How ‘Fleishman Is in Trouble’ Turned a Writer’s Life Into Prestige TV – Rolling Stone

Taffy Brodesser Akner made a name for herself as an incisive, award-winning, frequently hilarious celebrity profiler, with viral features on the likes of Britney Spears and Gwyneth Paltrow. But on her odyssey from journalist to novelist to TV show creator, she was started to realize she wasn’t as good at her original job as she had assumed.

In 2019, Brodesser-Akner published Fleishman Is in Trouble, a seriocomic novel about middle-aged, newly-divorced New York doctor Toby Fleishman, who discovers that he is a hot sexual commodity on the apps, then finds his life spiraling when his ex-wife Rachel appears to ghost him and their kids. After FX bought the TV rights, she insisted on adapting the book herself, because “Every time some great writer was talking about adapting it, I became very jealous.”

But when Brodesser-Akner first had dinner with her cast — including Jesse Eisenberg as Toby, Claire Danes as Rachel, and Lizzy Caplan and Adam Brody as Toby’s old college friends Libby and Seth — she was shocked to find them being far more open and candid with her in a way that none of her interview subjects had ever been. “Nobody ever told me anything real,” she decided.

However artificial she now finds her reporting, Brodesser-Akner gets at something very real, and very creatively satisfying, with the show

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Full disclosure: Brodesser-Akner and I have become friendly in the years since the book was first published. But I have also watched plenty of shows made by or starring people I know without the real-life affection translating into similar feelings about the material. Brodesser-Akner spoke with

Rolling Stone

about the surprising things she learned from this career shift, getting Lizzy Caplan to play a version of herself, realizing that her children might see such a raunchy show created by her, and more.
Linda Kallerus/FX [producers] Prose and comic book writers who transition into screenwriting often talk about having to unlearn old habits. What was the biggest challenge of turning the book into scripts for eight episodes?

The efficiency you need in a TV show was brutal and cruel. The amount of darlings, you don’t kill them — they’re aborted in the uterus. I had
Sarah Timberman and Susannah Grant working very hard to help me see where the successful transition to visual television was. I thought, because I used a voiceover, you could just say it. The thing that was hardest, and most tragic, for me to learn, is that the visuals do it better. I was like, “What about my words? What about my turns of phrases?” And that was nothing compared to what happened on the first day that I saw actors. All this time I spent writing profiles, and I never understood the way an actor turns this thing on when it’s yours. I can’t believe I missed it! That was the story. The story was, you could do that, and I was asking about failed marriages!

You got all this acclaim for those profiles, but now you’re working alongside the kinds of people you used to interview. What was that like?

I think the thing that I prided myself on was not pretending that I was getting to know people intimately. I grappled not with who they were but with who they were presenting themselves as, because why would any of these people want to be intimate with me? But I guess I also secretly had some kind of vanity that I got people to talk to me. I was wrong.
The first time I had dinner with our actors, the way they just started talking to each other, and to me, I was in stunned silence. I was like, “Oh my god. Nobody ever spoke to me this way.” What an idiot I was! I would always think that, after the third meeting, I wore them down. And no — I never wore anybody down. Nobody ever told me anything real. The thing that made those stories successful was that I didn’t pretend that they were telling me something real. All I ever wanted to know was why they were telling me what they were telling me, and spend months with them, and have them have their good days and their bad days, and their vulnerable days, and their annoyed days. I couldn’t believe how real everybody was in front of me. Like, I would want to say to them, “Don’t you know that I’m a profile writer?” But I wasn’t for them. I felt like I was being let into a secret world where everyone is human. And I’m not as good at my job as I thought.

If you ever do go back to journalism, is this going to change how you do that?

It will change it because there’s part of me that wonders if I now identify with my captors a little too much. And also, if an agent or a publicist would think of me as too friendly. That’s also not fair, for someone to sit down with me not knowing that I’m doing this other job. So I don’t know if I can do that again. But I do know that I will definitely have feelings about the walls that go up. Which they are entitled to, and are healthy, and are good. I’m still a real person. I believed that these people were never my friends. Bad profiles are written by people who get charmed into thinking they’re friends. I was like, “I don’t want to talk to these people ever again. I don’t ever want to watch another movie by them. I want to forget that they existed.”
But I would ask more questions about what makes you into the kind of person who wants to do this. Because that is also fascinating to me. I did not have any nightmare Method-y stories on my set. Everyone was like a totally normal person, which was shocking to me. So I have more questions about how you do this or why you do this. And I’m not sure those will be interesting to a reader. I’ve always asked questions that were interesting to me, but I don’t know if the things that are interesting to me now are still interesting to anyone else.

What was it like watching actors like Jesse and Lizzy perform these words that you wrote?

