Stedman Graham and Oprah Winfrey have one of the most successful relationships in Hollywood. The two first started seeing one another in the late ’80s after meeting at a charity event. Although the pair technically became engaged in 1992, they’ve never actually gotten married. Graham and Winfrey decided long ago that their relationship works best as-is — if it ain’t broke, don’t fix it, as they say — and they have managed to keep their love alive without a wedding (or children). In fact, they called off their engagement in 1993 and never looked back.
As for how the couple makes things work, there’s one thing in particular that Graham credits for the success of his relationship with Winfrey. “Well, the thing about our relationship is, so I’m dedicated to her happiness, so that’s great for her and I want her to be the best she can possibly be and she’s done a pretty good job of doing that,” Graham said during a 2019 appearance on “The Ellen DeGeneres Show.” “And so for me, I’ve been able to find my own happiness, my own skills, my own talents, my own abilities and I’m satisfied with that. I’m happy with that,” he added. And while we can only imagine the pressures of dating one of the most successful women in the world, Graham handles it with relative ease — and there’s a reason.
Oprah Winfrey has no regrets over not getting married to Stedman Graham
During the 25 seasons that Oprah Winfrey hosted her eponymous talk show, Stedman Graham was only seen in the studio a handful of times. One of those times, he opened up about dating the “Queen of All Media,” and the success of their relationship. In a video taken behind the scenes during “The Oprah Winfrey Show,” Graham explained why he’s fine staying out of the spotlight. “We want each other to succeed. And I want her to succeed and be as successful as she possibly can, so I encourage that. That’s not always an easy thing to do when you’re a man in a relationship with a very powerful woman. So I’m not threatened by her fame or her success or her money,” he said.
As for Winfrey, she doesn’t have any regrets about how she’s chosen to live her private life. “Both he and I now say, ‘If we had married, we would not be together.’ No question about it — we would not stay married, because of what that would have meant to him, and I would have had my own ideas about it,” Winfrey told People in 2019. Now living in their golden years, Winfrey and Graham enjoy their lives to the fullest — and they are still each other’s biggest fans.
