Oprah Winfrey and Stedman Graham’s Complete Relationship Timeline

Oprah Winfrey is one of the most recognizable women in the world. But her longtime romance with entrepreneur Stedman Graham has been kept intentionally low-key. After meeting at a charity event in 1986, he’s been the main man in Winfrey’s life for more than 30 years. Although the couple opted not to marry, their commitment to one another speaks volumes. Ahead, a look back at the major moments in their decades-long relationship.

1986

According to Vanity Fair, Stedman and Oprah met at a charity event in Chicago the same year The Oprah Winfrey Show premiered. In a column O Mag‘s February 2020 issue, Winfrey reflected on seeing Graham around town, but “he was always with the same girlfriend.” Then one day, they found themselves both single and at the home of a friend who was ill.

“We left together, and I asked if he wanted to get a beer. (Yes, I drank a lot of beer then and wore cowboy boots every day.),” Winfrey wrote. “He said he didn’t drink. (Still doesn’t—not one sip of nothin’ alcoholic since I’ve known him). I thought he was nice enough, but I wasn’t that impressed. He was polite, yes, and kind. The sort of guy who sits with an ailing friend. Tall and handsome, for sure. But actually too handsome, I thought, to be interested in me.”

Graham had been previously married to a woman named Glenda Graham in 1974 and welcomed a daughter, Wendy. But Winfrey told People magazine that her producers were suspicious of the 6’6″ former athlete and sportswear model. “They figured if he looked like that, he either had to be a jerk or want something,” she told the outlet in 1992. “He’s kind and supportive…Lots of people want to ride with you in the limo. But you want someone who’ll help you catch the bus.”

1987

In one of only three appearances Graham would ever make on Winfrey’s talk show, he surprised the host. While filming a viewer Q&A, Graham called in to ask Winfrey about what she’d been telling best friend Gayle King about their relationship. She recognized her boyfriend’s voice right away, calling him “Steddy” and speaking with him for a few minutes in front of her studio audience.

1988

The following year, Winfrey opened up on the November 15 episode of her show about her weight-loss journey. She clarified that the 67-pound transformation had nothing to do with her relationship. “I love Stedman very much,” Winfrey said. “And he cares about me and has been very supportive of me, fat and thin. I did not do this for Stedman…You know you cannot do it [lose weight] for anybody but yourself.”

Winfrey reflected on that segment of her show—and time in her life—in 2011. She admitted that part of her motivation for wanting to lose weight was feeling that she “didn’t match what he was in his physical stature.” Winfrey continued, “He’s a very good-looking guy. And I knew that when people would see us together that the first thing they were thinking—I certainly thought for myself—what they were thinking was, ‘What’s he doing with that fat girl?'”

1989

Then rumors of infidelity plagued Winfrey and Graham’s three-year relationship. Gossip columnist Ann Gerber originally alleged in The Chicago Sun-Times that Graham had been cheating with Winfrey’s hairdresser. Days later, Gerber retracted the story in the Chicago Reader. “If I made a mistake, it was in trying to help Oprah with her pain about the rumor and in agreeing to run a second story,” Gerber said in a press conference at the time.

During his second of three appearances on The Oprah Winfrey Show, Graham told Winfrey’s live studio audience, “We will announce happily when we’re getting married when we decide, and not before,” per People.

1992

After six years together, Graham and Winfrey announced their engagement in a 1992 People cover story. According to the outlet, Winfrey and King were at home waiting for Graham to bring home a tape of the latest Oprah Winfrey Show episode. But when he arrived, he popped the question. “Is this the proposal?” Winfrey asked. “I want you to marry me. I think it’s time,” he responded. “Ah, that’s really great,” she remembered replying.

There was no ring (“If you’ve all noticed or watched over the years, I don’t wear rings”) and the couple had just moved into together in 1991. Still, the pair set a tentative wedding date for 1993. That date came and went—the couple never ended up tying the knot.

1997

The couple became more tight-lipped about their relationship after that (Winfrey halted work on a 1993 autobiography), although they still made time for a few red carpet appearances. Graham enjoyed a moment in the spotlight when a February 1997 New York Times profile about him was published. Titled “They Used to Call Me Oprah’s Boyfriend,” the business man spoke about what it was like to be with such a high-powered woman. “People didn’t know anything about what I do or what I’m involved in,” Graham said, “sipping hot tea,” the outlet noted. ”They say, ‘Wow, where did this guy come from?’ ” But the sports management firm founder said, “I’m stepping out. I know there is going to be backlash at some point.”

1998

The next year, Winfrey won a Lifetime Achievement Award at the Daytime Emmys. During her emotional acceptance speech, she thanked her partner of more than a decade.”Stedman, you’re the sweetest man, with the greatest integrity,” Winfrey said as the camera showed a tearful Graham.”Thank you for helping me to be everything that I am, and all that is to come.”

2002

In 2002, Graham accompanied Winfrey to the Emmys again. That evening, Graham wore a dark suit and Winfrey a pale yellow Bradley Bayou gown. A clearly moved Graham watched Winfrey win the first-ever Bob Hope Humanitarian Award.

