How do you follow a novel like Fleishman Is in Trouble? If Taffy Brodesser-Akner knew what people loved so much about her debut she would have replicated it, she says. The story of a newly divorced hepatologist discovering the joys of dating apps while trying to look after his two kids when his ex-wife goes missing on a yoga retreat, Fleishman Is in Trouble was one of the smartest, funniest novels of recent years. It was made into a hit TV series with a starry cast, for which Brodesser-Akner wrote the screenplay. But writing her second novel almost drove her “insane”. Long Island Compromise might be described as a Jewish take on The Corrections (Brodesser-Akner has read Jonathan Franzen’s 2001 novel four times); a whopping family saga about money and the American Dream, following three generations of the Fletcher family as they find, and then lose, their fortune. A TV version is already under way. “Writing for me is not generally hard,” Brodesser-Akner admits, “and every sentence in this book was a hard one.”
Before Fleishman, Brodesser-Akner had already made a name for herself as a New York Times profile writer, with a string of high-profile celebrity interviews including Britney Spears, Nicki Minaj (who fell asleep) and Gwyneth Paltrow, who she practically moved in with for a while. While she never lets her subjects off the hook, she brings to her journalism the same understanding of human absurdity and vanity that makes Fleishman so appealing. In 2018 she went to Santa Cruz to interview Franzen : “His sentences, wow!” she says now. “You don’t really get who he is unless you’re sitting around with him.” Her description of him not so much sitting on a couch but dripping off it, “like a Dali painting”, has been imprinted on my memory. That evening she wrote the final pages of Fleishman in her hotel room. “Bad profiles are written by people who get charmed into thinking they’re friends,” she has said, which is a pity because I would really like to be her friend.
Dressed all in black with DM-style boots, 48-year-old Brodesser-Akner looks and sounds uncannily similar to actor Lizzy Caplan, who plays Libby, the narrator and former magazine writer, in the TV version of Fleishman. We are sitting outside a converted railway station restaurant in King’s Cross, the inside being far too noisy (she knows all about dictaphone anxiety), next to a group of mothers and babies. She hunches – or “leans into” as she might say – her herbal tea, with the haunted posture of an ex-smoker. Or maybe she is just cold. It is still noisy. And raining. Paltrow’s kitchen it is not.
“I don’t miss it ever, do you?” she says of the mums trying to breastfeed while maintaining a conversation. As fans of the novel will know, Fleishman Is in Trouble turns out to be as much about the frustrations and loneliness of motherhood as it is about the antics of its eponymous hero. “When I had babies I wondered if something was wrong with me,” she says. “People would come over and say, ‘Oh, it goes so fast.’ And I’d say, ‘Really?’ Because it doesn’t feel like it. I wish anyone had said, ‘You look miserable. But just you wait!’ Now I have teenagers and they are so fun.”
She wrote the first 70 pages of Long Island Compromise, inspired by the real-life kidnapping of a wealthy Jewish businessman in Long Island in 1974, before she even started Fleishman. But she sent it to her then agent, who wasn’t keen, so she put it aside thinking maybe she should stick to the day job. Fleishman started life as a feature idea in 2016, but was turned down by GQ because dating apps were old news, apparently. So she carried on writing as if it were a regular profile – but of someone she was making up. Then her agent rejected that too. “I realised that maybe she just didn’t like my stuff. So I broke up with her and found my new agent, who liked both.” The day after she sent back the final edits on Fleishman, she reopened Long Island Compromise.
Ever the magazine writer, Fleishman was written partly out of her despair at the misogyny that kept Hillary Clinton out of the White House, and Long Island Compromise, although begun long before the outbreak of the Israel-Gaza conflict in 2023, was completed in a world becoming increasingly precarious on all fronts.
When she began both novels, nearly a decade ago, she was experiencing a “peak moment of anxiety”. She and her husband, also a journalist, Claude (he’s the Brodesser bit) had just returned to New York after a stint in LA, and paying rent and school fees on their freelance incomes was a worry. “I was working through some feeling about the state of wealth and the state of privilege,” she says. She wanted to write about privilege in the old-fashioned sense of immunity, how wealth buys peace of mind or “a lack of terror”. Having grown up without much money, she had been left with the question: “Was I better off for being someone who had figured out how to survive on my own? Or, as I sort of suspected, would it have been easier never to have to worry about my survival? I don’t know if I will ever not feel the wolf at the door.”
Long Island Compromise is all about wealth, and the wolf at the door. Immigrants from Europe during the second world war, the Fletchers build their empire on polystyrene – a neat metaphor for America, relatively new, virgin white and designed for keeping things safe. But polystyrene snaps easily and is impossible to put back together: and so it is after Carl, the second-generation Fletcher to take over the factory, is kidnapped one day, in the “preternaturally safe” Long Island suburb of Mount Rock, a promised land of McMansions, nose jobs and middle-class envy. The real kidnapping of Jack Teich on which it was based became famous because the ransom was the largest ever paid in the US. Brodesser-Akner wanted to write about a trauma that happened on American soil. “Growing up I read so many novels where the inherited trauma is the Holocaust. But so much else has happened in the interim,” she says. “I think you inherit a point of view more than anything, the fear that we might be victims at any point.”
The novel explores the idea of the American Dream as a “dream of safety in capitalist society that comes in the form of money as protection,” she explains. And the Jewish American Dream – only really different from the American one if you don’t think Jews are Americans, she points out – “is safety in a country that promised protections and freedom of religion and freedom from persecution. I don’t know if we’re still there.”
