Among the many gems in Stuart Nadler’s dazzling new novel, The Inseparables, is this: “Nobody wore half a dozen amulets quite like my mother. It’s like she’s the female Mr. T.”

Oona, an orthopedic trauma surgeon in Boston, is speaking to her 15-year-old daughter, Lydia, as they marvel at the vintage author photo on a recently reissued book first published in 1976. That book, also called The Inseparables, is an earnest paean to female pleasure (replete with primal anatomical diagrams and a hot air balloon sex scene) written by a young, bedizened professor of women’s studies. That author is Oona’s mother, Henrietta Olyphant, now 70—for whom The Inseparables remains a source of shame.

“Lydia started to open a copy, and then her grandmother knocked it out of her hands with a wooden spoon,” Nadler writes. “It was a well-known fact that she refused to touch the book with her bare hands.”

Nadler knows how it feels to receive that big box of finished copies: he is the author of another novel, Wise Men, and the short story collection The Book of Life. He is an Iowa Writers’ Workshop graduate and recipient of the National Book Foundation’s 5 under 35 award. He lives in New England and has taught at Bennington College, Boston College, and Connecticut College.

The Inseparables is his third—and funniest—book.

“Humor, for me, is the most beautiful kind of intelligence,” says Nadler, who grew up in a large Jewish family in Boston. “There’s a certain kind of wonderful hostility to [Boston] that doesn’t exist everywhere else....You have to have a sense of humor to sort of navigate that, and that was something that was really important for me to put in this book. It’s there a little bit in the other two books but only sparingly. [The Inseparables], in a way, is the book that’s closest to my real personality.”

Set over several eventful days, The Inseparables assesses three generations of Olyphant women in the aftermath of a tragedy, a trial separation, and a travesty: Henrietta has only chosen to reissue her novel The Inseparables to pay off unexpected debts in the wake of her beloved husband Harold’s accidental death. Oona has temporarily moved back into her mother’s house, in rural Aveline, Massachusetts, while she contemplates divorce from her stoner ex-lawyer husband, Spenser. And Lydia is suspended from her tony prep school when a topless selfie goes viral.

“Shame is definitely the cohesive idea,” Nadler says. “Something is at work in the culture now in a way it never has been—shame is a social weapon, [the effect of] which is something people have to endure so privately. For Oona, there’s this kind of smaller shame of expecting the idea of marriage to make her happy; for Henrietta, her book; and then there’s the sort of microcosm of shame for Lydia in her school and the idea that you can’t ever know what people know about you. That’s something that these characters all have in common.”

Another thing the Olyphant women have in common, historically, is a shrewd demeanor.

“They were the sort of family that kept their declarations of affection silent, or at least repressed them and disguised them as the typical ingredients of mother-daughter-granddaughter dysfunction: guilt, conflict, shame, cookies,” he writes. “All of these, you were to understand if you were an Olyphant, were an acceptable stand-in for love.”

Natural sharers, they’re not: Henrietta holds back on the reasoning behind the reissue; Oona hides a potential suitor in the attic. When Lydia is suspended, they tell Henrietta she’s on “vacation” from school.

“Lydia could already see that her grandmother believed none of this,” he writes. “A vacation? In the middle of the week? Lydia wished that at some point in her future she would inherit a bit of her grandmother’s shrewdness, or at least her pitch-perfect aversion to bullshit.”

At the crux of The Inseparables is the question of inheritance: how much of who we become is based on the nature and nurture of the family we’re from? For Nadler, it remains an ongoing inquiry.

“I feel like one of the great stories in literature is, how does your life turn out?” Nadler says. “Capturing three generations in a family, in one moment, is that story in miniature. No matter how much nature and how much nurture your family gives you, there are always those questions of, am I just going to end up like you people? To what extent does your family determine your destiny? These are the questions I’ve always asked myself, and I think it’s sort of the larger preoccupation of everything I’ve written.”

Megan Labrise writes “Field Notes” and features for Kirkus Reviews.