Contemporary

Review: Fleishman is in Trouble

Cover of the book, featuring a close shot of a section of New York City skyline, flipped upside down so that the sky is at the bottom of the cover and the lower floors of the buildings are at the top.

Title: Fleishman is in Trouble

Author: Taffy Brodesser-Akner

Genre: Contemporary

Trigger Warnings: Sexual content (a lot), divorce (major), infidelity, abandonment, fatphobia/body shaming/disordered eating/moralizing about food (frequently mentioned), mental illness, terminal illness (mentions; not protagonist), medical content (mentions; because protagonist is a doctor)

Back Cover:

A finely observed, timely exploration of marriage, divorce, and the bewildering dynamics of ambition from one of the most exciting writers working today.

Toby Fleishman thought he knew what to expect when he and his wife of almost fifteen years separated: weekends and every other holiday with the kids, some residual bitterness, the occasional moment of tension in their co-parenting negotiations. He could not have predicted that one day, in the middle of his summer of sexual emancipation, Rachel would just drop their two children off at his place and simply not return. He had been working so hard to find equilibrium in his single life. The winds of his optimism, long dormant, had finally begun to pick up. Now this.

As Toby tries to figure out where Rachel went, all while juggling his patients at the hospital, his never-ending parental duties, and his new app-assisted sexual popularity, his tidy narrative of the spurned husband with the too-ambitious wife is his sole consolation. But if Toby ever wants to truly understand what happened to Rachel and what happened to his marriage, he is going to have to consider that he might not have seen things all that clearly in the first place.

A searing, utterly unvarnished debut, Fleishman Is in Trouble is an insightful, unsettling, often hilarious exploration of a culture trying to navigate the fault lines of an institution that has proven to be worthy of our great wariness and our great hope.

Review:

I still occasionally talk about the AP English Literature class I took my freshman year of high school. As I wrote in 2022, “Every single novel I had to read for the class was about divorce, marital infidelity, or divorcing over marital infidelity. All of these novels were the ‘literary’ kind. And I hated every. single. book.”

Fleishman is in Trouble is a literary, largely plotless novel about a middle-aged man going through a divorce and having a lot of sex to try to deal with it. So I bring up this literature class yet again to emphasize how astonishing even I find it that not only did I pick up this book, and not only did I finish it, I actually enjoyed it. (Up until the end, which I’ll get to in a second.)

These characters and this world feel like the embodiment of a “live your best life,” “#girlboss,” “you can have it all” aesthetically-pleasing rich-girl Instagram account. You know the type. The primary characters in this book (a New York City doctor divorcing his millionaire publicist wife) are aggressively unrelatable to me (a secretary living on 75% of the national average salary in the Midwest). It has very little in terms of a plot. But the thing that this book does so well, and that made me eager to keep reading despite all these factors that should have made it feel exactly like the books I hated in AP Lit, is that it so perfectly captures the tensions of living your “best life” in the modern world. You’re already stretched to your breaking point but the mandate of self-actualization demands you do more. You hate these people and everything they stand for and yet you must also fit in and earn their respect, if not admiration. You’ve been dealing with burnout for so long that you can’t even recognize that’s what it is. You simultaneously feel that you’re doing the bare minimum and that you’re doing too much. You just want those closest to you to recognize – not even necessarily appreciate, just recognize – how much time and effort you’re putting into keeping so many different things running – for them! – but all they ever seem to notice is the things you don’t do.

I have a lot of feelings about modern life, how doing it “perfectly” requires multiple conflicting things to be true at the same time, and how keeping on top of everything you’re “supposed” to do won’t result in a feeling of accomplishment or peace but in constantly feeling stressed and behind. And this book puts those feelings into words better than I ever could. In fact, I think making the story about rich people living dramatic lives in New York City is actually a better choice than something more easily relatable. Big lives enable the problems to become bigger, more obvious, almost caricatured to make the point. And it works.

Toby and Rachel are both not great people for different reasons. They’re both victims but they’re both victims of their own decisions. Their multiple penthouses and multi-million-dollar deals set them a world away from most things relatable to the average reader. But if the question is relatability, I will always choose Rachel. Toby has his own struggles and his story isn’t bad. Rachel throughout the book is portrayed as a monster. And though she’s definitely not as terrible as Toby thinks, she’s not a good person. But despite possessing wealth that I can only dream of, despite having the type of high-powered job that I neither want nor am likely to get, she was still relatable. She was relatable in being a person doing too much in a world that always demands more, and in being a woman and primary breadwinner in a heterosexual relationship that is unequal not due to any particular malice on the part of her male partner, but because the system of heterosexual relationships is inherently unequal and he has never bothered to consider how he might be passively benefitting at her expense.

The other thing that this book does wonderfully, but more subtly, was explore both sides of this kind of relational destruction. Even through the filter of Toby’s hurt and rage, I could still easily understand Rachel’s thought process and emotional state. But with Toby as the protagonist, I also saw his thought process. It was, above all, a failure to communicate on both sides. But it did do an interesting job of illustrating how even though it can feel like this person is just overtly refusing to meet your needs, chances are they also feel like you’re refusing to meet their needs. (Although the communication scholar in me wants to yell at them that if they were better about communicating what it actually was they needed they could avoid a lot of problems.)

The final thing I want to touch on as I start bringing what could be a really long review into some sort of ending is not so much something the book does or accomplishes, but a major theme that it touches on. And that is the theme of how relationships threaten female identity. A single woman, unattached, can be herself. A married woman must remove some of herself to make room for her new identity of wife. A mother must remove even more to take on the new identity of mother. Both of these other identities, taken on not because the woman chose to but because of her ties to someone else, have the potential to grow and push out even more of an individual identity – motherhood especially, until there is no more I, only Mother. I did not expect a book largely focusing on the man’s side to come out in such support of the woman, and women everywhere. It’s a deep, subtle exploration that may not even be recognized for people who don’t relate but will be blatant and resonant for anyone who is or has experienced similar feelings.

I went through most of this book ready and eager to write a glowing review (in case you can’t tell from the fact that my review so far has been so positive). There were a couple points where I actually had to stop myself from starting the review before I finished it because I was so eager to share how good this book was. And there’s a reason for that, and that reason played out especially true for this book. That reason is sometimes the ending doesn’t live up to the rest of the book. And when I say “ending” here, I’m mainly talking about the last few pages. The whole long, rambling story up to that point subtly and masterfully explored unique ideas and interesting themes – I hesitate to say “the human condition” because that’s very broad and also somewhat pretentious, but perhaps “the modern human condition” is fitting. And then in the last few pages, this previously rich and subtle book starts jumping up and down waving its arms in the air and shouting, “Hey! Here’s all the themes we’ve been talking about for the past 400 pages! Pretty neat, huh? Here’s an easy and quick answer to these big questions!” It felt jarring and discordant with the rest of the book, like the author didn’t quite know how to end it but wasn’t comfortable leaving the readers with no answers. It also felt cheap and almost dismissive, as if nothing it touches on actually matters because there’s a quick answer. Though it didn’t technically ruin my experience of reading the rest of the book, it thoroughly dampened my enthusiasm.

Sometimes books just come to you at the right time. I can guarantee that if I’d have picked this up even a few years ago, I probably would have found it dull and unlikeable. In fact, a few years ago I probably wouldn’t have picked it up at all. But I think I’m at the point in my life where I can appreciate the thematic resonance of a book about divorce featuring generally unlikeable characters. Despite my feelings about the ending, I still appreciate what the rest of the book had to say. It was definitely a different reading experience than my usual fare, but sometimes looking somewhere new leads to a surprise gem. And this is a book worth reading.