When Oprah Winfrey took the stage at Sunday night’s Golden Globes to accept the prestigious Cecil B. DeMille lifetime achievement award, there was no one in the room who looked prouder than her longtime partner, Stedman Graham.
In the hours leading up to her big night, Graham played his most familiar role, as Winfrey’s biggest fan and support (and she, his). The media mogul, 63, called Graham, 66, her “rock” and even posted a sweet shout-out to her sweetie on social media prior to the awards ceremony.
“Stepping out with my HoneyGraham! thanks @versace_official. Great experience working with team #VERSACE 👏🏽👏🏽to you all,” she captioned the post, which featured two photos of the couple—one showing their full-length outfits and the other in more close-up. Here, take a look back at Winfrey and Graham’s rock-steady relationship over the years.
The pair first met in 1986, when Winfrey was still based in Chicago. Though they got along well when they were first introduced to one another, Winfrey and Graham didn’t fall into a romantic relationship until a few years into their friendship. According to a People magazine cover story in 1992, when they did start dating, they took things slow, with Graham commuting into Chicago on the weekends from a modest apartment in High Point.
Though reporters constantly dogged them about marriage, neither Winfrey nor Graham seemed to be in a rush to the altar. For the first six years of their relationship, the couple laughed off questions about when they were planning to get married, with Graham saying during a rare appearance on The Oprah Winfrey Show in 1989, “We will announce happily when we’re getting married when we decide, and not before.” When tabloids tried to break news of a happy engagement in 1991, Graham dismissed the rumors. “It was news to me,” he said.
The pair got engaged in 1992—but ultimately never married. According to reports, Graham popped the question while Winfrey and her best friend, Gayle King, were hanging out at Winfrey’s Indiana farmhouse, but the proposal was so matter-of-fact that Winfrey had to check that he was actually asking. “Is this the proposal?” she asked, according to the People feature, to which he replied, “I want you to marry me. I think it’s time.” They set a wedding year for 1993.
Winfrey says she has no regrets about ultimately deciding not to go through with the wedding. “Nobody believes it, but it’s true. The only time I brought it up was when I said to Stedman, ‘What would have happened if we had actually gotten married?’” Winfrey told Vogue in an interview published last August. “And the answer is: ‘We wouldn’t be together.’ We would not have stayed together, because marriage requires a different way of being in this world.”
“His interpretation of what it means to be a husband and what it would mean for me to be a wife would have been pretty traditional, and I would not have been able to fit into that,” she added.
She briefly contemplated marriage again in 2013, after attending Tina Turner’s wedding in 2013. But the media mogul told Access Hollywood that she only confirmed her beliefs after a little bit of reflection. “I think that it’s interesting that you would ask [about marriage] because I thought about it at Tina Turner’s wedding, because Tina was like, ‘Oprah, you need to do this. You need to do it.’ I was just thinking, ‘Well, OK, would things really be different?’ And no, I don’t think so.”