Fleishman Is in Trouble is the debut novel by journalist and writer Taffy Brodesser-Akner. Originally published in 2019, it is a satiric novel work of domestic fiction. The book was long listed for the 2019 National Book Award. This guide references the June 2019 hardcover edition by Penguin Random House.

Plot Summary

The story is told by a narrator, Libby, who speaks in both third and first person. Rachel and Toby Fleishman, professionals in their 40s who live in Manhattan, have gotten a divorce. Together, they have two children: Hannah, an 11-year-old girl, and Solly, a nine-year-old boy. Rachel secretively dropped Hannah and Solly off at Toby’s apartment without any forewarning. When the day comes around for Rachel to pick the children up again, she is nowhere to be seen. Toby is unable to reach her by phone or through her assistant.

While Toby tries desperately to ascertain Rachel’s whereabouts, he attempts to meet his responsibilities at work (he is a hepatologist at a hospital and has a patient with a rare condition) while also trying to meet his children’s needs in the wake of their mother’s sudden disappearance. All the while, Toby goes on dates with women from his dating app, including a woman named Nahid, who becomes his main romantic interest.

Toby fires his nanny after Solly watches online pornography. Despite being up for a promotion and needing to be near his patient, he takes a few days off and brings his children to the Hamptons. After they return to the city, he sends his children away for summer camp. Two of Rachel’s friends tell Toby that they spotted Rachel sleeping on a blanket in the park.

Toby confirms that Rachel has been seeing a married man named Sam Rothberg. Meanwhile, Toby’s patient, Karen Cooper, undergoes surgery. With Rachel still nowhere to be found, Toby is forced to pick up Hannah and Solly from summer camp after Hannah sends a sexually explicit photo to another boy at camp. On the drive home, Toby admits to his children that he doesn’t know where Rachel is. Back at work, Toby fails to receive the promotion. He makes a pass at one of his colleagues, who rebuffs him.

Karen Cooper dies after complications from surgery. Toby has second thoughts about dating Nahid. Meanwhile, the narrator runs into Rachel while grabbing coffee and a bagel and listens to her story. It turns out that Rachel hasn’t slept for more than 10 days and is in the midst of a sort of delirium. The narrator takes Rachel to her home and puts her to sleep before calling Toby and telling him what happened. At the novel’s end, Rachel returns home.