Taffy Brodesser-Akner shines a light into the darkness of dysfunctional marriage and divorce in Fleishman Is in Trouble. Set in the world of Manhattan’s social climbing thirtysomethings, we meet Toby Fleishman first. He’s experiencing the unstable world of newly divorced parenthood. While he works as a hepatologist (that’s a liver specialist), his obsession with dating apps and the women he finds there is overwhelming. And yet, he’s a parent with 50/50 custody of two kids. Mostly Toby is an amateur juggler dropping balls and eliciting audience groans.

Toby and his soon-to-be-ex-wife Rachel have an uneasy détente around the kids and their schedules. It’s summer and that complicates things, with day camp and trips to the house in the Hamptons on the schedule. And then all of a sudden, Rachel drops the ball by virtually disappearing from sight. First, she’s a day late to pick up the kids, then it extends to a week, and so on. Toby does his best to manage, which includes a lot of personal days off from work, where he’s also managing a complicated case of rare liver disease. 

Around this time, Toby’s also reconnecting with two friends from college. Elizabeth (or Libby) is a writer who’s now a stay-at-home mom in the suburbs. Seth is still the same party guy and now a hard-charging finance professional. They do their best to keep Toby moored to some kind of reality, albeit based in shared history rather than current events.

My conclusions

Brodesser-Akner captures the feelings and realities of shared parenting gone horribly wrong. She develops Toby from a horny divorced dude with kids to a full-time dad conflicted about love, sex, and kids. At the same time, she uses a third-person narrative for his sections. That keeps him at arm’s length and made him less likable for me. Fair warning—Toby is really a horny dude. Be prepared for plenty of descriptive sexting and hookups.

I also appreciate how Brodesser-Akner builds the other character’s stories, whether it’s Toby’s kids, his friends, or Rachel. The kids function to move the story forward. The friends show where Toby came from. And as we learn more and more about Rachel, the arc of this story becomes clear.

Along the way, Brodesser-Akner discusses marriage and divorce, as well as identity. For me, this book proves once again that you never know a relationship completely unless you are in it. Looking from the outside, that couple next door seems perfect. But what you don’t know is the shout-whispered fights they have in the kitchen while company’s at the dinner table. Or how their oldest child’s birth really happened. 

This is also a quintessential Manhattan story, with lots of common locations and aspects of the city. It’s about the “middle class” up-and-comers, who didn’t inherit money and try to claw their way up the social stratum. But mostly it’s a family story that could’ve happened in any city. A marriage gone wrong and people just struggling to keep their heads above water.

I recommend if you want to dive into a book about edgy and uncomfortable twenty-first century relationships.

Pair with something about sex from a woman’s point of view, like Three Women by Lisa Taddeo or Living an Orgasmic Life by Xanet Pailet.