2008

Winfrey spoke about what kept her 22-year relationship with Graham strong to E! News. “I happen to be with a man who has always appreciated the fact that I was…considered a powerful person,” she said. “[He’s] not trying to crowd in on it, not competing with it. He knows how to hold his own.”

2010

Two years later, Graham made his third and final appearance on The Oprah Winfrey Show, more than 20 years after his last outing. In a behind-the-scenes clip of the show, Winfrey’s last “Favorite Things,” she said: “I think people are fascinated with the relationship because you haven’t seen him, people haven’t seen him and they want to know, ‘What is it? Is it real? What is the relationship really like together?’ And when you see us, it’s really quite normal.”

Graham explained, “We want each other to succeed. And I want her to succeed and to 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 money.”

2013

Questions about why the couple never married persisted well into their more than two decades together. “If you ever interviewed him, he would tell you that had we married, we would not be together today,” Oprah said to Access Hollywood. “Because he’s a traditional man, and this is a very untraditional relationship.”

2015

Then the longtime couple became grandparents when Graham’s daughter from a previous marriage had a baby, per The Daily Mail.

2016

When Star magazine reported Winfrey and Graham had secretly walked down the aisle, Winfrey dispelled the rumors herself on Twitter. On September 5, she tweeted, “6 people who know me well have called today congratulating me or surprised they weren’t invited to my wedding. IT’s NOT TRUE!!”

2017

While gracing the September cover of Vogue, Winfrey reiterated that had they married, it wouldn’t have lasted. “Nobody believes it, but it’s true,” she said. “The only time I brought it up was when I said to Stedman, ‘What would have happened if we had actually gotten married?’ 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.”

2018

In January, Winfrey received the Cecil B. DeMille award for lifetime achievement at the Golden Globes. During her speech, she made sure to thank Graham for his longtime support. Winfrey listed off the many people who had “inspired,” “challenged,” and “sustained” her over the years. Among those were “Gayle, who’s been a friend and Stedman, who’s been my rock.”

Graham was asked by the Los Angeles Times after the speech whether Winfrey would run for President in 2020. “It’s up to the people,” he said simply. “She would absolutely do it.”

Winfrey shared snaps from the evening to Instagram, referring to Stedman as her HoneyGraham.

Shortly after, Leslie Jones and Chris Redd parodied Oprah and Stedman’s relationship on an episode of Saturday Night Live. The pair joked about speculation Winfrey would run for office during a segment of “Weekend Update.”

In March, Winfrey opened up to Gwyneth Paltrow on her Goop podcast about why she keeps her relationship private. “It’s also why I stopped making as many public appearances with Stedman because I realized that every time there’s a new photograph, there’s a new story,” Winfrey said, per People.

2019

May brought the release of Graham’s book, Identity Leadership. Winfrey posted about the release, along with a sweet video of her man, on Instagram. “Honey Graham, I know how much this means to you. Congratulations!” she wrote.

Around this time, Graham appeared on Ellen to promote the book. Naturally, he spoke about the secret to their long-lasting love. “The thing about our relationship is I want the best for her,” he said. “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 it.”

He continued, “For me, I’ve been able to find my own happiness, and develop my own skills, my own talents, my own abilities and I’m satisfied with that. So, the combination, when you have a good partner that’s able to self-actualize their potential and you’re able to self-actualize yours, one and one equals about six.”

2020

Winfrey reflected on her relationship of 33 years in her “What I Know For Sure” column for O Mag‘s February issue. She answered once and for all why she said “yes” to Graham’s proposal but then never married him:

“For years, there were hundreds of tabloid stories, weekly, on whether we would marry. 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. 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.”

Once the COVID-19 pandemic hit, Winfrey gave Oprah Magazine‘s digital director Arianna Davis a look insider her quarantine on Instagram Live. She revealed that Graham was staying in the guesthouse, as Winfrey had just had pneumonia months earlier. Still, Winfrey said she had been having “love chats” with Graham outside of his window. “My friends say ‘Oh, isn’t Stedman upset?’ He’s really not. He’s happy to keep me safe,” she said. But in April, after 14 days apart, the couple’s reunion was captured on Instagram. They look just as excited to see one another as they might have in ’86.

2023

While promoting the new release of the musical The Color Purple, Winfrey shared details of her romance in a cover story with People.

“The most romantic thing I do is make hot water cornbread,” she said, sharing the recipe for the pan-fried cornmeal cakes which requires cornmeal, water, and oil.

“Mothers around the world feed their children on it and all you do is add the hot water to the meal and you make these little flat cakes and you fry them in a pan,” she explained. “Every time I do it it’s like the most romantic thing I’ve ever done.”

As for what Graham does to show his love, it’s also very simple.

“The most romantic thing he does for me at this point is going to the corner every Sunday and getting The New York Times and bringing it in to me,” Winfrey shared.

She also talked about Graham’s favorite food being octopus.

“Stedman likes it for breakfast,” she added, claiming a whole octopus can be found in her refrigerator on a “regular basis.”

“The tentacles and the head are there. He likes it seared [or] sautéed with okra and greens,” Winfrey continued. “He’s the only one who eats it,” adding that “you have to go to a special fish market to get it.”