Book Review: “Fleishman is in Trouble”

For a first novel, Taffy Brodesser-Akner’s Fleishman is in Trouble is incredibly observant about midlife crises and how dating has changed in the last couple of decades. The story centers on Toby Fleishman: a 41-year-old doctor who is a liver specialist working in Manhattan who is going through a divorce with two children to care for. That set up alone isn’t anything interesting, but we live in an interesting time to be single — especially if you’re in your 40s and 50s. Toby is not a Boomer or a Millennial, rather he was born in that generation that doesn’t get much attention in popular culture and social commentary — even though it’s a generation that came of age in and shaped the so-called contours of the digital age. I’m talking about Gen X — a group of adults in their late 30s to mid-50s. For those in that cluster, dating rituals through the decades run the gamut of simply asking someone out in person, to the proto-app period of dating websites, or the blunt sexual sewers of Craigslist. Like many fads, apps are the new black, and in Brodesser-Akner’s novel, the main character (Toby) is overwhelmed and excited by how easy it is to skip the wining and dining of yore and go straight to sex.

For a man who has been in a long term marriage with kids, suddenly being desired by women (and not just some, but many) does quite a lot to make Toby feel like he’s starting a new life. In a way, he is. But going through a divorce with children means that one will never truly be free from that old life. Indeed, it is Toby’s soon to be ex-wife who hovers, ghost-like, over the pages in the first two-thirds of the book. We get to know Rachel mostly through the prism of Toby and his friend, Libby (who narrates this tale). And it’s through that lens where Rachel is painted as a driven, career-obsessed, somewhat cold woman who doesn’t care all that much for her children — but does have an endless amount of energy for her PR firm. Since we only get to know Rachel from how others see her (mostly Toby), we don’t know the mystery of why she drops off the kids at Toby’s home one morning, and then cuts off all communication with Toby after going to a yoga retreat for almost a month. Toby is now a single parent who has to juggle his work while taking care of his tween daughter Hannah and six-year-old son Solly. Kids at that age can be more or less self-sufficient, but one still has to feed them, get them to school, pick them up, help with homework and all the other million small things that come with raising kids. Toby isn’t a checked out dad, however. He’s been the primary caregiver during the entire marriage, and while having to care for the kids most of the time cuts into his dating life, he attends to his responsibilities without too much grumbling. Toby is also trying for a promotion at work, managing a patient with a rare liver condition, mentoring his junior staff, and realizing that an 11-year-old daughter’s life with and without social media can be a nightmare.

There are also subplots with Libby and another friend Seth — who is inching toward “The Institution” at the same time she and Toby are exploring what life is like free of its bonds. But what of Rachel? Having a character who seemingly causes the chaos and conflict that moves the plot forward is a bit of a mystery. Why would she just drop off the kids at Toby’s place — and then want nothing to do with them? Where did she go? Why won’t her staff tell Toby anything about her whereabouts? We feel Toby’s frustration throughout the novel because that’s really the only perspective we get. It’s not until the final third of the novel when the reader understands who Rachel is and why she just kind of disappeared from her family, job, and life. Keeping that “big secret” until the end was a deft stroke by Brodesser-Akner because she was able to build up an image of Rachel for almost 300 pages, only to reveal a very different side to her personality that no one understood — not even Toby.

Fleishman is in Trouble isn’t a masterpiece, but Brodesser-Akner is often masterful in capturing part of a generation at a particular period of rapid change. She is very sharp in her witty observations about wealthy people, dating apps, social media, and career anxiety in New York City. But underneath her critique on the coldness of sex without intimacy, there’s a sense of hope that life at 40 isn’t a downhill slide. Sure, people aren’t as attractive as they were in their 20s, but she seems to be saying that while a good romp (or many romps) in the sack with someone new has short term psychological and physical benefits, apps can’t replace what we really want as humans: companionship without conflict.