Oprah Winfrey revealed the unthinkable during her first sit-down interview with Keke Palmer. The OWN CEO rarely sits on the opposite side and lets someone dig into her personal life. But sharing some never-before-heard stories about her toxic past came so naturally for Winfrey. Palmer, who h as viewed the media mogul as a mentor, got Winfrey to talk about her life before Stedman Graham. Oprah Winfrey opens up to Keke Palmer about the bad men she dated in her early 20’s. (Photo by Axelle/Bauer-Griffin/FilmMagic) Winfrey and Stedman have been in a long-term, unmarried relationship since the 1980s. But she had a few bad apples before then. “There was a guy whose bumper I was holding onto at one point. Literally holding onto the bumper of his car,” Winfrey admitted on “Baby, This is Keke Palmer” podcast. “He slammed the door, and I ran after him, holding onto the bumper of his Datsun Z.” She said, “He pulled off, and I fell. My knees hit the gravel, and everyone in the apartment complex was watching.” When Winfrey caught up to the guy, he told her, “The problem with you, baby doll, is you think you’re special.’ I kept saying, ‘No, I don’t. No, I don’t.’ She was 23 or 24 at the time, but that moment pointed to a familiar pattern and life lesson. Oprah opened up to Keke Palmer about why she used to be attracted to toxic men before meeting her longtime partner, Stedman Graham, revealing that the relationships she witnessed growing up made her gravitate toward men who made her feel like she wasn’t good enough She… pic.twitter.com/GrTGWICXTf— Killa (@KillaKreww) July 21, 2026 “Later, I realized I had become the very woman I promised I’d never be. I grew up watching my mother’s cousin stay with a man who abused her,” Winfrey explained. “I always said I’d never live that life. Standing there, clinging to the bumper of that car, I saw myself repeating the same pattern. She said it was difficult watching the women in her family “sacrificing their power for men.” “I saw myself. I saw my history. I saw generations of women in my family who had sacrificed their own power for men. That’s when I said, ‘I’m going to turn that around’.’ From that point on, I started attracting a different kind of person.” “Listen up … cause she speaking all facts. A [man] doing you dirty; you’re letting him, and until you learn, you’ll keep suffering,” said one person. Another wrote, “Wow, very insightful gems being dropped. I’ll say this, it’s a lot easier to fall into abusive/unhealthy patterns that you observed at home despite swearing you’ll never be that person. It’s definitely a journey to break the cycle.” “Sounds like Oprah finally got the cheat code for self‑worth upgrades,” noted a third person. View this post on Instagram A post shared by Oprah (@oprah) Still, not everyone was sympathetic, as some pushed back, claiming, “This is someone else’s story. She’s lying.” Winfrey met Stedman in her early 30s, when she had more money and more sense. It was 1986 and her self-titled talk show. Although they became engaged in 1992, the couple chose not to marry. Winfrey has said that decision helped strengthen their relationship because neither felt pressured by traditional expectations. Over the years, she has credited Graham with supporting her success while giving her the independence she values. Nearly four decades later, they remain one of Hollywood’s longest-lasting couples. “In 1993, the moment after I said yes to his proposal, I had doubts. I realized I didn’t actually want a marriage. I wanted to be asked,” she wrote in Oprah Daily. “I wanted to know he felt I was worthy of being his missus, but I didn’t want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work. My life with the show was my priority, and we both knew it. ‘My Knees Hit the Gravel’: Oprah Winfrey Says She Once Clung to a Car Bumper After Chasing a Man Who Didn’t Think She Was ‘Special’ ...read more read less