Oprah Winfrey and Stedman Graham are reminding everyone that one of Hollywood’s longest-running romances is still going strong.
The television icon made an ultra-rare public appearance with her longtime partner in Chicago as she marked a major milestone — the 40th anniversary of The Oprah Winfrey Show.
Oprah, 72, and Stedman, 75, were photographed together during the celebration, posing alongside her former private chef, Art Smith, while holding an enormous platter of fried chicken.
Oprah looked relaxed and glowing in a cream-colored matching outfit, white sneakers and tinted sunglasses. Stedman kept things classic in a black suit with a crisp white button-down shirt.
The sighting immediately stood out because the notoriously private couple has largely disappeared from the public eye together in recent years.
Oprah and Stedman began dating in 1986 — the same year The Oprah Winfrey Show launched nationally — and their relationship has now lasted an incredible four decades.
Despite Oprah becoming one of the most famous women in the world, the pair have deliberately kept much of their romance behind closed doors.
Their last major red carpet appearance together came all the way back in October 2019, when they attended the grand opening gala for Tyler Perry Studios in Atlanta.
Oprah has previously revealed that the nonstop tabloid attention surrounding their relationship played a major role in their decision to stop appearing together so often.
During an appearance on Gwyneth Paltrow’s Goop podcast, Oprah recalled turning to her late friend and mentor Maya Angelou for advice whenever false stories about her personal life became overwhelming.
“Every time I would get so upset about it, Maya would say, ‘Babe, you don’t have anything to do with that,’” Oprah recalled.
She said she would become frustrated when stories were published that she knew were untrue.
According to Oprah, Angelou reminded her that tabloids were constantly searching for something new that would sell.
“Whoever’s sitting at the typewriter, they’re thinking, ‘What can we say this week that’s going to sell some stories?’” Oprah recalled Angelou telling her.
That experience ultimately changed the way Oprah handled her relationship publicly.
“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,” she explained.
The couple has also famously chosen a very different path from many celebrity romances.
Although Stedman proposed and the pair became engaged, they never made it down the aisle.
Their planned 1993 wedding was called off, but instead of splitting up, Oprah and Stedman stayed together — a decision Oprah later said may have actually saved their relationship.
In a 2020 essay for O, The Oprah Magazine, Oprah admitted that she eventually realized she wanted the proposal more than she wanted an actual marriage.
“I realized I didn’t actually want a marriage. I wanted to be asked,” she wrote.
Oprah explained that being chosen by Stedman meant something deeply personal to her, but the reality of marriage was another matter.
“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,” she wrote.
At the height of her career, Oprah said her television show was her biggest priority — something both she and Stedman understood.
“My life with the show was my priority, and we both knew it,” she wrote.
Oprah went even further, saying she and Stedman believe their relationship might not have survived if they had gotten married.
“He and I agree that had we tied the marital knot, we would not still be together,” she wrote.
The couple also chose not to have children together.
Despite avoiding the traditional marriage-and-family route, Stedman has repeatedly made it clear that he remains fiercely supportive of Oprah.
During a 2019 appearance on The Ellen DeGeneres Show, he explained that much of their relationship has revolved around encouraging each other to succeed independently.
“The thing about our relationship is, so I’m dedicated to her happiness, so that’s great for her,” Stedman said.
“And I want her to be the best she can possibly be, and she’s done a pretty good job of doing that.”
Stedman added that he has also worked to create a fulfilling life of his own instead of simply existing in Oprah’s massive shadow.
“For me, I’ve been able to find my own happiness, my own skills, my own talents, my own abilities, and I’m satisfied with that,” he explained. “I’m happy with that.”
Stedman has built his own career as a businessman, author and public speaker, and he operates a marketing firm.
After 40 years together, Oprah and Stedman remain one of entertainment’s most unusual success stories — no wedding, very few public appearances and decades of speculation surrounding their romance.
And judging by their rare Chicago appearance, their unconventional formula still appears to be working.
