Taffy Brodesser-Akner, the author and showrunner of Fleishman Is in Trouble was around 40 when she noticed that many of her friends were getting divorced and downloading dating apps. Although married, Brodesser-Akner was fascinated by the dating revolution that seemed to have happened in the years since she’d been single.
“You could be lying in bed, watching TV and scrolling through potential partners, all of whom decided to show up at the same exact place, which is your phone,” she says. “It changed everything.”
Brodesser-Akner found that straight men on the dating apps seemed to be having “ridiculously wonderful times.” But her straight women friends weren’t so lucky: “Men their age were looking for somebody younger or thinner, or with fewer kids or with no kids,” she says.
Meanwhile, Brodesser-Akner had made a name for herself writing incisive celebrity profiles for publications like GQ and The New York Times, but she was having her own mid-life crisis. Living in the suburbs felt stifling, and she hadn’t accomplished what she wanted to creatively. Inspired by her own experiences and by her friends, she started working on a novel.
Fleishman Is in Trouble published in 2019, tells the story of Toby Fleishman, a 41-year-old divorced father of two who dives into the brave new world of internet dating. But at the beginning of his summer of sexual freedom, Fleishman’s estranged ex-wife disappears, leaving him to take care of their 9- and 11-year-old kids.
Now a limited FX/Hulu series, Fleishman Is in Trouble uses actors who became famous for playing teenagers to depict the drama of early middle-age crisis: Jesse Eisenberg (of The Social Network) plays Fleishman, Claire Danes (of My So Called Life) is his ex-wife, and Lizzy Caplan (of (Mean Girls) and Adam Brody (of The OC.) are his friends, Libby and Seth.
“All these people that we knew so well as very, very young people — it hits home for me so much. … This is a force you cannot fight,” she says. “We’re all going to get old.”
On wanting to write about the shock of mid-life and adulthood
I’ve always been into wondering what adulthood would be like. I didn’t realize that by the time you finally realize you’re an adult, there’s no “prime” of that. By the time I figured out how not to care if people liked me so much, or how to understand that I would like to play more basketball my knees started to hurt and I started not to be able to go out as much because my kids have homework. I was always very interested in adulthood. I had a fairly strict upbringing. And to me, I always had my eyes on the prize of freedom, which I think is why the freedom that goes away when you make these adult choices was such a shock to me.
On choosing to have Fleishman’s story be narrated by his friend Libby
I was having this crisis in the journalism I was writing. I write a lot of profiles, and it got to the point where I would spend enough time with my subjects who told me very personal things about their lives, and about their pasts, and about their marriages that ended, and about their children, and about their struggles in the world, and their gripes with the world, and sort of how it’s been for them since they took off. I would be enthralled and then towards the end, I would start to wonder — I worked at GQ and then at the time most of them were men – what would the women in their lives say? What would the other people in their lives say? And Fleishman comes out of this crisis of remembering that you don’t really ever know a story at all.
On similarities between herself and Fleishman’s friend Libby
In fiction, you’ve made it up, so everything is you. Everything, every person on the page is some aspect of you. But Libby, especially as rendered in the show by Lizzy Caplan, is cooler than I am. … But the things about her, she worked at a men’s magazine. She has a very devoted husband and two children, and she just feels lost in the world. I have all of those things except that I left the men’s magazine to go to The New York Times. … Where we diverge is that she, during the summer, needs some time to come and figure out what she wants to do. Whereas I went off to The New York Times and had a pretty good time, I just couldn’t figure out a way to convey how miserable I was in the suburbs and how the beginning of middle age hit me like a truck.
On two regrets she has from writing celebrity profiles over the years
I only regret two things: One, in that Mötley Crüe profile, they weren’t so kind to me that day. … I’m not here for revenge, but I think I was maybe hurt by it. It was one of my first few profiles, and I was just starting out, and I took a shot at one of the band members’ appearances. And I just feel like that is beneath me, beneath us. It did a lot to inform me about how I want to be in the world. And I don’t want to be someone who is funny at other people’s expense. It was a funny line, but it was at someone’s expense. .
The other thing I regret is that I once asked a recovering addict too many questions about addiction. … Again, I was starting out and an editor had given me questions to ask, and I was trying to be a good girl. … But I’m the one on the front lines, right? Like I’m the one. I can’t try to get my next job at the expense of this person, whose only sin in the world is that they have a publicity obligation and have to sit down with me. I’ve always regretted that. And I’ve always thought of reaching out to the person and saying something. And I don’t know why I haven’t. Maybe because I don’t even know if I did it as badly as I remember doing it. But I think about it all the time.
On some of the differences she experienced writing for women’s magazines vs. men’s magazines
When I was sent to do profiles for women’s magazines, very, very often — not all the time — … I would be given a list of questions to ask in the order that they should be asked. I was asked to ask women what their least favorite parts of their bodies were, until the point where I just stopped doing those kinds of interviews because I was doing well enough at other things. It felt so bad all the time to be going somewhere and writing down what a woman was eating. It felt like everything was wrong.
And women’s magazines, to me, always felt like the hold they had on the reader was that they were trying to control the reader: telling her how to eat, and how to flirt, and how to dress, and how to have sex. And even when they were trying to empower her, it was in these very specific ways. I was always told, when you write for a women’s magazine, “When you write for us, you have to write with the authoritative tone of voice that is the reader’s older sister or best friend who knows more than she does.” And I was a little allergic to that. …
When I started writing for a men’s magazine, it was just total freedom. It was: Write what you observe. There is no need to put in any of the stuff that seems boring or you don’t have to do any sort of data drop or include statistics or even justify why you’re writing the story. Like that was the greatest thing in the world. The idea that you could just write a story because the story happened or because you just thought of it, versus: we’re writing about Botox because we have these Botox advertisers. And also, make sure you say nice things about Botox. Those left me very, very cold.
Seth Kelley and Thea Chaloner produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Beth Novey adapted it for the web.