“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…”
- Taffy Brodesser-Akner, Fleishman Is in Trouble: A Novel
Taffy Brodesser-Akner’s Fleishman Is in Trouble giddily embraces so many topics that it’s hard to say what it’s about. It starts as a humorous look at a fortyish man who has just exited his marriage and entered the world of online dating apps. Then it starts to morph into the deconstruction of that relationship, with a close examination of the shifting power dynamics and inverted gender roles in modern heterosexual relationships. Along the way, it has plenty of things to say about parenthood, careers, social media, and overarching systems. Many of those things are incisive and beautifully worded, for this is a novel that overflows with talent.
It also creates a thematic mess that frequently contradicts itself as its many threads cross and recross.
More importantly, at least for me, is the fact that it centers on an emotional war to the knife between two privileged, entitled, wholly unlikable people, a war fought in a fairyland New York City where everyone has a doorman. I didn’t care at all about either of the dual protagonists, and thus, didn’t care for the book they’re asked to carry.
***
Fleishman Is in Trouble operates along three different paths.
The present-day focuses on Toby Fleishman, a liver-specialist in the Big Apple who is the first man in recorded history to get divorced. At least, that’s how he acts. Having left his thirties behind, the now-single father of two decides to get into the 21st century romance game. Using a dating app called Hr – one of Brodesser-Akner’s many gleeful inventions – Toby embarks on a sexual bacchanalia of the kind he could only have imagined in college. Each day, each hour, he is bombarded with explicit photographs that are listed with precision, as are his eventual conquests.
But then, just as he is about to fully engage with this carnal buffet, Toby’s ex-wife Rachel drops off his kids early one morning and disappears. A normal human operating with a semblance of concern would be worried about this turn of events. Not Toby. He is instantly, almost frighteningly mad, upset that he has been left as a single parent while there are sentient beings willing to consent to intimate relations only a couple of bus stops away.
While Toby attempts to navigate caring for two children with only a doctor’s salary and thousands in child support – he eventually sends them to a fancy summer camp – the story begins to circle back to scenes from his marriage. These flashbacks constitute the bulk of Fleishman Is in Trouble, and the picture Toby paints of Rachel, and their relationship, is downright terrifying. Rachel is described as a monster, better suited to eating bones beneath a bridge than running a successful talent agency, a career that Toby bitterly resents.
A major subplot – the third pathway I mentioned above – comes from our first-person narrator, Libby, who is a college-friend of Toby’s. She has her own hill to climb, meaning that she lives in the inner circle of hell (the suburbs), and is curiously frustrated by contentment.
***
Since I mentioned Libby, it’s worth briefly visiting Fleishman Is in Trouble’s structure. Though Libby introduces herself by the end of the opening paragraph, much of the story is presented strictly from Toby’s point-of-view, including thoughts only he could know. There is some implication that Libby could have learned everything from Toby at some point, but that’s not really possible at this level of detail. For long stretches, this feels like it’s written in the third-person.
What makes this interesting is that Toby – as Brodesser-Akner has admitted – is a transplant from an Updike novel, a man of a certain age who has never received the level of sexual gratification to which he believes he’s entitled. The twist is that this really isn’t Toby’s story at all, but Rachel’s, and is being told by a woman. Libby explicitly states the reason for this convoluted setup: “the only way to get someone to listen to a woman [is] to tell her story through a man.” Whether this conceit works will probably consume most of your book club.
Initially, I liked it, with the early-going funny, well-paced, and filled with snappy lines.
Then Libby interrupts the Toby-Rachel storyline to insert herself forcefully into the proceedings, bemoaning her very existence. Specifically, she wants to tell us about the Plight of the Upper Middle Class.™
What is the Plight of the Upper Middle Class? Why, it is the intellectual crisis that one is able to indulge after all basic human needs have been met: food, clothing, shelter, primary education (private), medical care, secondary education (private), second shelter (Vail or the Vineyard), post-secondary education (Yale, with Columbia as a fallback), and a country club membership. Libby is married to a rich lawyer, has two healthy kids, a nice house, and no economic worries, so everything she complains about – and it’s a lot – falls into the category of upper-order actualization far beyond anything anticipated by Maslow.
***
The unacknowledged gift of limitless disposable income warps everything Brodesser-Akner is trying to say. I’ve considered whether this is a satire of affluent New Yorkers, but it’s not. Brodesser-Akner approaches the class anxieties of her characters with utter seriousness, asking us to care – I mean, really care – whether Rachel Fleishman can make the leap from merely rich to generationally wealthy. Around the third time that she reminds us that Toby’s $300,000 salary is “good” but not “great,” it’s pretty clear she means it.
I bring this up because drama requires stakes. The higher the stakes, the better the drama. There are no stakes here. Toby is well-off. Rachel is well-off. The divorce isn’t going to ruin them, as it could possibly ruin someone who isn’t perched atop the highest marginal tax rate.
Meanwhile, Libby is burdened with a final act monologue in which she explains what you were supposed to have learned in the preceding pages. With the muddle of interlocking motifs, it’s not surprising that Brodesser-Akner decided to go this route. Moreover, everything that’s said – regarding gender inequalities, female relegation, and the cap on ambition caused by motherhood – rests on widely-experienced truths. For me, though, that message is obscured by the messenger. Libby has eluded those roadblocks with help from a platinum card. She isn’t engaged in the impossible balancing of – for instance – a single-mother keeping an hourly job while still picking her kids up from school. She’s a writer in self-imposed exile who can work from home and afford all the daycare she does or doesn’t want. This speech felt unearned, an act of appropriating the problems of others.
***
But that’s not even the deal-breaker.
It’s the characters.
Even though Toby’s viewpoint is the one most often expressed, I knew from the first ten pages that he was a raging asshole. This is a guy who doesn’t need to wear clothes, because he’s cloaked in his own self-righteousness. Sarcastic, moralistic, hypocritical. In one scene, he turns down a million dollar yearly salary without discussing it with Rachel, all because of his “principles.” Then he screams at her because he blames her for the offer. He’s borderline psychopathic.
Then there’s Rachel.
Initially presented as a one-dimensional villain, you are told early on – by the Table of Contents – that she’ll eventually get to tell her side of the story. Brodesser-Akner handles this really well, giving us mirror-twinned scenes that replay already-discussed events from Rachel’s perspective. There are also elements of her backstory that make her far more sympathetic, and I appreciate that. Nevertheless, a person’s history can explain their actions without excusing them. Ultimately, whatever Rachel went through, she ends up treating others like disposable rubbish, instead of people.
I’m not sure I bought Brodesser-Akner’s explanation for why Toby and Rachel ended up together in the first place, but by the time of their split, I was convinced they were meant for each other.
***
I’ll be the first to admit that Fleishman Is in Trouble is not my typical literary genre. This was a buddy-read with my wife, in preparation for the television show we planned to watch together. As you might have guessed, she is now watching that alone.
My experience with this novel is that alone: mine. It’s entirely subjective, and filtered through my own pet peeves, one of which is frivolous and moneyed individuals committing self-inflicted wounds in a whitewashed New York City. If you can get past that, then perhaps Brodesser-Akner’s ideas land with more impact.
Beyond that, I fully admit that Fleishman Is in Trouble engages you, it asks questions, it pokes at you, it’s meta-textual, commenting on itself as it goes along, demanding discussion. It is gorgeously written, though the prose is in service to a product that – in my opinion – it doesn’t deserve.
Clearly, this is a novel I disliked. But I really enjoyed disliking it, and will probably remember it far better than the next book I claim to love.