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Middle age 'is a force you cannot fight,' warns 'Fleishman Is in Trouble' author

The series "Fleishman Is In Trouble" was adapted by our guest, Taffy Brodesser-Akner, from her novel of the same name. The complete season is now streaming on Hulu. Brodesser-Akner is also known for her celebrity profiles in GQ and The New York Times, where she's a staff writer for the magazine.


Other segments from the episode on January 11, 2023

Fresh Air with Terry Gross, January 11, 2023: Interview with Taffy Brodesser-Akner; Interview with Chloe Sorvino



This is FRESH AIR. I'm Terry Gross. The series "Fleishman Is In Trouble" was adapted by our guest, Taffy Brodesser-Akner, from her novel of the same name. The complete season is now streaming on Hulu. Brodesser-Akner is also known for her celebrity profiles in GQ and The New York Times, where she's a staff writer for the magazine. She spoke with our guest interviewer, Tonya Mosley, host of the podcast Truth be Told.

TONYA MOSLEY, BYLINE: Taffy Brodesser-Akner's midlife crisis happened earlier than most. At 33, with a 1-year-old baby in tow, Taffy realized she wasn't experiencing the wild, professional success she'd imagined for herself, like her other classmates from film school. Taffy got to work becoming a self-described idea machine, writing articles out of her insatiable desire to be a storyteller. Now, more than a decade later, she's known for her celebrity profiles for GQ, ESPN The Magazine, The New York Times and others. In her 40s, she wrote and published her first novel, "Fleishman Is In Trouble," which she turned into a limited FX series now streaming on Hulu.

"Fleishman Is In Trouble" centers around a 41-year-old divorced doctor named Toby Fleishman, played by Jesse Eisenberg, who post-divorce dives into the brave new world of dating on apps. But at the start of his summer of sexual freedom, Toby's ex-wife, Rachel, played by Claire Danes, disappears, leaving him with their 9- and 11-year-old kids. While Toby Fleishman balances work and single parenting, he begins hanging out with Libby and Seth, two old college friends played by Lizzy Caplan and Adam Brody. Here they are inside of Toby's apartment, talking over takeout about the realities of marriage and divorce. Jesse Eisenberg's character speaks first.


JESSE EISENBERG: (As Toby Fleishman) Divorce is like that old Othello game, you know? You start your marriage with all the disks white, right? And then there are some black disks here and there along the way. You know, you fight, but ultimately, you laugh, and it's fine because the board is still mostly white, right? But then something happens, and the marriage falls apart, and suddenly, the entire board is black.

ADAM BRODY: (As Seth Morris) Is that how you play Othello?

LIZZY CAPLAN: (As Libby Epstein) They should probably change the name Othello, you know?

EISENBERG: (As Toby Fleishman) Yeah. So now even the good memories are, like, tinged with darkness. You know, they're tainted like they were rotten from the start.

CAPLAN: (As Libby Epstein) Not all of them.

EISENBERG: (As Toby Fleishman) Yes, man, all of them, OK? Now you look back on all those memories, like the fight you had on the honeymoon, the way you couldn't agree on, like, a name for your child, and suddenly, they're no longer innocuous fights anymore. Now they're foreshadowing. I think when we get married, we really have no way to fully understand what forever means.

MOSLEY: Taffy Brodesser-Akner is the writer, showrunner and executive producer of the limited series adaptation of "Fleishman Is In Trouble" and a staff writer with The New York Times. She's won many awards for her profiles, including the New York Press Club Award and the Mirror Award.

Taffy, welcome to FRESH AIR, and congratulations on the success of the series.

TAFFY BRODESSER-AKNER: Tonya, thank you so much. What a kind introduction.

MOSLEY: When you were around 40, you noticed that so many of your friends were getting divorced, and all of them were on dating apps. Same; I saw that, too. And like you, one of my favorite things is to have my single friends show me their dating apps. What did you find that then became the inspiration for you to write an entire storyline and book?

BRODESSER-AKNER: I mean, I just thought that the way people are dating now is such a revolution over the way it's always been. You know, you get dressed up. You go out. You try not to look too needy. You try not to look too desperate. You try to forget that, you know, your college roommate is prettier than you. And you try to figure out the right place to go where you will find somebody that is somehow waiting for you, that you've been told in romantic comedies is waiting for you.

