Fleishman Is in Trouble

Toby Fleishman wakes up to a text from his ex-wife, Rachel, informing him that she is headed to a place called Kripalu and that their two children are at his apartment. Toby checks and sees that his children are, in fact, in their beds, and then he calls Rachel. They argue over whether this was an irresponsible thing for Rachel to do, with Toby believing strongly that it was.

Toby wakes up his two children, Solly, a nine-year-old boy, and Hannah, an 11-year-old girl. They eat breakfast and then walk to the Y together, where Toby drops the two children off for camp for the day. While still at the Y, Toby is approached by Cindy Leffer, a friend of Rachel’s who also has small children. Toby gets the feeling that Cindy has taken a new, possibly sexual interest in him since he and Rachel separated. Toby leaves the Y and walks toward the park. As he walks, he checks a dating app and swipes right on a woman whose picture shows her lying in bed with her breasts partially exposed.

Toby receives a phone call from Joanie, one of the fellows Toby is training at the hospital. Joanie tells Toby that they have a consult in the ER. He tells Joanie he will be at the hospital in 20 minutes and then hangs up. He sees a text message from a woman named Tess, with whom he confirms dinner plans for that night, even though he will have to leave his kids behind in order to go on the date. He hates Rachel for putting him in this position.

Toby arrives at St. Thaddeus hospital, where he works as a doctor specializing in liver treatment. In the ER, he sees an unconscious 44-year-old woman named Karen Cooper. Karen Cooper is blonde and wearing a satin dress. A tall man in his 40s named David Cooper waits beside her. Toby asks the man what happened to her. The man says that Karen Cooper spent the weekend in Las Vegas with her best friend. When she came back, Karen Cooper was clumsy and woozy, as though she was still drunk from her trip. She began to slur and say odd things to David Cooper. She looks yellow and Toby announces that she is jaundiced. After having David Cooper escorted out of the room, Toby consults with his fellows to discuss what Karen’s diagnosis might be. Joanie suggests that Karen Cooper has Wilson’s, a rare liver disease. Toby continues to do his rounds in the hospital, seeing and treating various patients. He feels a hand on his shoulder. It’s Joanie. She shares her surprise and interest in receiving a Wilson’s case.

The narrator of the novel meets up with a friend named Seth in the city. Seth is tan and has white teeth and is attractive, although he looks different than he did in college, when he, the narrator, and Toby became friends. Toby arrives at the same restaurant. Over a meal, they talk about Seth’s recent sexual escapades and his new relationship with a woman named Vanessa. They take turns cursing Rachel, a ritual they perform on certain people as an inside joke.

Toby takes his two children to synagogue. For dinner, they eat takeout from the deli. Solly talks about how many kids will not be returning to day camp at the Y the following week because they will all be going to sleepaway camp instead. After dinner, Toby showers and prepares for his date, and then walks to a bar called Dorrian’s on Second Avenue. His date’s name is Tess. She has dyed blond hair and is drinking a martini when he walks in. He watches her to see if his shortness will be a turnoff for her, but it doesn’t seem to be a problem. Tess and her husband split up after her husband became interested in having threesomes that excluded her. After drinks, Toby and Tess go to her apartment and have sex. Toby believes that he is not necessarily very important or special to Tess; he thinks she is merely interested in sex. He realizes that he is nevertheless enjoying it as well.

The next morning, as Hannah and Solly eat pancakes and watch cartoons, Toby texts Rachel, asking her when she plans to pick up the children. She doesn’t respond. He gathers the children and they walk to the park. Along the way, a rich-looking boy smiles and says hello to Hannah, and Hannah says hello back. When Toby asks who the boy was, Hannah yells at him, embarrassed that they are walking instead of taking a cab to the park. Solly asks Toby why Hannah is so angry, and Toby responds that he doesn’t know.

That night, Toby walks with Solly and Hannah to Cyndi and Todd Leffer’s apartment on 79th and Park to drop Hannah off for a sleepover with their daughter, Lexi. Todd and Cyndi invite Toby out to lunch at a club the following week and remind him that they are not only Rachel’s friends but also his. On the walk back to his apartment with Solly, he continues to text Rachel to ask where she is, but she doesn’t respond.

The next day, Hannah takes a haftorah lesson with a rabbinic student in the apartment while Solly watches a movie. Toby alternates between texting women he’s interested in and texting angry messages to Rachel asking where she is. At the end of the day, he texts Mona, the family’s long-time nanny, asking if she can take care of the kids the next day. Mona writes that she hoped to spend the week visiting with her son. Toby pleads and ultimately persuades her to come by for a few hours. When Hannah asks about Rachel’s whereabouts, Toby answers ambiguously rather than admitting that he hasn’t heard from her.