They each brought a level of complete insanity to my experience. Watching Jesse, who is a movie star, take on this character, and make choices about him that I hadn’t written, but were good and valid? A weird thing that happens these days is that your algorithms are all reading your email. So on every television I have on this place, all I have on the screen being fed to me are Jesse, Claire, Adam Brody, and Lizzy Caplan. My algorithm just thinks I’m a superfan because I email about them all the time. So my kids end up watching these movies, and I walk through the living room seeing them. What is insane to me, and this sounds elementary, but it never occurred to me that he created a whole new Jesse Eisenberg for this character. You can’t find his tics or his mannerisms in this show in any of his movies. The minute I saw that, you know what it was like? This is so embarrassing to admit, but it was like a fantasy. I’d be standing there in the village looking at the screen. And up til the last day, I could not process that I’d written a book and Jesse Eisenberg was playing this character. Claire Danes was dazzling in her ability to be having a conversation like a normal person, and someone would say action, and she was different. She was a different thing. You’d watch it in front of you, and you couldn’t believe it. Lizzy, I had this strange relationship, because what if you got a character who was a surrogate of yourself, and it was Lizzy Caplan? And Adam Brody, he brought this naturalism. All of them were doing this as children, successfully. So they are so cool about it. I put so much of my heart and my childhood and my vulnerability into this book and into these scripts. And the thing I never expected was that watching these people say things that were my thoughts would make my thoughts more forgivable to me. It was like exposure therapy for what a nightmare I think I am:

When they say it, they seem, like, great! Maybe I’m not terrible! It would adjust my self-loathing a little bit. I didn’t expect that.There’s this famous Jason Alexander line where he said that in the early days of
His field , he didn’t know how to play George until he realized the character was just Larry David, and he would watch Larry and figure out how to channel that. Did Lizzy do any of that with you?She read the book, and she had a relationship with Sarah Timberman, because Sarah had done [as] Masters of Sex

. Lizzy expressed some concern at first. She wanted to know how to capture my essence. And she saw this watch I was wearing. It’s a Casio calculator watch. And I said, “I’m going to buy you one. Because it’s like $60.” I bought one, and the props department bought one, and she put it on, and I said, “When I wear it, I’m a giant nerd. And when she wears it, she’s the coolest person in the world.” The difference between us is, she’s saying all the things to me, but when she does it, she’s cool. Where

I’m not cool. So we didn’t have these talks about it. She understood it, and then she made it hers.

Sometimes, I would look and say, “Is it working for her to be this cool?” And the answer was always a resounding, “Yes. It’s better.” Her interpretation of this makes more sense in the end. In the end, you can say, “Why weren’t you happy in the suburbs? You kind of seemed like you belong there.” But Lizzy, you look at her and you get it. It’s like the transition to visual storytelling. Of course Lizzy Caplan doesn’t belong in the suburbs. I do!
Linda Kallerus/FX The characters on this show are explicitly Jewish in a way TV can sometimes be reluctant to talk about. Toby meets his friends on a college trip to Israel, his daughter is studying for her bat mitzvah, and we learn that Rachel falls more deeply for him after she has a traditional Friday night dinner with his family. How important was it for you to maintain the level of Jewishness from the book into this show? I don’t necessarily think of it Fleishman as Jewish. It’s incidentally Jewish. But I have a theory that the goal of all Jewish art is that we are constantly trying to prove that we are real Americans. And the casting of Gentiles as Jews is a proof — like, “Look! Look at Mrs Maisel!” They don’t even know the name is pronounced “My-zell.” But that said, I saw

Scenes from a Marriage.
I grew up in an Orthodox community, and you could line up Oscar Isaac doing that Jewish guy with any Jew I ever met, and you would not be able to discern. But I think that that happens because how could you ever deprive yourself of the opportunity to have movie stars playing your people? And there aren’t that many Jewish movie stars. But it is about still proving ourselves as Americans. The book is very explicit about all the sex that Toby is having, and being offered, while he’s on the apps. The show is very explicit about it, too. How did you figure out what worked on the screen in terms of what to show and what to talk about? It was a really hard decision. I’m very comfortable with words. And then when our directors showed us a manifestation of what the one of the app sequence would look like. I was shocked, and I needed a few days. Then I decided, it’s like talking the talk versus walking the walk:

You did this, sister. You wrote this. This is the vision of the show.

Which is a very delightedly shocked woman telling the story of her friend’s foray into app-assisted sex. Half of it is her imagination and the embellishment of it. And half of it is, well, that’s what sex looks like. You can’t tiptoe around it. [Note: After this interview, Brodesser-Akner changed her mind on that last point. “The night before the premiere, I decided they should stay. They should know who their mother is. I also felt that their friends would be able to see it, and I didn’t want them to be exposed to it [through them]trending

There was nothing more shocking to me than finding out that the things you write, someone is going to make them into pictures, and you will have nowhere to hide. I could say to my mother, “You know, it’s not that dirty a book.” But I cannot say to my children, “It’s not that dirty a show.” My children are going to have to leave the premiere before the screening starts. I can’t allow them to think that I know about those things. Everyone has the right to think that their parents don’t know about these things. .”] The first two episodes of

Fleishman Is In Troublepremiere November 17 on Hulu, with additional episodes streaming weekly.

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