Is this the female Philip Roth?

Debut novelist Taffy Brodesser-Akner has written a book about a middle-aged Jewish doctor - and the plaudits are coming in thick and fast


From page one, Toby Fleishman comes across as a Philip Roth-esque character. Diminutive and Jewish, approaching middle age, a doctor in New York who is out-earned by his peers, disparaged by his daughter, unexpectedly desired on dating apps and in the process of divorcing his shrewish wife Rachel, his life is spiralling out of control.

In fact, Toby is the creation of debut novelist Taffy Brodesser-Akner, a New York Times journalist known for her searing, intimate profiles, including one of Gwyneth Paltrow that went viral. Fleishman is in Trouble, covering the summer Toby and Rachel split up, is a momentous achievement; a genuinely funny and accessible literary novel.

She acknowledges Roth as an influence, alongside writers like Jonathan Franzen. “I’m very flattered by those comparisons,” she says. “To some extent it’s there because, in anything you do, your tastes are either an imitation of the things you love, or you love those things because they speak to you.”

Unlike Roth, however, Toby’s story isn’t told entirely through the male gaze; it’s narrated by his old friend Libby (they met on gap year in Israel) who, like the author, is a journalist who has spent much of her career writing for men’s magazines. This framing — along with a plot development involving Rachel — means that Brodesser-Akner ultimately tells a far more feminist story. “I grew up on those books and it was only much later that I began to ask what those stories would have looked at from the female point of view,” she says. In some ways, she says, the book “felt to me just like the questions left unanswered by Roth, and his refusal to occupy certain points of view”.

Her desire to tell Toby’s story from multiple perspectives came out of her day job. “When I write profiles I mostly take the word of someone who is sitting there and I mostly believe what they are trying to tell me, but I always wonder what the other characters affected would say,” she says. The reaction from male readers has been that they can sympathise only with Toby, whereas “women almost uniformly tell me that they understood both sides, which I guess is the way it goes”.

Toby isn’t based on anyone in particular — although the seed of the novel came in turning 40 and watching numerous friends undergo divorces, often in couples where women out-earned their partners — but he is a product of Brodesser-Akner’s Jewish upbringing.

“I wanted him to have a chip on his shoulder, I grew up in the Jewish community and knew a lot of short men. The thing many of them had in common was they felt oppressed, which was always very funny, to think of a man as oppressed,” she explains. “Once I had him as a doctor and as short his personality just came through; this thoughtful and deliberate guy who is secretly angry about a lot of things but is always fighting the fact that he is angry.”

A native New Yorker, the book paints a picture of a world she knows well. “None of this happened, but it’s all true,” she jokes. “People have asked me is it this person we know, and the answer is always no. Nobody is a specific person, everybody just stands for something.” Having made her name in observational journalism, she felt this was necessary. “I didn’t feel I had the right to write a novel if I couldn’t really make it up,” she says. “It was beneath my dignity to put in real people and just vaguely disguise them.”

Having written a novel about a marriage ending, Brodesser-Akner stresses that hers — to journalist Claude Brodesser, who converted to Judaism when they married and with whom she has two children — is “good enough that I can write a book about a divorce”. In fact, she notes, it’s about to outlast her own parents’ union.

Looking back three years after she wrote the first draft, she wonders “what was going on for me that I had to write 274 pages about nostalgia and wistfulness and regret when I am largely happy with the life I have chosen and the life I am lucky enough to have”. But it was watching friends post-divorce that drove her to write Fleishman. “I was fascinated by the way they were dating and by their outlook and by the way I’d seen a marriage in beginning, middle and end,” she says. She was also struck by the raw deal so many women got after divorce, “whereas every male friend I have after divorce just becomes an attractive wild tiger”.

Thinking on it further, she suggests maybe she wrote the novel in a defensive way, trying to reconcile her memories of dancing and crying at weddings with the fact that those marriages had ended.

“When someone’s marriage ends it is traumatic for everyone who was there for the marriage.” She cites a recently divorced friend. “I have a lot of guilt about how I told her to marry him in the first place and I rooted for them and I wonder if I did the right thing.”

As much as the book is about divorce, it’s also about Jewishness; all the main characters are overtly, specifically Jewish. Brodesser-Akner says this is another debt to Roth. “The gift he gave to American Jews was airing our dirty laundry in public. We were so interested in keeping our secrets and our true selves inside our homes and assimilating on the outside,” she says. “The most shocking thing he did was not write about sex but to write about Jews and their own ambivalence about what it meant to be Jewish in America. When he finally put that on the table and he wrote about it the same way Hawthorne wrote about being a pilgrim, we were finally made into real Americans. People resented Roth for that, but I’m grateful he did it.”

She trusts readers “to not need to relate to the story in order to like it”adding that “it’s a very Jewish question” to ask if people will understand.

“I have engaged with the world on its terms my whole life, the world assumes Christianity, the world assumes Christmas, the world assumes a barely-there relationship with religion. It felt very good for the assumption inside my book to be Jewish.”

That said, the characters’ Jewishness is not necessarily a facsimile of her own. Brodesser-Akner was raised strictly Orthodox, and after her husband converted, he wanted to live an observant life. Toby’s “incidental Jewishness” is in fact a religiousness she has always desired for herself. “All I ever wanted was to be like a regular American Jew who went to synagogue on some holidays, but I was in a very religious house for most of my life, and then I married a man who was really into it. It’s a funny phrase to use but it’s always been a cross to bear, so it was a pleasure to write about people who did not have a profound relationship with the religion.”

Today, she keeps a kosher home but eats anything outside; observes Pesach to the max but breaks it four hours early. “I have these little rebellions,” she says.

Brodesser-Akner’s dissection of the Fleishman marriage, along with sub-plots involving Libby and Toby’s daughter Hannah, develop into a suggestion that women still exist in a man’s world. Regretfully, she says this is her current conclusion. When we speak, she has just published a lengthy feature on sexual harassment and discrimination at a prominent US retail business. “I don’t have any proof that things have changed enough for me to be able to say it’s not a man’s world,” she says. “There are certain women who are allowed at the table, I believe I am one of them, and I can be very good at what I do, but I am not a man, and I think men are still most valued because I think men are the ones making the decisions about what is valuable.”

As an interviewer, she suggests the women she speaks to are inevitably renegades, just by virtue of having got to the table — “whereas a man can be interviewed just for a nice piece of art. You get a fuller range of the male experience in the world, because the only women we interview are the women who have lived through a struggle”.

Despite her no-holds barred approach — she wrote of Paltrow that the perception of her is “she’s a privileged, white rich lady who is into some wackadoo stuff” — she remains an in-demand interviewer. “People act like we’re vultures but a profile is the ultimate voluntary thing, you sat with a journalist you hung out with me, we did this together,” she says. She never pulls punches, she says, because if someone hates a piece it’s never for the reasons she’d expect.

It was a dream fulfilled to sit down with Paltrow. “I had been wanting to interview her my entire adult life. She just did not disappoint. She was very smart and thoughtful and she was vulnerable with me in a way that I did not expect after what the press had put her through.”

As a journalist, it’s nerve-wracking becoming the subject. “There’s a part of me that any time someone’s writing a profile of me wants to tell them how I would write a profile of them,” she laughs. But she knows speaking to the press is part of the deal as an author, even though she claims “these were just the piddling thoughts of somebody one summer who had a question about whether marriage is a really viable institution if it keeps failing us, and how women are supposed to survive if the rules keep changing on us”.

Weighty questions, and not ones Roth ever asked.


Fleishman is in Trouble is published by Wildfire


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