And here this revolution came and 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, and it changed everything. Or I thought it changed everything. In the end, I believe in heterosexual dating men are still very much in charge, but mostly what I saw was how I would have liked to have spent my time back then instead of, you know, showing up in my human body with makeup on.

MOSLEY: It's rare for a novelist to adapt their own work and have creative control over production for an actual show. Had that always been an aspiration of yours?

BRODESSER-AKNER: It had never been an aspiration of mine. It wasn't even an aspiration of mine in doing this. But luckily - I think maybe perhaps when you write about middle age and one of your characters is an agent, a lot of people in Hollywood were interested in this. And I thought I would sell it and continue working at The Times. But every time I spoke to producers or writers on the phone who wanted to adapt it, I would feel a sort of jealousy. But I was very focused and I had this great job. I love working at The New York Times. So I continued talking to people. And then one day, I spoke to Sarah Timberman and Susannah Grant, who ultimately became my producing partners on this.

MOSLEY: They're well-known producers in the industry. Yes.

BRODESSER-AKNER: Well - legends of the industry, the most wonderful people in the world. And the first thing they said to me was, well, you would have to write this yourself. It's in your voice. No one else could do it. And when you say I had total control, actually what I had were these people who are beloved and trusted and, again, legends in this industry. And I believe deep down it's they who had the control, and they gave it to me. Their control consisted of saying to me, here's how you do this, and then to stand back and let me try it.

MOSLEY: Part of the confidence that they had in you was also because this is not a straight-ahead story. It's - spoiler alert - "Fleishman Is In Trouble" plays with perspective because, on the surface, it's about a 41-year-old divorced doctor. But by the end, we are aware that he was the vehicle to tell a much bigger story about the midlife crises of the women in his life, his ex-wife, Rachel and his friend - his college friend, Libby. Why did you tell the story this way - initially, through this male character of Toby?

BRODESSER-AKNER: There are two reasons. One is good, and one is sad. And the first reason is because I was having this crisis in the journalism I was writing. As you said, 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. And I would always sit and think toward the end. I would be enthralled. And then toward the end, I would start to wonder, what would the people that this person is mentioning - and most - and I worked at GQ and then at the Times. 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.

And the second reason is because I grew up with this brand of book, like a "Portnoy's Complaint" or an "American Pastoral" or "Rabbit, Run" - like a Philip Roth, John Updike, male-point-of-view story that I always loved. Those were my favorite stories. And what I found when my friends came to me and showed me their phones were that the men were having these ridiculously wonderful times on these phones and with their apps and dating. And for the women, it was relatively dismal.

It was that the men their age were looking for somebody younger or thinner or with fewer kids or with no kids. And it got to the point where I would - I mean, I would look at - I have a friend who came over to my house once to change for a date because she had teenage daughters, and she didn't want them to know she was going on this date. And I said, show me your phone. I'm writing this book. Show me your phone. And she showed me her phone. And it was this guy. His profile description said something to the effect of, you know, my ex-wife was a psychopath. And if you're into playing games, please, swipe away from me. But if you're a normal person - you know?

MOSLEY: (Laughter) Yeah.

BRODESSER-AKNER: And I was like - and I said to her, what about this was interesting for you? And she said, it was the best of the crop in weeks.

MOSLEY: The best? Right.



BRODESSER-AKNER: It's really amazing. So when I wrote the book, it seemed like just a more fun way of entering the story, to tell the story of a man.

MOSLEY: If you're just joining us, I'm talking with writer Taffy Brodesser-Akner. She's the writer, showrunner and executive producer of the FX on Hulu limited series adaptation of "Fleishman Is In Trouble" and a staff writer with The New York Times. We'll be right back. This is FRESH AIR.


MOSLEY: This is FRESH AIR. I'm Tonya Mosley, talking with Taffy Brodesser-Akner. She's the writer, showrunner and executive producer of the FX on Hulu limited series "Fleishman Is In Trouble." It's an adaptation of her bestselling novel by the same name. Taffy is also known for her award-winning celebrity profiles of stars like Nicki Minaj, Don Lemon and Tom Hanks for several publications, including GQ magazine. The narrator is Toby's college friend, Libby, which is an interesting way to tell this story. She's a former staff writer for a men's magazine who is now a stay-at-home mom living in New Jersey. She's the character that is most like you. But I've also heard you say she's not entirely you. What are the parts that are you?

