Taffy Brodesser-Akner's Double Trouble

When we meet Toby Fleishman, the forty-one-year-old New Yorker is newly single after a bitter divorce with his now truant ex-wife. (She dropped the kids off, then dropped from sight.) He's scrambling to meet his responsibilities as a doctor, while assuming all the caretaking of his children. He's also heavily distracted by his recent discovery of dating apps and casual hookups. And he doesn't quite grasp how he got to this place.

He has to learn a bit more about what went wrong in his marriage in the first place," says Taffy Brodesser-Akner, author of the 2019 bestseller Fleishman Is in Trouble, the basis for the limited series debuting on FX in November. (A rash of divorces among her friends, where the women were the high earners, prompted the book.) She served as showrunner and an executive producer of the series — which carries the same name as the novel — while also penning seven of the eight episodes.

It was something of a role reversal for Brodesser-Akner, who's known for the shrewdly observant celebrity profiles she crafts for publications like GQ and The New York Times Magazine. (Her article "How Goop Haters Made Gwyneth Paltrow's Company Worth $250 Million" caused tongues to wag coast-to-coast.)

But she had solid support: after convincing the author that her singular voice was critical to making the series work, executive producer Sarah Timberman flew in from L.A., Brodesser-Akner says, "to help me run this show that I was absolutely not qualified to do." (Other executive producers include Carl Beverly and Susannah Grant as well as directors Jonathan Dayton and Valerie Faris.)

Though she hadn't originally envisioned Jesse Eisenberg as Toby (in the novel, the character takes potshots at his short stature), Eisenberg hit the right tone. "He's incredibly versed in the sort of satire and irony required." And if the actor was a tad too tall, "I forgive him for it," she says, laughing. "There was not a day when he didn't break my heart or make me cry or make me laugh."

As far as corralling Claire Danes to play Rachel (Toby's successful talent agent wife, who happens to out-earn him) and Lizzy Caplan to portray Toby's college chum, Libby (a former magazine writer turned stay-at-home-mom), those characters are not initially front and center in the story.

Brodesser-Akner imagined that might be a dealbreaker. But "both had read the book and understood the gig." In fact, when Brodesser-Akner tried to layer in two extra scenes for Danes, the actress balked. "She said to me, 'You can't do this. This is not what the story is.'"

Besides, the women eventually get their say. It turns out, they have troubles too. And Fleishman really needs to listen.

This article originally appeared in emmy magazine issue #11, 2022, under the title, "When Couples Collide."