Fleishman is in Trouble

divorce -
solitude -
A Relentlessly Clever Storyteller Bares Life in Manhattan, Warts and All
Taffy Brodesser-Akner
Penguin Random House
Publication Date
Jun 18, 2019
Number of Pages
Fiction Nominee - National Book Award (2019), Longlisted - Women's Prize for Fiction (2020), Fiction Nominee - Goodreads Choice Award (2019), Debut Novel Nominee - Goodreads Choice Award (2019)

Image: Fleishman is in TroubleIn her debut novel, Taffy Brodesser-Akner unearths the remains of the American dream by probing at the loneliness of one man and two women amidst the disintegration of a marriage – all living in a strata of society where empathy and kindness are rare.

At the beginning of the novel, Toby Fleishman is still coping with his divorce from his wife, Rachel. Our story follows Toby as he is pressured to move on from his relationship with his ex-wife. We are introduced to Libby, one of Toby’s childhood friends and the chronicler of his thoughts. We only meet Rachel through Toby’s memory for most of the book. We also see Toby try to juggle being a father and working as a hepatologist, or liver specialist. As they try to navigate life in Manhattan, an urban landscape marked by an ongoing rat race, Toby, Libby, and Rachel are met with anxiety and stress.

Brodesser-Akner tells a nuanced story about the end of a relationship in Fleishman is in Trouble, exposing the common hypocrisies in our daily routines. The stream-of-consciousness writing style calls on the reader to reflect on our own own experiences with society. Brodesser-Akner’s characters are drawn from everyday life, capturing the ambition, mercilessness, and rampant contempt familiar to those living in a city. There is a surgical precision to how each character perceives others – perhaps a result of the author’s roots in journalism. 

Toby’s character professes himself to be committed to doing the right thing, even as he reels from the pent-up emotions of his acrimonious divorce with Rachel. He tries to find a way out of the trappings of his status as a wealthy doctor, and finds solace in various dating apps to try to escape his solitude. Brodesser-Akner sketches Toby as a well-intentioned 41-year-old dwelling on the decisions that led to emotional trauma and all their possible alternatives. That self reflection made me feel compelled me to be on Team Toby. Feeling skeptical of making this decision too quickly, though, I struggled to reserve judgement until the conclusion of the story.

When Rachel leaves town, dropping off their 11-year-old daughter and 9-year-old son in Toby’s care, his recently-established routine of meeting women for a series of one-night-stands is turned upside-down. As he decides to prove himself the responsible parent, Toby reconnects with friends from his teenage years: Libby, a former journalist for a men’s magazine, and Seth, a classic playboy stock character. 

As the pace of the story accelerated, following the arrival of Toby’s kids, I was drawn into Brodesser-Akner’s comic tone. The novel’s subtext takes apart our complete lack of self-awareness in a world where digital privacy barriers were traded for hyper-connectivity a long time ago. To me, Fleishman is in Trouble is the spiritual successor to Richard Yates’ Revolutionary Road, diving into the whirlpools of confusion, bewilderment, and disorientation within contemporary family life. In 2020, this book feels like an authentic portrayal of how we misuse our power in relationships with those closest to us without realizing what we’re doing.

If we all pledge to ask ourselves “Have I considered whether I’m just being an asshole?” on a frequent basis, maybe we’ll be able to see how things come across to another person – especially in a close relationship. After I finished Fleishman is in Trouble, I spent some time reflecting on my own past. As a cisgender, “straight-passing” queer man, I’ve exploited my privileged position in society in one instance too many over the years. I have a long way to go in challenging my own privilege, something that the book asks every reader to consider.

Brodesser-Akner makes it very clear: the patriarchy is as real as it is pervasive. Pretending that everything will be alright because we’ve made progress is a delusion we repeat to ourselves to hide our own dirty laundry. 

About the Contributor

Maulik is a sometimes actor, writer, and entrepreneur. He likes to put his nose in art that makes you lose track of time, especially if it's a comedy and/or romance. He is an agnostic film buff with a soft spot for indie films and web series. When he finds a spare moment from dislodging people's comfort zones without warning, Maulik can be found marveling at everyday relics of colonial racism – at any time of day or night.