Toward the end of Anna Ziegler’s charming, penetrating new play, “The Wanderers,” a successful writer describes watching a famous actress pose a question to one of his heroes, Philip Roth, during a literary gala: “She raises her hand and asks how he would characterize himself — is he Jewish first, or a man, or an American. Or an a–hole … or an artist.”

And what is Roth’s reply? “He said, ‘There is nothing I could say that would not be a fiction except that I am first and last the product of my parents.”

The account is fictional, but the response — at once profound and a copout — should seem entirely credible both to Roth’s admirers and his critics. Ms. Ziegler’s writer, one Abe Hausman, is also the product of his parents and, like Roth, of a diaspora with a complex legacy, in which suffering and accomplishment are inextricably intertwined.

Musing at one point about how to summarize his work, Abe comes up with this synopsis: “He writes books that touch on the American experience but were met with a shrug by both parents, described as too Jewish by his mother and not Jewish enough by his father.” In “Wanderers,” we not only meet that pair, Esther and Schmuli, but see their lives — those of a chasidic couple living in Brooklyn’s Williamsburg neighborhood before its gentrification in the 1990s — juxtaposed with those of Abe and his wife, Sophie, also a writer, who reside in the same area decades later.

There’s also a glamorous movie star in the mix, Julia Cheever — played by the glamorous movie star Katie Holmes — who enters Abe’s life when she appears to strike up an e-mail correspondence with him, after attending one of his readings. Julia happens to be shooting a film adaptation of a Roth novel, and seems titillated by the prospect of bonding with another acclaimed author; Abe, whom Ms. Ziegler identifies in her character listings as an “intellectual who knows he’s an intellectual” and “enjoys seducing with language,” jumps at the bait.

The ensuing virtual relationship exacerbates tensions between Abe and Sophie, who has essentially put her own career on the back burner to focus on her husband and their two young children. In alternating scenes that chart Esther’s own growing aspirations for agency — and reveal that Sophie’s mother endured similar struggles — the playwright cannily demonstrates how conservative and particularly patriarchal ideals, be they rooted in religion or not, can linger in those who fancy themselves most progressive.

If anything, Schmuli, played here with tenderness and gentle humor by Dave Klasko, struck me initially as a more sympathetic figure than Abe, whose exchanges with his wife are pocked with patronizing compliments and unwitting boasts. (“She wanted me to see her,” he tells Sophie, referring to Julia at the reading.) Yet as she has done in previous plays, Ms. Ziegler acknowledges the complicated dynamics between men and women with compassion for both; Abe is not lacking in self-awareness, and in Eddie Kaye Thomas’s carefully textured performance, his inner mensch gradually pokes through. 

Lucy Freyer and Sarah Cooper respectively evince Esther’s and Sophie’s affection for and frustration with their husbands, and show us how that frustration allows these intelligent, passionate women to blossom — though not without cost. Julia is by necessity more of a cipher, an extension of Abe’s sexual and creative longing, but Ms. Holmes’s elegant, measured portrait makes her compelling as such. 

Under Barry Edelstein’s adroit, sensitive direction, “Wanderers” sparkles not only as a study of these engaging characters, but as one of a heritage, and its different cultural variations and generational shifts. As a thoroughly secular Jew, I was deeply moved watching Esther and Schmuli grapple — through different perspectives, and with different outcomes — with the requirements of tradition, and then observing as Sophie and Abe try to thrive on their own terms, albeit with their parents’ examples and burdens never far from their hearts.

In two scenes toward the end of “The Wanderers,” Schmuli and Abe both use the term bashert in reference to their wives. As is the case with many Yiddish words, there is no completely adequate English translation, but father and son use the same words to explain the gist: “the only one for me.”  

You don’t have to be Jewish to get a little verklempt at this point — or to appreciate the eloquence, insight, and deeply humane vision that Ms. Ziegler applies to her wanderers on their disparate journeys.