Oprah Winfrey Makes Rare Outing with Her Partner of 40 Years — and Netizens Can’t Agree on What They See in the Photos

The acclaimed TV host and media mogul reunited with her former Harpo team in Chicago — and her longtime partner was by her side for the rare public appearance.

The gathering marked the approaching 40th anniversary of “The Oprah Winfrey Show,” but new images of Winfrey and businessman Stedman Graham soon prompted a separate conversation online.

On August 10, 2026, Winfrey shared footage from the reunion on Instagram, explaining that former Harpo parking manager Ty Owens had brought past employees together in Chicago. “I can’t believe that this September 8 marks 40 years since The Oprah Show debuted!” she wrote.

Winfrey thanked Owens for organizing the gathering and former personal chef Art Smith for hosting it at his Chicago restaurant, Reunion. She also praised her former Harpo colleagues, calling them “the greatest team ever.”

“And to ‘all my children’ who got raised from The Oprah Show by me, your mamas, and grandmamas, we’ll celebrate on the @oprahpodcast in September!” Winfrey added.

Winfrey’s friend Jill Van Lokeren shared additional images from the event on the same platform. She described the reunion as “a night of all love and pure joy” and thanked Winfrey, Smith and Owens.

The Reunion Put Winfrey and Graham Side by Side Again

The images show Winfrey standing between Graham and Smith as the group gathered around a large platter of fried chicken.

Winfrey wore a light pinstriped suit with a pale blouse, white sneakers and tinted sunglasses. Her hair fell in loose waves around her shoulders. Graham stood beside her in a dark suit with an open-collar white shirt. He wore his gray hair short and kept his familiar mustache.

In one image, Smith holds one side of the platter while Graham supports the other. Winfrey stands between them. Another frame captures her reacting animatedly as the group poses with the food.

The New Photos Sparked Conflicting Reactions

Once the latest images circulated, netizens began offering very different interpretations of what they saw. On Facebook, one netizen said, “He doesn’t look like he wants to be there.”

In a separate discussion, another commenter focused on Winfrey, writing, “Wow, Oprah shrunk and where did that hair go?” Someone else compared the couple’s appearance, saying, “They have the same hairline.” Another person zeroed in on Winfrey’s hairstyle: “Who did her hair? Oprah needs her bangs back….”

Other reactions centered more heavily on Graham. One viewer wrote, “He looks way older than her.” Another simply remarked, “So weird!” A different person appeared surprised that the man beside Winfrey was Graham, asking, “Is that him!😳”

One person joked, “Bro looked like he just woke up after 7 years. lol. I love both of them.” Another viewer added, “Stedman looks like he can barely see right now…. 🤦🏾‍♂️”

The reunion photos appear to be the latest public images of Winfrey and Graham together. Before this outing, the couple had last been photographed together publicly at the Tyler Perry Studios Grand Opening Gala in Atlanta on October 5, 2019.

At the gala, Graham stood just behind Winfrey on the red carpet as she posed in a long dark gown and he wore a black suit and tie. In another photo from the event, Winfrey spoke with reporters while Graham remained nearby, with Tyler Perry standing beside her.

The public appearance also brings renewed focus to the decades-long relationship Oprah Winfrey and Graham have maintained largely outside the spotlight. Although they once planned to marry, the couple ultimately chose not to tie the knot and have remained together in an unconventional relationship.

How Oprah and Stedman Met

Despite being famous and influential, Winfrey chooses to keep her love life private. For over 30 years, Graham has been a critical support system for the show host. Their commitment and loyalty speak volumes. But, how did it all begin?

A young-looking Winfrey met Graham at a Chicago charity event in 1986. The TV host once said she noticed the entrepreneur moving around town with his girlfriend, but they found themselves single at a friend’s house one day.

The duo decided to step out and have a chat. Winfrey once reflected on their first interaction, noting she was not overly impressed at first, although she found him handsome, too handsome to be interested in her.

Recalling the moment, Winfrey said, “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.) He said he didn’t drink. (Still doesn’t—not one sip of nothin’ alcoholic since I’ve known him).”

The media mogul continued, “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.”