BRODESSER-AKNER: I mean, it's an interesting question because in fiction, you know, you've made it up. So everything is you, right? 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's just feeling 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.

And it just became - for the plot of the story, 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 start of middle age hit me like a truck. There was no way to really do that and also, you know, have this really fun job at The New York Times where you're, you know, being sent to Budapest to interview Antonio Banderas (laughter).

MOSLEY: Right. So the divergence is she leaves the men's magazine. And she says, I'm going to write a book. But two years later, she has not done that. So her decision to quit the magazine to write a novel - after, she realizes she'll never be seen as that genius star writer, that title of a genius writer is almost always given to men. I want to play a scene. It's two years after Libby has decided to quit. And she's lost, as you said. Here she is reflecting after going on vacation with her family.


CAPLAN: (As Libby Epstein) But now it's two years later. I haven't once even opened a blank page, made an attempt. And here's the secret of my vacation - that while we were on the rides and standing in lines and taking pictures, I wasn't really with my family. I wasn't in Florida. I wasn't on an airplane. I wasn't at a themed restaurant begging a hostess for a reservation everyone in the world knew to make weeks before, but not me. I wasn't even at home, unloading the car.

JOSH RADNOR: (As Adam Epstein) I don't know what to do with you.

CAPLAN: (As Libby Epstein) I was with Toby.

MOSLEY: Taffy. OK, first of all, the soundtrack.

BRODESSER-AKNER: That's Caroline Shaw.

MOSLEY: Caroline Shaw. Yes.

BRODESSER-AKNER: And that is my absolute favorite track that gets sort of distorted, like, rendered and then distorted and then made orchestral along the way. It's called "Ring Of Copper." And it's this - you know, my husband describes it as a music box with - you know, that's charred and burnt with bent strings. It's just this - it's the beautiful sound of the longing of my soul that Caroline, who is a genius, was able to execute so, so beautifully.

MOSLEY: Well, Taffy, that soundtrack that Caroline Shaw produced for the series is enrapturing. But the thoughts that Libby expresses in this scene are thoughts that many women have but are never really expressed. And I find it to be so honest. Was it easy for you to get to that place, to say something that is unspoken, that maybe mothers aren't with their children mentally when they're in these other places? They're thinking about the other parts of themselves.

BRODESSER-AKNER: I found it easy because I had been doing it since the minute my children were born. I have been running around and grabbing people by the lapels and saying, like, what are you supposed to be thinking about? What is the right - in Hebrew, the word is kavanah. It means intention. Like, what are you supposed to be thinking about while you're taking care of your children? And are you - is it seditious to not be thinking about your children when you're with your children, especially when they're very, very young?

But that's what these thoughts are. They're a kind of sedition, but they're also a kind of freedom that nobody gets the totality of your brain. And Libby, who has had this summer where she is spending time in the city again, where she used to live, and she is with friends who knew her when she was young and when she was all potential - she's suddenly sent to Disneyland. And I don't know anybody who does not ask themselves a lot of hard questions whence - when on a Disneyland vacation, or on a Disney World vacation, where you're stuck with nothing other than the family that you've created - and, of course, an incredibly privileged position to go to Disney World - but also to ask yourself, is this what I thought it would - what happened to the version of me that was a few days ago sitting in the park like I was young again or the version of me that was supposed to be somewhere else by now? And that is what's on her mind.

MOSLEY: How intentional was it to cast middle-age actors we first knew as teenagers?

BRODESSER-AKNER: It was so intentional. It was - you know, there was this idea that these actors were too young to play these roles. I mean, Jesse Eisenberg, when we started talking about the adaptation, was only 36 years old. Luckily - and I mean that facetiously - the pandemic came along, and by the time...

MOSLEY: He got older?

BRODESSER-AKNER: 38 - so we were able to rationalize that. But we had these choices. Did we want to cast people who were older who we could then look at as in a more authentic crisis of middle age? But the point of the book and the show are the beginnings of those crises. And also, this allowed us to have them play themselves in flashbacks. But most of all, and your question hits it exactly correctly, if I don't, as a 40-year-old, yet understand what is happening to me in my life, the idea that Jesse Eisenberg - yes, from "The Squid And The Whale," yes, from "The Social Network" - that it's happening to him, too, that it's happening to Claire Danes from "My So-Called Life," that it's happening to - oh, my gosh - to Adam Brody, to Lizzy Caplan, to Josh Radnor - all these people that we knew so well as very, very young people. It hits home for me so much to say, oh, my God, this is a force you cannot fight - if you're lucky. If you're lucky and you get to live, this is a force that you won't be able to fight. We're all going to get old.

