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Last month, the Supreme Court refused Donald Trump’s request to review a five-million-dollar civil judgment that found him liable for sexually abusing and defaming writer E. Jean Carroll. The decision cleared the way for a federal judge to finally release the money, plus accrued interest, that had been held in escrow since the jury ruled in her favor three years ago. Carroll has said she plans to use the money to start a foundation for women’s rights, adding, with her characteristic irreverence and wit, that she is also “thinking of getting a toaster.” 

That inclination to find humor even in dark moments is on full display in the documentary Ask E. Jean, released in May, which follows Carroll’s legal fight over what Trump did to her in a Bergdorf Goodman dressing room in the mid-nineties and his ongoing efforts to undermine her account of what happened. Drawing on previously unreleased deposition footage, archival material, and interviews, the movie, directed by Ivy Meeropol, explores why Carroll waited so long to come forward and how she was shaped by a culture that encourages women to stay silent. Ask E. Jean also traces Carroll’s extraordinary life and career in media—from her days as Miss Cheerleader USA to becoming the first female editor at Playboy, Esquire, and Outside, a writer for Saturday Night Live, and a beloved longtime advice columnist for Elle. It’s a portrait of a complex and resilient woman who, despite her legal victories, is still reckoning with the costs of taking on one of the most powerful men in the world. (Back in 2020, Carroll came on CJR’s podcast, The Kicker.)

In May, CNN reported that the Justice Department had started an investigation into Carroll—which resulted in a surge of interest in the documentary. “We had just opened in New York City, and then they announced this,” Meeropol told me. “What we’ve learned is that a lot of people across this country have no idea that Trump has been found liable for sexual abuse and defamation by two juries. They don’t even know, because they’re not getting that news.” I sat down with Meeropol to talk about what inspired Carroll to come forward, why it mattered to build a complete picture of Carroll’s life, and how she managed to make the film fun despite its gravity. Our conversation has been edited for length and clarity. 

SB: How did you come to make this film? What made you want to focus on E. Jean Carroll as a subject?

IM: I just reacted to reading the excerpt from her book What Do We Need Men For? in New York magazine. I had this immediate reaction to the writing—really to the way she was telling the story—and also wanted to know more about her. So that was the moment where I asked my manager to find out: Is E. Jean Carroll doing a documentary with anybody? I wanted to meet her. But now I can really see what was drawing me to her and her voice, specifically, was that she has a way of talking about sexual assault that I hadn’t heard before. She was telling the whole story of how it started as this flirtation and how it ended up in the Bergdorf dressing room. It’s the kind of story that people are so quick to dismiss and say, “Well, what was she doing there? She clearly wanted to hook up with him,” or whatever. It was so much more complicated than that and just felt so real—it felt like the kind of story that women, when they are coming forward with their own experiences with sexual assault, would bury or try to adjust or tailor to what they feel is acceptable.

What really struck me in the film, when I was watching her testimony in the depositions, was that she never seemed to be making an effort to tailor the story or make it into a more stereotypical story about rape or violence.

Exactly. She was never intending to sue him, and so there was never any “Oh, I have to adjust myself. I have to adjust this story because I’m going to court and it’s going to be picked apart.” It was just her voice telling her story because she was ready to tell it, because she’d been inspired by the Me Too movement, but equally by the acts of journalism that brought the Me Too movement to the fore. That was a big thing that was really important to her as well. When the lawsuits did begin, and then you’re in court and you’re being deposed or you’re on the stand, things are a little different, but she never wavered. I was struck by how she told the story, and I wanted to know more about her, and I think I was frustrated that people had announced that the Me Too movement was dead.

In your previous film, Heir to an Execution, you tell the story of Julius and Ethel Rosenberg, who were your grandparents. In many ways, that film is about reclaiming a personal story that has been obscured by a public spectacle. I wonder if that was a thread for you in making this film as well?

