Fleishman Is in Trouble

The novel’s other protagonist, Rachel is Toby’s ex-wife and the mother of Hannah and Solly. Ambitious and successful, she is the founder of a respected talent agency. She was raised by an emotionally cold grandmother from a young age. At the beginning of the novel, Rachel secretly drops off Hannah and Solly at Toby’s apartment without warning him and then escapes to a retreat called Kripalu with a man named Sam Rothberg. She then disappears for three weeks, setting up the novel’s plot.

Seen from Toby’s perspective, Rachel is emotionally distant from her children and overly ambitious about work. From the narrator’s perspective, Rachel is highly competent and successful, someone who is unfairly villainized for her ambition. Rachel experienced a difficult labor with Hannah, which affected their bond. Hannah struggles with a preoccupied attachment to her mother and finds Rachel’s absence particularly challenging.  

Hannah is Toby and Rachel’s 11-year old daughter. She is often angry at Toby and prone to arguing with him, and she misses her mother deeply. In the chaos of her parents’ divorce, Hannah engages in risky behavior, including sending a sext to one of the boys at her summer camp.

Solly is Toby and Rachel’s nine-year-old son. He is sweet, curious, and supportive of Toby, and he doesn’t rebel, even when he’s forced to leave the summer camp he’s been enjoying after his sister is dismissed. Where Hannah expresses frustration with her parents’ divorce and the disruption to her life outwardly, Solly keeps his feelings within.

The novel is narrated in first-person by Libby, a college friend of Toby and Seth. Libby is in her 40s. A wife and mother living in the suburbs of New Jersey, she is formerly a journalist at a men’s magazine. She alternately has empathy for and is critical of Toby’s behavior. She tells Toby’s story in a close third person while also occasionally entering the story as a first-person character in the narrative. As she observes Rachel and Toby’s challenges, she resolves to return home and work on being a better partner and parent.

Seth is a college friend of Toby. A bachelor, he is attractive, playful, and has womanizing tendencies. Seth falls in love with a woman named Vanessa and proposes to her toward the end of the novel. He has lived the free life that Toby is just now experiencing, and he’s ready to settle down.

Sam, Rachel’s primary romantic interest in the novel, is married to Miriam. Sam is extremely wealthy but also superficial and vapid. He tells Rachel he values her ambition but leaves her in Massachusetts when she doesn’t service his needs during a romantic vacation. Rachel wants to be part of Sam’s world, but being with Sam introduces her to that world’s harsh reality.

Toby meets Nahid, his primary romantic interest, through a dating app. Although he frequently visits her apartment for sex, she is still married to someone with whom she intends to separate. She and Toby frequently exchange sexts, a slightly uncomfortable parallel to the explorations that Hannah and Solly are beginning to have online. When they finally go out on a real date—in the real light of day—Toby finds their conversation flat, and Nahid’s appearance is not as it seemed to be. Fantasy never quite measures up to reality, whether after a few weeks or after 15 years of marriage.

Cyndi Leffer is the mother of one of Hannah’s friends, and a friend of Rachel’s. She represents the rich, superficial set of people that Rachel aspires to join but that Toby despises.

Miriam is even more wealthy than her husband Sam and extremely influential. Rachel aspires to become close friends with her before becoming involved with Sam. 

Joanie is one of Toby’s fellows at the hospital. She is much younger than he is, but she shows curiosity, character, and intelligence. He fantasizes about Joanie as a romantic prospect, and their intimate conversations contrast sharply with his shallower dating app adventures. Toby finally asks Joanie on a date, but Joanie turns him down in no uncertain terms.