In Alicia Keys’ 2001 hit “Unbreakable”, she mentioned having a strong relationship where a couple could “be rich like Oprah and Stedman.” For many relationships in the entertainment industry, they don’t last. But it’s 2021, approximately 35-years since Oprah and Stedman’s relationship began, and outside of wealth, the pair is still rich in love. But throughout all of the years, the couple never married. Let’s take a look into Oprah and Stedman’s “nontraditional” relationship.
After a string of relationships with a few people that include major film critic Roger Ebert and composer John Tesh, love would enter Oprah Winfrey’s life unexpectedly in the form of Stedman Graham. An already established businessman, educator, and former athlete, the story of their love began when they first met in 1986 at a charity event. At the time, however, Graham already had a girlfriend.
Oprah recalls the start of their relationship via her O! Magazine, stating that things began to heat up more when the two had a chance run-in while visiting a mutual friend who was ill. The media mogul claims that she was initially unimpressed with Stedman, but remembers how “kind, tall, and handsome” he was. “But actually too handsome, I thought,” she said. “To be interested in me.”
An avid lover of beer, Oprah asked Stedman to accompany her for a drink. She then dispels that some months later, he had been inquiring about Oprah as he was a newly single man. But some folks close to Oprah, including producers of her show, felt that Stedman may have different intentions that did not lead with love. According to Oprah’s recollection, people felt as though Stedman was only after her due to her newfound fame. Those thoughts also entered her mind as well. “I figured he must be a player. So did all my producers,” Oprah wrote. “They warned me not to get involved with that Stedman guy.”
Eventually, after proceeding with caution even throughout the friendship phase, Oprah and Stedman began to fall for one another. Oprah would also launch the first season of her daytime talk show that same year. It would go on to become the highest-rated daytime talk show in American history and last for 25 seasons. Stedman also launched the successful nonprofit organization, “Athletes Against Drugs”.
After years of dating, Stedman decided to take things a step further by asking Oprah to marry him. According to a 1992 interview with PEOPLE, the proposal happened at Oprah’s house where she was hanging with her long-time best friend, Gayle King. How he proposed was so “matter-of-fact” that she initially did not recognize it as an actual one.“I want you to marry me. I think it’s time,” Stedman said to Oprah. She accepted by responding, “Ah! That’s really great.” The PEOPLE cover story lists the couple initially setting a “wedding year” for 1993, but no date.
Over time, the questions would continue to plague Oprah as to when she would be walking down the aisle with Stedman. Oprah would offer faint responses to the media’s questioning, once stating on her show that they will announce it when the time is right and not a moment before.
It’s been many years and the couple has yet to meet at the altar, but their relationship is still solid as a rock. As for Oprah’s reasoning, she finally broke down and confirmed that she leave this Earth as a woman that has not, and will never, be married.
“Yeah, I think that’s my final answer,” she told Access Hollywood reporter Shaun Robinson in 2013. Oprah also revealed that she entertained the thought once again while they attended Tina Turner’s wedding to Erwin Bach in 2013, but felt that things for her, internally, would remain the same.
As for how Stedman feels, Oprah shared that he has accepted being a “traditional man in an untraditional relationship.” She also admits that Stedman feels their relationship would not have survived had they married because she would not necessarily be the “traditional wife.”
Once again, Oprah reflected on their relationship in a January 2020 article for Oprah Magazine. In the write-up, she reflected on the proposal and confessed that she only wanted to be “asked” and to “know he felt I was worthy of being his missus,” but with the show being her life’s work and main priority, she could not risk the commitment. “I didn’t want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work,” she said. Instead, they refer to their longtime relationship as more of a “spiritual partnership.”
Oprah also shares that their decision to marry or to not have children together is one they do not regret. “I also believe that part of the reason why I don’t have regrets is [that] I got to fulfill it in the way that was best for me,” said Oprah, according to People.
