Fleishman Is In Trouble is a book by Taffy Brodesser-Akner. The Fleishman family is made of four people: dad Toby, mom Rachel, children Hannah and Solly.
This post is full of spoilers, including the ending of the book. If you are looking for a review, visit this post instead. This post isn’t sequenced as in the book. The book goes back and forth in time, between different points in the past and the “present day”.
Rachel is a business owner and Toby a hepatologist. After being together for 15 years, they are going through a messy divorce. Their relation had devolved into throwing things and shouting before they finally separated.
The Happy Years
In college, Toby struggled to find love and connection. When he met Rachel, it was a turning point in his life. Her drive and ambition helped him become more successful too.
Toby proposed to Rachel on a trip to visit her in Budapest. She was there studying during the fall semester of her senior year. They got married in Los Angeles, organized by his mother at the synagogue where she served on the board. It was Toby’s mother’s chance to create a big show to impress the community.
When Toby and Rachel separate, their views of the world are oceans apart. Rachel thinks that she’s misunderstood and that this is largely because she is woman who runs her own business. She’s driven to be successful and for her children to be part of the in crowd, able to hold their own with the rich children. Toby doesn’t see the dark spaces in her, the ones from growing up with a distant grandmother, and attending a school where she couldn’t afford to have friends. She wants to be rich because of the opportunities it affords, and she loves her job. She’s also frustrated by Toby’s lack of ambition and his disdain for her work, even though he enjoys the life she is able to provide with her salary. He makes a good salary, but she outearns him.
Rachel had a traumatic first childbirth. The delivery didn’t go as planned and the doctor ruptured the membrane inside her uterus with no advance notice. She got PTSD as a result and never got the help that she needed. The only place she felt some solace was at a rape support group, where she just listened to other people’s stories.
Rachel wanted children and loved them, but had to recover after each pregnancy. She was also happy to let Toby be the primary caregiver.
At 14, Toby was a short, chubby kid and ashamed of himself. In response, his mother took him to Weight Watchers with her. He was drawn in by his success on the plan and kept it up until he stopped eating carbs entirely at 24. He also started exercising back then.
Toby didn’t had much success with girls before Rachel, When he met her during his first year of medical school. He was attracted to her as much for her unconventional looks as a Jew, looks that she inherited from “her absent Gentile father”.
Now, Toby thinks that Rachel is aggressive and careless. He chose here because she was not crazy; he wanted to avoid a crazy wife. Now, he thinks back to the early years when they were dating, trying to find any warning signs that he missed. He considers Rachel to be a bad mother and a bad wife because she pushes him to be more ambitions and works long hours rather than spending more time with their children. She isn’t as nurturing and he wants her to be.
After their separation, Rachel disappears one day and is gone for weeks. She drops off the children at Toby’s while he is asleep, answers the first call from him, and then avoids all other calls. She doesn’t show up to pick up the children at the end of the weekend when it’s her turn to have them. Instead, Toby takes time off from work for childcare and to take them to the Hamptons. Finally, he sends them off to sleep camp.
Sleep camp is cut short when Hannah is sent home for sexting with one of the boys at the camp. Toby, angry that only Hannah is being sent home and not the boy, takes both children home. He enrolls them back in day camp, which they had attended earlier in the summer, but Hannah is mortified that everyone knows what she did. Toby then takes them to work with him and sets them up in a conference room.
Toby is expecting a big announcement. He dresses carefully and brings the children to work one day, expecting news of a promotion to department head. Instead, someone from outside the hospital is hired, his old classmate and nemesis. His boss explains that he has a reputation as someone who watches the clock, and he hasn’t shown much dedication to the hospital in recent weeks. He wasn’t there when one of his patients has a major event happen, and he kept quite regular hours. Toby wanted the promotion and thought he deserved it.
In his loneliness, Toby imagines that his intern, Joanie, is interested in him. He creates a whole story in his head about the life they could have together, particularly how good she will be for his children. When he does ask Joanie out for dinner, she declines. Although he keeps his distance after her rejection, he still fixates on her.