MOSLEY: We're all going to get old. Actor Lizzy Caplan, who you mentioned, who plays the role of Libby - she said something to the effect of, it's a dream to have aged into this type of material because it's why she became an actress. And she mentioned Adam Brody and how he should have aged into these incredible cerebral parts. But there's no material to support it. And when I read that, that really brought home for me a deepening of why I love this story so much. We don't see this kind of character excavation of Gen X often.

BRODESSER-AKNER: I've always been into wondering what adulthood would be like. I did not 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 to not care if people liked me so much or how to understand that - you know, 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. So those are the - 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.

GROSS: We're listening to the interview our guest interviewer Tonya Mosley recorded with Taffy Brodesser-Akner, the creator and showrunner of the series "Fleishman Is In Trouble," which is streaming on Hulu. Brodesser-Akner adapted the series from her bestselling novel of the same name. We'll hear more of their interview after a break. And we'll talk with Chloe Sorvino, author of "Raw Deal," about why the meat industry is damaging the environment and contributing to global warming. She'll tell us about some promising alternatives to meat. I'm Terry Gross. And this is FRESH AIR.


GROSS: This is FRESH AIR. I am Terry Gross. Let's get back to the conversation our guest interviewer, Tonya Mosley, recorded with Taffy Brodesser-Akner - creator, writer and showrunner of the FX series "Fleishman Is In Trouble." It's now streaming on Hulu. Brodesser-Akner adapted the series from her own bestselling novel of the same name. She's a staff writer at The New York Times Magazine and is known for her celebrity profiles.

MOSLEY: Taffy, as we've been mentioning, you started as a celebrity profile writer in this space with GQ and The New York Times and many of - other publications. Well, most of your writing - you always exist. So the fourth wall is always broken, and your voice and tone are almost always about tearing down kind of the artifice of a celebrity. And an example is your profile on Gwyneth Paltrow and Goop for The New York Times. People either loved it or hated it. Maybe journalism purists hated it. Why do you think this style of writing - maybe why people are so taken by it, have such strong emotions about it - why this type of writing can be polarizing?

BRODESSER-AKNER: You know, it's funny. I have two thoughts on that. One of them is that to pretend that there is no person writing this story is its own dishonesty. And I don't know. In terms of it being polarizing, this was what the theory I came up with along the way on Gwyneth was, that the reason people hated her so much was because she was this sort of reflection back to us about what our deficits were. And one of our deficits, in general, is exquisite beauty and thinness and wealth. And if I think about the people who perpetuated the notion that we - whoever we is - hated her, it was journalists.

Because I got to tell you, from experience - and I think I put that into the story - it is very hard to be a regular person in the world who sometimes eats pizza and who sometimes doesn't exercise for two weeks and who is concerned about paying for camp. And then, you have to encounter Gwyneth, who has become so shiny in all of our eyes that we can't even see either her flaws or her problems. It's a very unique position to be in, but I do think journalists perpetuated it.

MOSLEY: I've heard you mention that you regret it, some of the things that you've written. And one of them was Motley Crue, a profile on Motley Crue, because it was perceived as mean. What are some of the other profiles or profile that you regret doing?

BRODESSER-AKNER: You know, I only regret two things. One, in that Motley Crue profile, they weren't so kind to me that day, which doesn't mean - you know, I'm not here for revenge, but I think I was maybe hurt by it. And I was - 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, that no - you know, 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.

And the other thing I regret is something I don't - I rarely talk about it because I - when you talk about it, it's to implicate somebody. But I can say vaguely enough that I once asked a recovering addict too many questions about addiction. And afterward, I left, and I sort of didn't realize that I was - 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 has 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 know - I don't even know if I did it as badly as I remember doing it. But I think about it all the time.

MOSLEY: Taffy, you're from Brooklyn. You lived in two neighborhoods in Brooklyn - Flatbush and Canarsie. How would you describe them?

