Fleishman Is in Trouble

Taffy Brodesser-Akner

Fleishman Is in Trouble

Taffy Brodesser-Akner
37 pages1-hour read
Fiction
Novel
Adult
Published in 2019

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Character List

Meet the key characters, with insights into their roles, motivations, and relationships—spoiler-free.

Major Characters

Toby is a hepatologist at St. Thaddeus hospital who recently separated from his wife of 15 years. He attempts to fulfill demanding professional responsibilities, including treating a rare Wilson's disease case, while meeting his children's needs in the wake of their mother's sudden disappearance. Having felt physically insecure in his youth, he heavily uses dating apps, swiping on women whose online personas often differ from their real-world selves.

Key Relationships

Former Wife of Rachel Fleishman

Father of Solly Fleishman

Friend of Seth

Supervisor of Joanie

Doctor to Karen Cooper

Date of Nahid

Rachel is a highly successful talent agent who built her own company after facing workplace sexism early in her career. Raised by an emotionally cold grandmother, she places immense value on financial security, networking, and social mobility. Her sudden retreat to Kripalu sets off a logistical crisis for Toby, who views her ambition as a personal failing.

Key Relationships

Former Wife of Toby Fleishman

Mother of Solly Fleishman

Romantic Interest of Sam Rothberg

Employer of Simone

Agent for Alejandra Lopez

Hannah is Toby and Rachel's 11-year-old daughter. She reacts to her parents' divorce with outward hostility, frequently clashing with her father over minor inconveniences like walking instead of taking a cab. She depends heavily on her mother and struggles to manage her anger as Rachel's absence lengthens.

Key Relationships

Daughter of Toby Fleishman

Daughter of Rachel Fleishman

Older Sister of Solly Fleishman

Friend of Lexi Leffer

Solly is the nine-year-old son of Toby and Rachel. Unlike his sister, he processes the sudden changes in his family dynamic internally. He maintains a sweet disposition, showing curiosity about the world and offering quiet reassurance to his father while avoiding outright rebellion.

Key Relationships

Younger Brother of Hannah Fleishman

Ward of Mona

Libby is a former men's magazine journalist who lives in the New Jersey suburbs with her husband and children. She acts as both an observer of Toby's life and an active participant in his social circle. She formerly worked at a men's magazine, an experience that informs her critical perspective on gender dynamics in relationships.

Key Relationships

Friend of Toby Fleishman

Friend of Seth

Acquaintance of Rachel Fleishman

Seth is a bachelor who became close friends with Toby and Libby during college. He works in finance but faces recent professional instability. He enjoys an active dating life and represents the kind of unattached freedom Toby is just beginning to experience.

Key Relationships

Friend of Toby Fleishman

Boyfriend of Vanessa

Supporting Characters

Sam is a wealthy, well-connected businessman. He moves comfortably among the upper echelons of society, wielding influence through his money and social standing. He views ambition as an attractive quality and routinely mixes his professional power with his personal interests.

Key Relationships

Romantic Interest of Rachel Fleishman

Husband of Miriam Rothberg

Acquaintance of Toby Fleishman

Nahid is an Iranian woman who immigrated to the United States as a child. She connects with Toby on a dating app, sending him sexually suggestive messages. She keeps her personal life strictly contained within her apartment, refusing to be seen in public due to an ongoing separation from her husband.

Key Relationships

Romantic Interest of Toby Fleishman

Cyndi is a wealthy mother embedded in Manhattan's elite social circles. She represents the superficial, status-obsessed lifestyle that Toby dislikes but Rachel aspires to join. She occasionally offers Toby unwanted attention or social invitations following his separation.

Key Relationships

Acquaintance of Toby Fleishman

Wife of Todd Leffer

Mother of Lexi Leffer

Miriam is Sam's wife and a highly influential figure in Rachel's desired social sphere. Her immense wealth dictates her lifestyle, though her husband privately complains about her lack of professional drive.

Key Relationships

Wife of Sam Rothberg

Acquaintance of Rachel Fleishman

Friend of Cyndi Leffer

Joanie is a young, dedicated medical fellow training under Toby at St. Thaddeus hospital. She demonstrates sharp clinical instincts and genuine enthusiasm for complex medical cases like Wilson's disease.

Key Relationships

Subordinate to Toby Fleishman

Karen is a 44-year-old woman admitted to the hospital following a weekend trip to Las Vegas. She suffers from Wilson's disease, a rare liver condition that requires intensive medical intervention. Her unconscious state leaves others to speak for her.

Key Relationships

Wife of David Cooper

Patient of Toby Fleishman

Friend of Amy

David is a tall, important man who brings his wife to the hospital when she exhibits bizarre symptoms. He demands clear answers from the medical staff and struggles to understand the severity of his wife's condition.

Key Relationships

Husband of Karen Cooper

Acquaintance of Toby Fleishman

Donald is the tall, muscular chief of hepatology at St. Thaddeus. He holds significant authority over Toby's career advancement and prioritizes the satisfaction of important patients' families.

Key Relationships

Manager of Toby Fleishman

Simone is Rachel's professional assistant. She acts as a strict gatekeeper, shielding her boss from unwanted inquiries and managing her logistical needs.

Key Relationships

Assistant to Rachel Fleishman

Contact for Toby Fleishman

Mona is the Fleishman family's longtime nanny. She provides essential childcare but eventually runs afoul of Toby's strict disciplinary expectations when an incident occurs under her watch.

Key Relationships

Employee of Toby Fleishman

Caretaker of Solly Fleishman

Former Employee of Rachel Fleishman

Vanessa is Seth's young, warm, and highly attractive girlfriend. She integrates smoothly into Seth's friend group and provides a stabilizing presence in his otherwise chaotic bachelor life.

Key Relationships

Girlfriend of Seth

Acquaintance of Toby Fleishman

Tess is a woman with dyed blond hair whom Toby meets at a bar called Dorrian's. She recently separated from her husband due to differing sexual interests and engages in a brief, casual encounter with Toby.

Key Relationships

Todd is Cyndi's husband, embedded in the same wealthy social strata as Sam Rothberg. He attempts to maintain cordial ties with Toby despite Toby's disdain for their social circle.

Key Relationships

Husband of Cyndi Leffer

Acquaintance of Toby Fleishman

Lexi is the daughter of Cyndi and Todd Leffer. She provides Hannah with an escape from Toby's apartment through sleepovers.

Key Relationships

Daughter of Cyndi Leffer

Barbara is Toby's lawyer. She occasionally forgets the specifics of his case and offers contradictory advice, highlighting the chaotic and uncontrollable nature of his legal situation.

Key Relationships

Lawyer for Toby Fleishman

Amy is Karen's best friend. She accompanied Karen on a trip to Las Vegas and provides Toby with crucial personal context about Karen's unhappy marriage.

Key Relationships

Friend of Karen Cooper

Acquaintance of Toby Fleishman

Alejandra is a famous stage actress whose career Rachel launched. Her success firmly established Rachel's reputation and financial independence in the talent agency world.

Key Relationships

Client of Matt Klein

Matt is Rachel's former employer and current industry rival. He represents the systemic sexism Rachel faces, having penalized her for pregnancy before later poaching her star client.

Key Relationships

Former Manager of Rachel Fleishman

Agent for Alejandra Lopez