Set for the most part 40 years after the kidnapping, the novel follows the lives of Carl’s three adult children – barely-functional neurotic Nathan; washed-up screenwriter Beamer, who spends every Thursday evening reenacting kidnapping scenarios with a dominatrix called Lady; and clever Jenny, whose ambition is to get as far away from the family pile as possible. As they prove, money doesn’t make you happy – or particularly nice.
“You can write anything you want about sex,” she says. And she does – even more so in this new novel. “But you cannot talk about money.” And yet, she says, it is at the heart of everything. “Nobody really knows how much money is enough money, or how much money is too little money. All you really know is that you don’t have as much money as other people, but you don’t have as little money as other people. So how do you even talk about it?” she asks. “There are a lot of very wealthy people who, because of their proximity to much wealthier people, don’t feel wealthy.”
In her profiles, Brodesser-Akner likes to ask people to describe their childhood bedrooms, a tip from an early mentor, the journalist David Hochman. “It’s such a good question because it forces you, instead of leaning forward, into sort of leaning back, being contemplative about your childhood. It gets you the best answers in the world,” she says. But it is one she struggles to answer. “My childhood bedroom was always in a state of wondering what it should be,” she says, eventually.
Her father, a computer consultant who later became a teacher, came from a wealthy part of Long Island; her mother was a secular Israeli, who moved to America in the early 60s, when she was 15. The first time her mother went into a synagogue, so the story goes, was when she got married. She became very religious when Brodesser-Akner was 12, after sending her older two daughters to Jewish Schools; “she loved the Shabbat candles and stuff and decided she wanted that for us”. After her parents’ divorce, when Taffy was six, they shuttled to and fro between their father’s house in Long Island and the much less affluent Canarsie, Brooklyn, where her mother lived. She has a younger sister from her mother’s second marriage. The girls were forever worrying “were we rich or were we poor?”
The bedroom she settles on is the one in Carnarsie, which had a Hebrew Thelma and Louise poster on the wall brought back from a trip to Israel. “And here’s the sad answer to your question,” she says finally, “after I left home for college my house burned down.” She’s right, it’s a good question.
Around the same time that her mother and elder sisters found their faith, Brodesser-Akner discovered Philip Roth. Her mother banned her daughters from reading teen fiction like The Babysitters Club or Sweet Valley High books because the girls on the cover looked “too sweaty and she thought everyone inside them was having sex”. So 12-year-old Taffy picked up the Roth novels that her sister bought home, with their picture-less jackets. “They were the dirtiest books and I loved them,” she laughs. They taught her what to want from a novel, priming her later appetite for plotty, American big hitters like Franzen and Donna Tartt. “They were incredibly emancipated from shame and self-consciousness. That was their maleness to me.” They also taught her how she wanted to write, and it was this sense of liberation that led her, like Libby in Fleishman, to men’s magazines, and a staff-writer job on GQ.
Unlike others in her family, Brodesser-Akner doesn’t consider herself a practising Jew – although her mother hasn’t given up hope. Her husband converted to Judaism before their marriage and they send their sons to Jewish schools. So quite Jewish then? She laughs: “I’m very indoctrinated toward religion. But I resist it.”
Her upbringing has left her wary of any sort of magical thinking. “If you subject yourself to the powers around you then your success and your failure belongs to them,” she says. “It’s very easy to decide that you’re not inspired today or that a muse has left you. My muse has always been my mortgage and bills to be paid. If you treat writing like a job and you refuse to let mystical aspects into it, then you’ll get it done.”
But she is not entirely immune to superstition – or writers block. She was struggling with a section in the latest novel in which younger son Beamer, failing in his marriage and his career, is hurtling towards a breakdown. In one memorable scene his wife drags him to a psychic, and Brodesser-Akner took herself to one on the Upper West Side for research. The psychic determined that her third eye was cloudy. “It sounded so correct to me. I had not considered that my third eye could be blocked, so I said, ‘Here just take my money.’ Then I wrote the Beamer section!” she declares triumphantly. “So what do we say about it? It cost me $100 – and I don’t easily part with $100.” When she called the next day, the psychic told her to come back and bring $500 dollars, at which point Brodesser-Akner hung up. Her work was done.
Her superpower is the ability to spend hours at her desk (she doesn’t do yoga breaks); she compares herself to Sisyphus, relentlessly pushing that boulder up the mountain. “And I wondered, what if this was happy?” she asks. The answer is clearly “yes”. She loves this stuff. Finally relieved of the weight of the Difficult Second Novel, she has already started not one but two third novels, “writing between the rain drops” as usual.
The New York Times will have to fire her before she gives up the profile gig, she says. “It’s the most wonderful job, in a way that even writing novels is not.” She is acutely aware that readers have paid for her novel. “I feel like I have to be dancing on every table and entertaining at all times.” Her rule, for both fiction and journalism, is “to remember who you work for, which is the reader”. And if that means writing a profile that makes a celebrity choke on their green juice, then suck it up! “You do what you have to do,” she says. “But don’t do it with me,” she adds with a big laugh as we prepare to cross the buggy barricades, damp and rigid with cold. “Be nice to me!”
• Long Island Compromise is published by Wildfire. To support the Guardian and Observer, order your copy at guardianbookshop.com. Delivery charges may apply.
