Ask E. Jean

The thrilling story of E. Jean Carroll’s life, from her early days as Miss Cheerleader USA to her rise as a trailblazing journalist, author, and beloved advice columnist. Carroll broke barriers as the first female editor at Esquire, Playboy, and Outside, helping to redefine women’s roles in media with her sharp wit and fearless voice. In recent years, she reignited public discourse by standing up to power, becoming the only woman to beat Donald Trump twice in court, and sparking a national conversation about truth, accountability, and resilience. A portrait of an indomitable woman who proved it’s never too late to reclaim your voice, rewrite your story, and change the world.

• Release date
• May 22, 2026
• Runtime
• 91 min
• Genres
• Documentary
• Director
• Ivy Meeropol

Cast

E

E. Jean Carroll Self

L

Lisa Birnbach Self

R

Roberta Kaplan Self

C

Carol Martin Self Donald Trump Self (archive footage)