I think so, but it’s the kind of thing that I didn’t fully understand until I was in the thick of it. When I was first drawn to E. Jean, I was not consciously thinking in any way about my grandparents or what happened to them or what happened to my father or my uncle. But as I saw all the ways E. Jean was being portrayed and vilified and attacked by Trump and his followers, there were moments of, like, Wow, this is a mob mentality to attack someone who’s trying to tell the truth. The idea of using fear and intimidation, the terrorizing of our country by the Trump administration, brought up similar feelings. So I do think there is a connection there, in that I wanted people to see the E. Jean I see. 

One thing you make very clear in the film is how reluctant E. Jean always was to come forward with this story. She swore the women she told at the time to secrecy. What do you think changed for her? 

I think the Me Too movement, the women who were coming forward—it wasn’t just that they were telling their stories, it was this incredible sisterhood that was happening. E. Jean, in her past, didn’t have as much of that. But even more than that, it showed that the combined voices of all those women and the journalism that brought the stories out actually took down Harvey Weinstein. So a bully, a rapist, someone who’d been getting away with horrific crimes against women for years and years and years and being protected—something could actually be done about it. 

Also, she was seventy-five years old when she first wrote about it for New York magazine. She was ready to look at herself and look at the advice she’d given that she’s now not very proud of. To look at what she had done to accommodate men, and also what it meant to be a member of the boys’ club, which is how she became the first female editor at Playboy magazine, Esquire, Outside, all these men’s magazines in a male-dominated magazine world in New York. She was one of the boys. And I think she realized that can be a dangerous pursuit. She needed to get to a certain point in her life, as a mature, older woman, and be open to listening to the women of the Me Too movement. The other thing is, she was so used to listening to her readers—she was an advice columnist for twenty-seven years—and she talks in the film about how she would get all this information from her readers, so when they started writing to her saying that they were following the Me Too movement and were affected by it, and saying, “I was assaulted too, this has happened to me, what do I do?”—E. Jean actually is someone who really does care about her readers, to the point where she started to feel like she was being a hypocrite for not having told her own story. 

There’s this really uncomfortable moment in the film where you show a clip of her describing Anita Hill and Paula Jones as wimps for how they handled their own sexual harassment. Why was it important to include that? 

That was such an important clip to discover, and we knew when we saw it that we had to put it in. And by the way, E. Jean is mortified by it. But she understands completely why it’s in the film. What was important to me about putting that in is that E. Jean is complicated, and even though she was giving some great advice that was ahead of her time—saying to women, “You don’t need to be married at thirty. Why are you worried about that?” or “You should go to college. You don’t have to just be home taking care of your kids and your husband”—she also wasn’t being a good friend to other women. She thought that women should be more powerful than they actually were, and it wasn’t until it happened to her—and then many years later, when she grappled with it—that she could even see that. I wanted to show that E. Jean is a product of her time. 

Often in media narratives, when something terrible happens to someone, it completely flattens them. So much of the film is about building a portrait of E. Jean beyond this one horrible thing that happened to her. Why was that so meaningful to you? 

I refer back to talking about my grandparents, and how they were flattened. People are flattened over and over again when they become public figures. And it really bothered me how E. Jean was so kind of innocent and naive when she first started going on all the news shows, before any of the lawsuits began. She just went on and was telling her story, and she was ripped apart because she’s an eccentric person, she’s an honest person, there was no media training for her to tell this story, and she was so brave to do that. 

She had said to me early on when we met that Donald Trump, what he also had done to her was reduce her life to those three minutes in the dressing room. And I started to feel like, This is why I am making a film about this person. It’s not just about Carroll v. Trump. This is a much bigger story about what women endure. I felt a really strong responsibility to tell her full story because I also think it’s inspiring.

In the beginning of the film, you use a clip of Alina Habba, Trump’s lawyer, asking Carroll, “If you were concerned about being dragged through the mud, why would you choose to sue Donald Trump?” And she says, “Because he called me a liar. He called me a liar, and I couldn’t let it stand.” And that is clearly also a motivation for her in participating in the film. You’ve said she was hard to persuade. So how did you persuade her? 

