Oprah Winfrey and Stedman Graham have been together since 1986, and he actually proposed to her—but she didn't say yes. She explained why on an episode of Super Soul Sunday (via Entertainment Tonight), saying, "The moment he asked me to marry him, I was like 'Oh, God! Now I actually have to get married?' But what I realized is, I don't want to be married. Because I could not have the life that I created for myself. I couldn't do it."
However, Winfrey's own mother, Barbara, hinted to the Daily Mail that the talk show titan's relationship with BFF Gayle King is to blame, as well as Winfrey's fortune. "Stedman isn't a good steward of money and that suits Oprah fine," Barbara said. "He is financially dependent on her. He knows her secrets and she knows his. Why would they marry now? He's there at her beck and call. He knows his role in her life." She added, "Gayle is very, very present. I don't know any man I've ever dated who could tolerate that, but Stedman knows Gayle's going nowhere. They speak on the phone three or four times a day…[their relationship is] unhealthy…I can only say what I saw and observed over the years. Gayle was more present than Stedman."