Directed by Ivy Meeropol and in select theaters May 22, Ask E. Jean chronicles the journalist's storied career and her experience suing Donald Trump for sexual misconduct twice — and winning

When E. Jean Carroll first came to New York, she didn’t realize how much the city would change her life. “I got one taste of New York, and I thought, ‘Wow,'” the journalist says in the first trailer for the new documentary Ask E. Jean. “I was as happy a being as ever existed.” She landed her dream advice column, then entered the television space. But the dream wasn’t always sweet.

Directed by Ivy Meeropol and in select theaters May 22, Ask E. Jean chronicles Carroll’s storied career as well as her experience suing Donald Trump for sexual misconduct twice — and winning. “He called me a liar, and I couldn’t let it stand,” Carroll says when asked why she brought the case against him.

Carroll came forward with her account in 2019, joining more than 20 other women who accused Trump of sexual misconduct. In 2023, a jury found that Trump was liable for sexually abusing Carroll and defaming her. They awarded Carroll $5 million in damages. Later, a second jury awarded Carroll an additional $83.3 million for emotional and reputational damage. The result was far from the initial expectations that kept her from coming forward when the incident first occurred in the mid-Nineties: “They never would have believed me.”

Prior to 2019, Carroll vowed to keep the alleged assault to herself. In 2024, she told Rolling Stone, “I was never, never, never, ever going to speak on this. Ever. And then both my parents died, and that freed me. I didn’t want to hurt them. It would have killed them. They both died in 2016, and then, just as I was never, never, never going to say a word, #MeToo happened.”

The trailer revisits the trial through the lens of the interrogation Carroll faced in court. “If women could see what kind of questions their fellow woman is asked when she brings charges against a powerful man,” she says. Her statement is followed with exactly that — the audio of Robbie Kaplan asking her, “Were you wearing underwear? Did you wear a bra? Are are you taking any medications or drugs? Have you ever had acting classes?”

For a while, Carroll was reluctant to allow any filmmaker to immortalize her story in this manner. Director Ivy Meeropol changed her mind. “I said, ‘No! No! No! Nooooooo!’ to all documentary filmmakers,” Carroll previously said. “Then I met the stupendous Ivy Meeropol. Only Ivy possesses the wit and grit to capture a dingbat who gives people advice for 30 years, never takes any of it herself, laughs at life’s quagmires and ends up the only person to beat the most powerful man on the planet — twice.”

“Getting to know and create a film about E. Jean Carroll has been one of the greatest experiences of my life,” Meeropol said in a statement. “She is surprising and hilarious, incredibly determined and an absolute inspiration. Her story, and her larger-than-life character, should play on big screens in theaters across the country, and I am beyond thrilled that Abramorama shares that conviction. I cannot wait for audiences to meet E. Jean.”

Ask E. Jean will premiere at the IFC Center in New York on May 22 and in Los Angeles on May 29. Select theaters across the country will screen the documentary with distribution through Abramorama.