting and excited. These were women who would not so much wait for you to call them one or two or three socially acceptable days after you met them as much as send you pictures of their genitals the day before. Women who were open-minded and up for anything and vocal about their desires and needs and who used phrases like ‘put my cards on the table’ and ‘no strings attached’ and ‘I need to be done in ten because I have to pick up Bella from ballet.’ Women who would fuck you like they owed you money, was how our friend Seth put it.

Yes, who could have predicted that Toby Fleishman, at the age of forty-one, would find that his phone was aglow from sunup to sundown (in the night the glow was extra bright) with texts that contained G-string and ass cleavage and underboob and sideboob and just straight-up boob and all the parts of a woman he never dared dream he would encounter in a person who was three-dimensional—meaning literally three-dimensional, as in a person who wasn’t on a page or a computer screen. All this, after a youth full of romantic rejection! All this, after putting a lifetime bet on one woman! Who could have predicted this? Who could have predicted that there was so much life in him yet?

Still, he told me, it was jarring. Rachel was gone now, and her goneness was so incongruous to what had been his plan. It wasn’t that he still wanted her—he absolutely did not want her. He absolutely did not wish she were still with him. It was that he had spent so long waiting out the fumes of the marriage and busying himself with the paperwork necessary to extricate himself from it—telling the kids, moving out, telling his colleagues—that he had not considered what life might be like on the other side of it. He understood divorce in a macro way, of course. But he had not yet adjusted to it in a micro way, in the other-side-of-the-bed-being-empty way, in the nobody-to-tell-you-were-running-late way, in the you-belong-to-no-one way. How long was it before he could look at the pictures of women on his phone—pictures the women sent him eagerly and of their own volition—straight on, instead of out of the corner of his eye? Okay, sooner than he thought but not immediately. Certainly not immediately.

My rating:

‘Fleishman Is in Trouble’ by Taffy Brodesser-Akner was published by Random House in 2019. 373 pages. $27.

Four for the road: More things worth your time.

  • Read this: ‘The Crane Wife’ in The Paris Review is practically a companion piece to ‘Fleishman Is in Trouble.’

  • Follow this: Boss Betty is a new business site ‘focused on gender equality in the workplace,’ started by my friend Heather. Subscribe here. Sign up for the newsletter here.

  • Do this: Bassey Ikpi, a Nigerian-born spoken-word poet and mental health advocate, talks about her new essay collection, ‘I’m Telling the Truth, But I’m Lying’ with Melissa Febos at Books Are Magic on Weds., 8/21. More information here.

  • Remember this: I’ve forgotten who recommended this Wesley Morris eulogy for Toni Morrison, but thank you. It is beautiful.

In two weeks you’ll get a review of ‘Disoriental’ by Négar Djavadi. Also in the queue are ‘My Year of Rest and Relaxation’ by Ottessa Moshfegh, ‘The Great Believers’ by Rebecca Makkai and ‘Kudos’ by Rachel Cusk, among others. 

In case you missed it: Books on GIF #110 featured ‘Sing, Unburied, Sing’ by Jesmyn Ward.

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Thanks for reading, and thanks especially to Donna for editing this review!

Until next time,


With GIFs from @maremonstrum @xavieralopez @ethanbarnowsky