Media mogul Oprah Winfrey and her longtime partner Stedman Graham reunited publicly at Chicago's Navy Pier on August 9 for an Oprah Winfrey Show celebration.
The event marked the first joint public appearance in nearly seven years for Winfrey, 72, and Graham, 75, who have been together for 40 years. Former personal chef Art Smith joined the couple at the milestone gathering, where he served his famous fried chicken.
Winfrey hosted The Oprah Winfrey Show for 25 seasons from 1986 to 2011, building a syndicated television empire from Chicago. Navy Pier, a historic landmark on Lake Michigan, hosted the private anniversary gathering for former show personnel.
Public Absence From Major Milestones
The rare outing follows years in which Graham was absent from major public events in Winfrey's life. He did not appear alongside her during her televised interview with Prince Harry and Meghan Markle, the premiere of the movie musical The Color Purple, or her public weight loss campaign using GLP-1 medication.
A source who has visited Winfrey's Montecito estate in California told the Daily Mail that Graham's absence is equally noticeable in private. "Not only have I never seen Stedman, but Oprah never even mentions him: it's like he doesn't exist," the source said. Neighbors in Montecito who previously observed the couple walking together also noted that nobody has spotted them together for years.
Montecito is an affluent coastal enclave in Santa Barbara County where Winfrey owns a prominent estate. A separate source close to Winfrey's camp explained that Graham chose to attend the Chicago gathering because of its significance to her career. "The anniversary of her show, that milestone, was way too much of a thing that he couldn't miss," the insider said.
"Stedman doesn't have to be at the Oscars, or a random party or places where Oprah is, because Oprah needs her time to be Oprah at those events," the insider added. "But when it comes to this celebration of her, Stedman wanted to be there as it represented a celebration of how Oprah became who she is." The first source expressed skepticism, noting it seemed unusual for a couple together for around 40 years.
Origins Of The 1986 Chicago Romance
The couple first met in Chicago in 1986, the same year Winfrey's talk show expanded nationwide. Writing in O, The Oprah Magazine, Winfrey recalled seeing Graham with a girlfriend and initially assuming he would not be interested in her.
Their relationship developed after they visited a sick mutual friend together and Winfrey suggested getting a beer. "I thought he was nice enough, but I wasn't that impressed," Winfrey wrote. "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."
Winfrey noted that she and her producers initially wondered if he was a player before discovering he was single. A longtime insider told the Daily Mail that their romance was far more visible in the 1990s. "Believe me, in the 90s Oprah and Stedman were hot and heavy," the insider said, adding that they took romantic vacations without Winfrey's best friend Gayle King and spent time in her Chicago penthouse.
Decision Against Marriage And Children
Graham proposed to Winfrey in 1992, but after saying yes in 1993, Winfrey began having doubts about entering a formal marriage. "In 1993, the moment after I said yes to his proposal, I had doubts," Winfrey wrote in 2020. "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."
Winfrey later stated, "Both he and I now say, 'If we had married, we would not be together.'" Instead, the couple chose a spiritual partnership. When false reports surfaced in 2016 claiming they had married, Winfrey wrote on X, "Six people who know me well have called today congratulating me or surprised they weren't invited to my wedding. It's not true!!" A source told the Daily Mail, "They will never get married. If it isn't broke, why fix it?"
Winfrey also decided against having children after once purchasing an additional Chicago apartment with family plans in mind. She told People in 2019, "I was thinking, 'Well, if we get married, I'm going to need room for children.'" She realized the sacrifices required for motherhood and redirected her maternal energy into the Oprah Winfrey Leadership Academy for Girls in South Africa, which she founded in 2007.
"I have not had one regret about that," Winfrey said. "Those girls fill that maternal fold that I perhaps would have had. In fact, they overfill: I'm overflowed with maternal. They are my greatest, deepest joy. They're the daughters I did not have." The academy will transition to local authority management next year, while Winfrey expands her independent scholarship program for girls.
Role Of Gayle King On Family Vacations
Gayle King, a television journalist and co-host of CBS Mornings, has maintained a close relationship with Winfrey for decades. King frequently joins Winfrey on vacations, including trips with Graham following King's divorce. In a 2021 interview, Winfrey reminded King, "Since after your divorce, you were on every vacation with me and Stedman." King responded, "The three of us have had a wonderful time. If I was the third wheel, I didn't know it!" Winfrey answered, "If Stedman didn't like you, Stedman wouldn't have lasted. Husbands and boyfriends come and go. Best friends last forever."
Persistent speculation regarding a romantic relationship between Winfrey and King has been repeatedly denied by both women. King stated on the podcast Call Her Daddy in May, "If we were gay, we would tell you because, believe me, there's nothing wrong with it. It's just, I prefer a man." Winfrey previously explained, "There isn't a definition in our culture for this kind of bond between women. So I get why people have to label it: how can you be this close without it being sexual?"
King joined Winfrey in Venice last June for the wedding festivities of Lauren Sanchez and Jeff Bezos, alongside guests including Leonardo DiCaprio, Sydney Sweeney, and Tom Brady. King and Winfrey also took yacht trips to Mallorca with Kris Jenner in 2025 and returned to the Spanish island in July this year, while also attending the Tony Awards together. Graham was not present on those trips, prompting one source to remark that he seemed absent from her routine life.
However, a second insider dismissed romantic rumors about Winfrey and King as "ludicrous and asinine," adding, "It has absolutely no basis of realistic truth to it at all." The insider explained, "While Winfrey has never been married, Graham is her soulmate, and King is essentially her work wife. Winfrey's true love has always been her work, with Graham and King coming in as two of the closest people in her life."
Weight Loss Journey And Private Life
During Winfrey's recent weight loss journey, in which she lost almost 50 pounds using GLP-1 medication to quiet food noise, Graham made no public statements. A source remarked, "Even when Oprah managed the big feat of losing almost 50 pounds, Stedman didn't publicly congratulate her." While promoting her book Enough: Your Health, Your Weight and What It's Like to Be Free with Dr. Ania M. Jastreboff, Winfrey told People, "He has absolutely been nothing but supportive through all of it. When he met me, I was 200 pounds. And it's never made one iota of a difference."
Winfrey explained on Gwyneth Paltrow's Goop podcast in 2020 that she intentionally reduced public appearances with Graham to avoid media speculation. "I realized that every time there's a new photograph, there's a new story," Winfrey said. In a 2011 behind-the-scenes video from her talk show, Winfrey noted, "I think people are fascinated with the relationship because people haven't seen him."
A resident near Santa Barbara reported that Winfrey enjoys a secluded lifestyle out of the celebrity spotlight. Graham, an author and business speaker, expressed his support for her career in the 2011 video, stating, "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."
Graham reiterated his sentiment on The Ellen DeGeneres Show, stating, "I want the best for her. So, you know, I'm dedicated to her happiness. And so for me, I've been able to find my own happiness, my own skills, my own talents, my own abilities. I'm satisfied with that." An insider close to Winfrey's camp concluded that Graham was always willing to give Winfrey whatever space she needed, describing their 40-year connection as a true friendship and enduring companionship.
