E. Jean Carroll has lived several American lives, all worthy of their own headlines.
Before she became the advice columnist who could turn heartbreak, horniness and human folly into copy, Carroll was Miss Cheerleader USA, a beauty queen, a sorority sister and, eventually, one of the rare women to crash the boys’ club of glossy magazine journalism and not merely survive it, but redecorate the place in her own voice.
Esquire, Playboy, Outside, Elle—Carroll flourished during the golden age of glossy magazines with a preternatural combo of charm and wit.
In Ivy Meerapol’s new documentary, Ask E. Jean, that life is a case study in voice—how one gets it, how one performs it, how one loses it under trauma and how, sometimes very late in the game, one takes it back.
Meerapol, whose previous films include Roy Cohn: Bully, Coward, Victim; After the Bite; and Heir to an Execution, did not come to Carroll as a lifelong devotee of the “Ask E. Jean” column. Her entry point was the 2019 New York Magazine excerpt from Carroll’s book, What Do We Need Men For?, in which she publicly accused Donald Trump of sexually assaulting her in a Bergdorf Goodman dressing room in the mid-1990s.
“I read that and thought, ‘This is a very unique voice,’” Meerapol says.
The film follows that voice back to its source: Carroll’s early career, her move to New York City after years of trying to get published and her rise in the male-dominated world of magazines. This was the era of big bylines and bigger egos, of Hunter S. Thompson and Graydon Carter, of literary machismo lacquered in cologne and expense accounts. Carroll found a way through it by being faster, funnier and more fearless than the others in the room.
Then the film shifts into the event that would reorder the meaning of everything that came before it.
According to Carroll, she encountered Trump at Bergdorf Goodman. The exchange began as banter—“Hey, you’re that advice lady,” he says; “Hey, you’re that real estate tycoon,” she replies—and curdled into assault in a dressing room. Meerapol’s film is especially attuned to the strange, misunderstood behavior of trauma: Carroll’s shock, her laughter, her attempt to process the unprocessable as if it were another absurd anecdote from the city.
That, too, is part of the story. Not simply what happened, but what Carroll could not yet say about what happened.
Twenty-five years later, the Me Too movement changed everything—women were speaking their truth; journalism was making room for testimony; and Carroll, who had spent a career advising other women, began reckoning with her own silence. She made a list of what she called her “hideous men.” Trump was on it.
When her account became public, Trump denied it and called her a liar. For Carroll, a journalist whose credibility was the engine of her life and career, the attack was another violation.
The legal saga that followed gives Ask E. Jean its courtroom spine. Carroll sued for defamation; then, under New York’s Adult Survivors Act, she was able to sue for the assault as well. “Spoiler alert: She won. She won both,” Meerapol says. The first jury found Trump liable. After he defamed her again, a second jury awarded Carroll $83 million.
But Ask E. Jean is not merely a courtroom victory lap. Its richest moments are messier. Meerapol includes archival material that complicates Carroll, including an appearance during the Anita Hill era in which she voiced attitudes that many viewers may find jarring today. For Meerapol, that discomfort is the point. Carroll’s story is not about immaculate sainthood. It is about evolution.
“That’s so important,” Meerapol says of showing Carroll’s trajectory. “It became a very important mission for us with the film to show how, at age 75, she’s reckoning with the advice she gave to other women but also that she didn’t take her own advice.”
Ask E. Jean understands that reclaiming one’s story is not a tidy act. It’s inspirational but awkward, painful, expensive, public and, in Carroll’s case, conducted under what she calls “an avalanche of slime.” Yet, the film insists on celebration, too—Carroll did not simply endure. She changed the record.
‘Ask E. Jean’ plays throughout the Bay Area.