Before meeting Winfrey, Graham was married to Glenda, with whom he had a daughter, Wendy, in 1974. However, the “Oprah Winfrey Network” producer said to People magazine that her producers were wary of the former athlete and sportswear model. They thought he was a fraud.

It Took 6 Years Before Stedman Started Keeping ‘A Toothbrush at [Her] Apartment’

At first, Winfrey said she did not jump into a relationship with Graham. Her friends advised her to keep things simple with him until she was sure he was single and genuine.

The duo only began dating after Winfrey was sure she had made the right choice. However, gaining the trust of one of the most influential black women in the world isn’t an ordinary feat. It took months for Graham to prove his loyalty and support.

Winfrey later remarked that Graham was not one of those who wanted to ride in a limo, but instead, he was willing to “run and catch the bus” with her.

During the early months of their relationship, Graham traveled on weekends from his humble High Point apartment to her luxurious condo on Chicago’s Gold Coast.

Winfrey was headlining her show, “The Oprah Winfrey Show,” at the time. Graham began spending more time in Chicago, working with the non-profit Athletes Against Drugs, which he founded.

Things progressed sweetly between the lovers, but they made sure to safeguard their relationship from the prying eyes of the media. However, Graham sometimes made unannounced appearances on her show.

Graham made a surprise appearance on Winfrey’s show during a viewer Q&A. He dialed in to see whether Winfrey would spill the beans on what she told her close buddy Gayle King about their relationship.

Winfrey and Graham’s romance has been a sweet journey, but one with its fair share of controversies. First, the couple had to deal with media storms, including a false allegation that Graham was having an affair with Winfrey’s hairdresser, which a Chicago columnist spread.

The columnist, Ann Gerber, swiftly issued a retraction and apologized to Winfrey. The lovebirds have had several milestone moments in their relationship. One such moment came in 1991 when Winfrey finally allowed Graham to keep a toothbrush in her house after six years of dating.

Their 1992 proposal was another big moment in their lives. For years, Winfrey had been quizzed on her marriage plans. However, she gave no affirmative response until their engagement in 1992.

The former athlete proposed to Winfrey in style. Winfrey was waiting for Graham to arrive from Chicago and was hanging out in her kitchen with Gayle King. She stepped outside to meet Graham and was stunned when he proposed to her.

Their conversation seemed too casual for a proposal. The pair kept their engagement a secret for a few weeks until Winfrey revealed it during a November guest appearance on King’s TV show.

Why Oprah Will Never Marry Stedman

In her 2020 piece about her romance with Graham, Winfrey recalled the instant joy of being proposed to and then realized she loved her relationship with him as it was.

The media mogul realized she had doubts about being married. In addition, the 68-year-old said she did not want to make the sacrifices of being married. For Winfrey, her show was her priority.

Despite pressure from her famous friends like Tina Turner, Winfrey believes marriage is not for her. However, after attending Turner’s wedding in Germany, the show host considered marrying Graham but had a change of heart.

Winfrey admits that she and Graham would not have lasted if they had married. But, according to the media star, her relationship with the former model is so odd that it wouldn’t have fit inside the boundaries of marriage.

Winfrey said of her decision to stay unmarried, “If you ever interviewed him, he would tell you that had we married, we would not be together today. Because he’s a traditional man, and this is a very untraditional relationship.” The show host believes she does not fit in with the demands of a “wife.”

Their Unconventional Relationship

Although they never got married, Winfrey and Graham enjoy a supportive relationship. According to the longtime presenter, her boyfriend respects her fame and never tries to compete.

Speaking of their relationship, Winfrey said, “I happen to be with a man who has always appreciated the fact that I was…considered a powerful person. [He’s] not trying to crowd in on it, not competing with it. He knows how to hold his own.”

Although she struggled with her physical appearance, Winfrey said Graham was supportive and helped build her confidence. The TV legend remarkably shed some weight but claimed it was not done for her boyfriend.

Winfrey said she did it for herself, even though she loves Graham. She said, “I love Stedman very much. And he cares about me and has been very supportive of me, fat and thin.”

Winfrey believes weight loss should be self-motivated. But, she added, “I did not do this for Stedman…You know you cannot do it [lose weight] for anybody but yourself.”

The couple is now grandparents to Wendy’s child, and the experience has been a lovely one for Winfrey. The media mogul loves her world just the way it is.