By Page Six | Created at 2026-08-11 18:05:55 | Updated at 2026-08-11 20:04:23
3 hours ago
Oprah Winfrey made a rare appearance with her longtime partner, Stedman Graham, at a party for the anniversary of her iconic talk show.
Over the weekend, the businesswoman celebrated the upcoming 40th anniversary of “The Oprah Winfrey Show” with her former co-workers at Navy Pier in Chicago.
In a video shared on Winfrey’s social media, Graham made a brief appearance, posing with Chef Art Smith at the latter’s restaurant, Reunion.
For the outing, Graham, who is the CEO of his own management and marketing consultancy firm, wore a black suit and white shirt. Meanwhile, Winfrey donned a matching cream pinstripe blazer and pants.
“I cannot even believe that as of next month, September 8, it will be 40 years since we first launched ‘The Oprah Winfrey Show.’ Thank you for being the greatest team ever,” Winfrey, 72, told her former co-workers, per her social media video.
She also said in part in her Instagram caption, “To my Harpo [Productions] crew, for being 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!”
Like her co-workers, Graham has been a supportive force for Winfrey since her show debuted in 1986.
The couple — who are not married — first met at a charity event earlier that year before beginning to date a couple of months later.
They went on to get engaged in 1992 but ultimately called off their wedding the following year.
“I realized I didn’t actually want a marriage. I wanted to be asked,” Winfrey reflected on the engagement in a 2020 essay for OprahMag.com.
She also detailed that if they had ever gotten married, they “would not still be together,” a sentiment Graham agrees with.
“Our relationship works because he created an identity beyond being ‘Oprah’s man’ (he teaches Identity Leadership around the world and has written multiple books on the subject),” she wrote.
“And because we share all the values that matter (integrity being number one). And because we relish seeing the other fulfill and manifest their destiny and purpose.”
Since then, Graham, 75, and Winfrey have kept their relationship mainly out of the spotlight.
The last time the two stepped out in public together was almost seven years ago, at the Tyler Perry Studios Grand Opening Gala in October 2019.
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