Friends and Connections
As his marriage falls apart, Toby resurrects his friendship with two friends from a year abroad in Israel during junior year of college. Elizabeth (Libby) is having a midlife crisis. She’s become frustrated by the sameness of her life, and reconnecting with her college friends is a reprieve. For the other friend, Seth, he’s a free spirit who may finally be ready to settle down after years of playing around. When the four of theme reconnect, they rediscover the relationship of their youth, and some of that freedom with it.
Libby has trouble seeing herself through Toby’s eyes, reconciling the girl she was with the woman she has become. To compensate, she spends more time with Toby and Seth, keeping secrets from her husband, Adam, about her activities. She’s taken up smoking again, and vaping weed with a vape pen that Seth couriered to her.
Rachel and Toby moved on from their marriage in different ways. Rachel had an affair with the husband of a “friend” until she realized that he also wasn’t interested in getting to know her as a person. He was looking for someone one-dimensional. She realized that he complained about his heiress wife but didn’t really want anything else, that he wasn’t willing to support her in moments of need. While they were away for a weekend together at a yoga retreat, he expected her to orbit around him. Their relationship breaks up, and she stays behind at the retreat when he leaves.
When Toby is not with his old friends or his children, he’s on his online dating app. His interns installed the app for him once he and Rachel separated. Initially, it’s exciting meeting and hooking up with different women. But then he finds it exhausting, and lonely. On a whim, he decides to get a dog. It will provide him some company and the kids will like it. He also whittles his playdates down to one, Nahid, a Parisian woman who lives several blocks from him. They have a discrete, clandestine affair. Although she is separated, her husband doesn’t want a divorce for the sake of appearances. Toby pestering her to go out on a day, and one day, she acquiesces. When to do go out for lunch, Toby realizes how little they have in common, and he can’t wait to get away.
While Rachel was gone, her business fell apart. She’d buried her phone and been unreachable. Upon her return, she drops by her biggest client’s home early one morning, unable to sleep and unaware of the time. This is how she learns that she had lost that client to the agency she left to create her own business. She’d poached that client and now lost her.
After spending all day away from home, and sleeping at Toby’s after a night out, Elizabeth ran into Rachel. Rachel shares her side of the story with with Libby, ending with her mental breakdown. She’s unable to sleep, and still spiraling. We learn her perspective, of Toby’s selfishness and lack of understand. Libby had been making some similar recent observations about Toby. Libby took Rachel home and watched over her while she slept. After doing this for several days, Libby hired someone to babysit her. She called Toby to tell him the state that Rachel was in, but he showed no interest in helping her.
The Ending of Fleishman Is In Trouble
Seth has an extravagant party to announce his engagement. As Libby leans outside waiting for Toby for them to leave the party together, she realizes how lucky she is. She loves her husband and children, and she wants to recommit to them, to repair any fissure she may have caused while trying to live a different life for the past few weeks. Making her decision, she calls a taxi and heads home.
I would wonder, globally how you could be so desperately unhappy when you were so essentially happy.
I had worked at a men’s magazine, trying to do work I could be proud of, only to learn that a woman at a men’s magazine is like a woman in the world – unwelcome, auxiliary at best, there to fill in the rough spots that men don’t want to.
Toby gets back outside to find Libby gone. He walks until it starts to rain and then takes the train home from Union Station. After taking a shower to rinse the smell of weed off him, he makes some decisions about next steps. He will move to an apartment where everything works, and he will survive. He considers how too much of a good thing could be just as bad as a bad thing, optimism versus loneliness, but is happy he’s had some optimism tonight. While talking at the party with Libby, he realized that he wants to marry again someday. He stands in his apartment being mindful, grounded in the moment, when Rachel uses her key to open the apartment door.
The Telling of the Story
Libby is the narrator in Fleishman Is In Trouble. This is the book that she eventually writes after leaving her job at the men’s magazine where she worked for years. She didn’t feel that she fit in there anymore.. She’s friends with Seth and Toby, so she knows their stories to be able to tell it. After the separation, Libby sees Toby clearer than ever before. When she meets Rachel, she gets to fill in the blanks of Rachel and Toby’s life, what led to the separation and Rachel’s disappearance.