At the hospital, Toby confirms to David Cooper that his wife Karen Cooper does indeed have Wilson’s disease. After delivering the diagnosis, Toby berates his interns for looking at their notes rather than looking David Cooper directly in the eye as they were giving him the diagnosis. He then goes to his office to call Kripalu, the retreat Rachel is at, but the woman he speaks to refuses to provide Toby with any information about Rachel’s whereabouts. When he goes home, he discovers that Solly has been watching pornography on a computer in the living room. He spends two hours comforting Solly and reflecting on how difficult it is to grow up.

Hannah comes out of her room that Tuesday with her bags packed, expecting to be taken to the Hamptons by her mother, Rachel. All her friends are already there. Toby tells Hannah that Rachel has taken a work trip. Hannah is enraged by the news. He texts a woman named Nahid to postpone their date. Later that night, Toby fires the nanny, Mona, via text, citing the fact that Solly watched pornography under her watch.

The next morning, Toby brings both Solly and Hannah to the hospital, where they wait in a conference room while he works. Toby meets with the chief of hepatology, Donald Bartuck, in the chief’s office; Donald is tall and muscular and powerful. Toby requests a couple of days off from work for personal reasons. Bartuck tells him that it isn’t ideal for him to be taking time off because Karen Cooper’s husband is an important man. Toby persuades Bartuck to grant him two days of leave anyway.

Toby drives Solly and Hannah to their house in the East Hamptons. Toby dreads the Hamptons and feels the large, fancy homes are more representative of Rachel’s desires than his own. While there, Toby talks on the phone with Simone, Rachel’s assistant. Simone tells Toby only that she’ll leave word with Rachel that he called.

Toby drives Hannah to playdates, and he walks with Solly on the beach. He sexts with Nahid. When he drops Hannah off at a playdate, a girl’s mother, Roxanne Hertz, asks why Toby is the one in the Hamptons when Rachel kept the Hamptons house in the divorce. Toby tells her that Rachel has left town for a little while. As they talk, Roxanne tells Toby, “Well, you know how new relationships are. I’m sure you’ll get into a routine” (124). Later, as Toby is driving, he reflects on what these words could mean and realizes that Roxanne might be implying that Rachel has been spending time with another man. He begins to feel panic. When he gets back home, he jumps naked into the backyard swimming pool.

On Sunday, Toby drives with the kids back to the city. He buys Hannah a new phone, which she had been asking for repeatedly. He makes plans with Nahid and, now that he has no permanent babysitter, Toby calls up the director of the sleepaway camp and asks whether there is space for a fourth grader. The director tells him that it is too late to sign up, but Toby convinces him to inquire whether there might be space anyway. Toby then tries to persuade Solly that he would have fun at sleepaway camp, although Solly shows signs of resistance.

Back at the hospital, Toby consults with his fellows about Karen Cooper’s case. She is number 12 on a transplant list and still unconscious. Her two sons wait by her side. While talking about her case with David Cooper, Toby receives a text from the camp director informing him that there is space for Solly at sleepaway camp.

Toby stops by Rachel’s apartment with the kids to pick up clothing. That night, he leaves the children at the apartment with a babysitter and goes to Nahid’s apartment for the first time. He is pleasantly surprised to find that she is not only a real person, but attractive as well. He sleeps with her, and instead of taking a cab home, he “stomped through the park, feeling big and tall and virile, like he owned this city and that it was all for him and that, once again, he was at the beginning of something profound and new” (141). At home, he finds Hannah sitting on his bed, crying. Hannah texted her mother, but Rachel didn’t respond. Toby comes up with excuses as to why Rachel hadn’t texted, still withholding the truth, which is that Toby hasn’t heard from her and doesn’t know exactly where she is.

As they prepare to leave for sleepaway camp the next morning, Toby fields more sexually explicit texts from Nahid, and then asks to see Hannah’s phone so that he can check her internet profiles. Hannah is angry but lets him. Solly feels excited for camp but asks if Toby will be lonely without them. Toby tells Solly that he’ll miss him but will be able to get a lot of work done.

Toby drops the children off at the bus stop. They are taken away for a weeks-long overnight camp, finally giving Toby some space and freedom. He goes to Nahid’s apartment. The next day at the hospital, Joanie approaches Toby in his office in a way that he interprets as possibly expressing romantic interest, and he fantasizes about Joanie as a possible partner. He meets with his boss, Bartuck, who assures Toby that he will be promoted the following week.

Toby leaves work and walks through the park. He sits on a park bench and checks his dating apps. He gets in a verbal altercation with a man who lights a cigarette nearby him, even though they are sitting in a no-smoking area. Toby reflects that he misses Solly and walks aimlessly through Manhattan. He enters a grocery store and runs into Cyndi Leffer and Miriam Rothberg. Miriam tells Toby that she and Cyndi had just seen Rachel in the park that day, sleeping on a blanket in the open.