By – July 1, 2019

Toby Fleish­man is in the midst of a cri­sis. His soon-to-be ex-wife Rachel has dis­ap­peared, leav­ing their two chil­dren with him; he’s on the cusp of a pro­mo­tion, but can’t seem to stay in the office long enough to make it clear that he is wor­thy of it; he’s hook­ing up with ran­dom women who send him pic­tures of their under­wear and their bras to entice him, in order to sat­is­fy his need to be want­ed. All the while he strug­gles with self-loathing and the nag­ging feel­ing that his mar­riage fell apart because he’s too short and too unambitious.

At least, that’s how Toby is pre­sent­ed. Toby’s saga is told through his friend Lib­by Epstein, who he recent­ly re-con­nect­ed with after years of dis­tance. Now that Toby is sep­a­rat­ed from Rachel, he needs a woman he can talk to about his ex-wife and about his strug­gle. His dif­fi­cul­ty. His hard, stress­ful life. Which Lib­by tells, duti­ful­ly, for most of the novel.

But as the book goes on, the read­er learns more about Lib­by. She is a writer, for­mer­ly of pro­files for a famous men’s mag­a­zine, and cur­rent­ly as a writer of a young adult nov­el she can’t fin­ish. Lib­by finds inspi­ra­tion in Toby’s sto­ry, set­ting it up like she would one of her pro­files. The book begins as a sto­ry about Toby, and becomes a sto­ry about her­self — as she her­self says, Tro­jan horse your­self into a man, and peo­ple will give a shit about you.”

And so, through Toby, we learn about Lib­by. How she feels like she’s at an impasse, like she’s stuck in a won­der­ful life she chose for her­self. Toby’s angst at his dif­fi­cult, up-in-the-air life throws her own set­tled life into sharp relief. She’s a stay-at-home mom, just like the oth­er moth­ers in her neigh­bor­hood. She isn’t young any­more and she won’t be young again — she isn’t a Great Writer, and may nev­er become one. She seeks Toby out, try­ing to recap­ture a part of her­self now lost — the girl who smoked, who stayed out late, who didn’t have a hus­band and chil­dren and a home in New Jer­sey wait­ing for her.

And what about Rachel? The read­er doesn’t real­ly know much about her, except for Toby’s account and Libby’s telling over of it. That is, until the moment Rachel and Lib­by bump into each oth­er — and the read­ers under­stand­ing of the sit­u­a­tion is shift­ed once more.

All that is to say Fleish­man is in Trou­ble is a fas­ci­nat­ing nov­el that exam­ines the intri­ca­cies of being a good par­ent, the seduc­tive pow­ers of ambi­tion and mon­ey, and the dif­fi­cul­ty of keep­ing up appear­ances and fit­ting into a com­mu­ni­ty. It allows the read­er to be a fly on the wall, an observ­er to all of Toby and Rachel’s mis­takes and mishaps, while allow­ing for empa­thy and under­stand­ing in the face of immea­sur­able stress. This book is not about being Jew­ish but is instead so inher­ent­ly Jew­ish, with inti­mate knowl­edge of the com­mu­ni­ty woven through­out that can only be por­trayed by some­one right inside of it.

Fleish­man is about divorce and tru­ly see­ing peo­ple — see­ing the per­son you are mar­ried to, see­ing your friends for who they real­ly are, and see­ing your­self. It’s about giv­ing your­self cred­it and not giv­ing your­self too much cred­it, and how no one real­ly knows what is going on inside a mar­riage, espe­cial­ly the two peo­ple inside it. It’s about how we talk about women and men, hus­bands and wives, and how the way we look at any sto­ry is always sus­pect — we must exam­ine the sto­ry­teller. Toby Fleish­man looks like he’s in trou­ble, but then again, the read­er is most­ly hear­ing from Toby. Rachel Fleish­man has dis­ap­peared — she’s prob­a­bly in trou­ble too.

Evie Saphire-Bern­stein is the pro­gram direc­tor of Jew­ish Book Coun­cil. She grad­u­at­ed from the Uni­ver­si­ty of Illi­nois at Chica­go with a B.A. in Eng­lish and a minor in Jew­ish Stud­ies. Before join­ing the Jew­ish Book Coun­cil team in 2015, she spent a year and a half work­ing with­in the Con­ser­v­a­tive Move­ment as the Net­work Liai­son for the Schechter Day School Net­work. She is a recent trans­plant to New York City, after liv­ing in Chica­go for most of her life. In her spare time, Evie is a writer and blogger.

Discussion Questions

The sto­ry begins in the mid­dle. Meet Toby Fleish­man, a forty-one-year-old suc­cess­ful physi­cian whose mar­riage just failed. He was faith­ful to his now ex-wife, Rachel, but today his phone is buzzing with women (some­thing he nev­er thought pos­si­ble). Incon­ve­nient­ly, Rachel drops his pre-ado­les­cent chil­dren off early…and then van­ish­es. No text, no calls, no trace, noth­ing. And we are trans­port­ed to where it all start­ed, to Toby’s junior year abroad in Israel where he meets three friends. A com­pli­cat­ed rela­tion­ship ensues and their shared expe­ri­ences, includ­ing a prophe­cy from an old woman in Jerusalem, influ­ences their futures in unex­pect­ed ways. It’s also about Rachel liv­ing the Amer­i­can Jew­ish dream, mar­ried to a respect­ed doc­tor with two chil­dren (a girl and a boy), a suc­cess­ful career and yet in the end it’s not enough, it’s nev­er enough. And she dis­ap­pears. The book exam­ines the diver­si­ty of the Amer­i­can Jew­ish expe­ri­ence. With rich char­ac­ters read­ers will find them­selves repeat­ed­ly say­ing I know that per­son.” Taffy Brodess­er-Akn­er brings the exquis­ite writ­ing her fans expect to her first nov­el. It’s a resound­ing suc­cess with wide appeal.