I was fortunate that she was open to meeting me, which ended up being over Zoom because it was the beginning of the pandemic. I had made a film about Roy Cohn for HBO that came out in 2019, and she really responded to that. I think we are simpatico in some ways. She’ll say things like, “I just knew Ivy would be fun to be around.” And obviously, that matters to E. Jean.

When I’m getting to know someone who might be willing to be a subject, I share things about myself because I think it’s important to not have it be this one-sided thing. I don’t need to be the mysterious director. It’s a relationship. It’s tricky, though, because she’s a journalist. I will say that one of my greatest moments with her was when we were talking in an actual interview and she stopped at one point and said: “Wow, you’re really good at this.” And I was like, “Oh God, that’s the best compliment I’ve had.” Maybe that goes back to how I persuaded her. It was not just me firing questions at her and her feeling on the spot. I think she felt comfortable with me.

One of the most vulnerable moments in the film is when she talks in a deposition about the guilt she still feels about having gone into the dressing room—for being, as she puts it, “not smart”—even though there are examples in the film of her telling other women that they shouldn’t feel guilt about things like this that have happened to them. Were you surprised that she’s still grappling with that? 

I was. That is one of the most heartbreaking and poignant moments in the whole film. I was surprised because I thought: Okay, she’s been through all of this. Intellectually, she knows that she is not to blame, and that there should be no shame on her side. But to me, the reason it’s so hard to watch is because it just shows how deep it goes. 

That’s how we are just trained to be. I have these conversations over and over again with women now, especially women who don’t believe her, who are like, “She shouldn’t have been up there in that dressing room.” It’s that same idea as she shouldn’t have been having fun at that party or dressed in that low-cut top or doing this or doing that. Why is the onus always on the women to not make themselves too available? This is the thing with E. Jean: her resistance to being a victim went so far that she had to completely divest herself from what actually happened. The idea of being a victim is so anathema to her. The clip where she is talking with a rape victim on her talk show, and she’s giving her all the advice that E. Jean didn’t take herself when it happened to her, that’s really—the film is right there. That was from 1994, before her own assault, which now makes perfect sense. It hadn’t happened to her yet, so she was able to say, “Don’t live in shame, you’re not the victim, and always press charges.” And it makes sense now that, like she says in the film, after the attack at Bergdorf’s, she just started to lose interest in being with men. 

You’ve said that finding funding and distribution for this film was quite difficult. And even after you found funding and got an incredibly enthusiastic reaction from festival audiences, distribution was not easy. Why do you think that is? 

This has been a long haul. Early on, it was less intimidation or fear of retribution from Trump or his people than it was Me Too fatigue. What I would be hearing is, people are just not interested. They’re not interested in the story of a woman being assaulted. We’d already heard about twenty-six other Trump accusers. And who is E. Jean? She’s older. She’s not famous. Why do we care about her? 

And so I really had to go make the film to show why we care. No traditional outlets would finance it, and we raised the funds from foundations and individual funders who believed in E. Jean.

But then we’re making the film and he gets reelected and people drop their names off the film, the credits. We do a premiere at Telluride, which is an incredible opportunity. We didn’t know where we were going to end up. We had this great premiere. We got great reviews. We got a lot of coverage. We were invited to numerous festivals. There’s an audience for this, and they’re responding to the film. But we got not a single distribution offer. That, to me, is clearly because they didn’t want to piss off anyone in the White House.

Speaking of the White House, there have been reports that the Justice Department has opened a criminal investigation into E. Jean. How has that affected her and the film?

E. Jean is just working on a new book and trying not to be distracted by what is clearly a vindictive move that has no legal basis. And I can’t imagine it’s going to go anywhere. What it’s done to the film is created more interest. It amplifies the story that E. Jean prevailed in court twice—and that, in turn, amplifies the film. 

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