BRODESSER-AKNER: I would describe Flatbush and Canarsie as, when I was growing up, hard places to be from. Like, you know, Canarsie remains Canarsie from what I understand. It's hard to get to, so I never drive through it though sometimes I think I should. Flatbush, I somehow missed the - I was in the generation in between the romantic stickball Flatbush and the artisan cheese-making Flatbush of now. It just felt like either a way station or a place of - sometimes of hopelessness because of the lack of money that people had, the sort of many ethnicity wars that were always going on in the neighborhoods that I lived in.


BRODESSER-AKNER: It was not a fun place.

MOSLEY: As you mentioned, you were raised in an Orthodox Jewish family. How much of your family's history was part of your understanding of yourself growing up?

BRODESSER-AKNER: That's such an interesting question. I felt that my family's decision to become religious when I was 12, which is what happened - we were generally unaffiliated Jews. And then, when my mother - when I was 12, my mother decided to become very orthodox, and my sisters followed her. And I always felt like it's what made me into a journalist - the idea that for the remaining, you know, six years that I was home - there were these people that I love dearly, that I'm - that are still the closest people in the world to me. And I was baffled, completely baffled by their decision. I think I'm still equally as baffled, but I have a great amount of respect for who they are and how they live. And I guess the way it formed me was that it made me into someone who understood that you could hold both of those things in your hands.

MOSLEY: What made your family decide to become Orthodox Jewish?

BRODESSER-AKNER: When we moved to Brooklyn from Long Island, which is where we lived briefly while my parents were married. My mother was very shocked at the crassness of the culture, you know, fifth graders wearing eyeliner and short shorts. And she was always very conservative. And she felt that sending us to Jewish schools would help slow down the culture. And slowly, we came home from those schools saying, hey, how come everyone else keeps kosher and we don't? How come everyone else lights Shabbat candles and we don't? And my mother started participating more and more in that and then, one day, had a revelation that this is - that it was the people who were participating in religion in a more complete way that were somehow avoiding the pitfalls of the culture, which to her were drug use and premarital sex and unwanted pregnancies. And those were her priorities.

MOSLEY: I'm just curious. What was it like to write about divorce with two kids while being in a marriage with two kids?

BRODESSER-AKNER: It's very, very interesting. And I was very self-conscious about it. And I was always worried that that question would come to me and I wouldn't know how to answer it because I didn't know the answer to it - because I did know that everyone else I knew, their first novel was a coming-of-age novel. And what did it mean about me that I was so drawn to this subject matter? And I would say in my head, like, you know, I'm a journalist. I - this is what's interesting to me right now. And I'm very comfortable in saying that. But when I was at a reading and somebody asked me that - and my husband was there. And I finally said, I don't know. We should just ask him what he thinks about this. And he gave the best answer I've ever heard. And it's the truest.

MOSLEY: What did he say? Yeah.

BRODESSER-AKNER: Though, it didn't occur to me then, he said, she's obsessed with divorce. Her parents are divorced. Her sisters, some of them are divorced. Like, everyone around her has always gotten a divorce. And that's the answer I think I like the best. The idea that once you get married, your marriage becomes - because it's two people, becomes this sort of closed box. And you never really know if you're doing it right. But what happened was, when all those people started coming to me and telling me that they were getting divorced, all I could think of was that I was at their weddings. And they were happy on their wedding days, as happy as I was on mine. And what is it that I could do?

I felt that my parents' divorce was a catastrophic thing in my life. I can look at it now as a thing that has - like, that had the most long-term damage in my life to me and to my sisters, I think, and - though I won't speak for them. And I think - I don't know. Maybe it behooves us to examine these things a little more instead of pretending that these questions aren't on our minds. If these people could get divorced, it could happen to me. And I would like to do some preventative work. I would like to see it coming because I think that there are so many factors.

MOSLEY: Taffy Brodesser-Akner, thank you so much for this conversation.

BRODESSER-AKNER: Tonya, thank you so much for having me on. It's been wonderful.

GROSS: Taffy Brodesser-Akner is the creator, writer and showrunner of the FX series "Fleishman Is In Trouble." She spoke with our guest interviewer, Tonya Mosley, host of the podcast "Truth Be Told". "Fleishman Is In Trouble" is now streaming on Hulu. After we take a short break, Forbes staff writer Chloe Sorvino will talk about her new book, "Raw Deal," which investigates how the meat industry is damaging the environment and contributing to global warming. She'll tell us about promising meat substitutes that might reduce meat consumption and slow climate change. This is FRESH AIR.


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