Oprah Winfrey makes rare appearance with longtime partner Stedman Graham at talk show anniversary party

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…

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.

Oprah Winfrey and Stedman Graham smiling at a man holding a platter of fried chicken.
Oprah Winfrey made a rare appearance with her longtime partner, Stedman Graham, during a celebration for the 40th anniversary of her iconic talk show. oprah/Instagram
Chef Art Smith, Oprah, and Stedman Graham holding a platter of fried chicken.
Graham joined the businesswoman as she gathered with her former “Oprah Winfrey Show” co-workers in Chicago. jvanlokeren/Instagram

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!”

Oprah Winfrey in a black dress with Stedman Graham in a black suit, posing arm-in-arm on a red carpet in front of a black backdrop with the Tyler Perry Studios logo.
Winfrey has been with Graham (pictured in October 2019) since 1986, the same year as her talk show’s debut. Getty Images
Stedman Graham and Oprah Winfrey attend the Tyler Perry Studios grand opening gala.
The couple’s last public appearance together was at Tyler Perry Studios Grand Opening Gala in October 2019, as seen above. Getty Images for Tyler Perry Studios

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.

Oprah Winfrey in a pale pink gown, making a peace sign, and Stedman Graham in a black tuxedo stand together.
The duo (seen above in 2015) first met at a charity event in 1986. Getty Images
Oprah Winfrey and Stedman Graham attend the "Selma" and the Legends Who Paved the Way Gala.
Winfrey and Graham (pictured in 2014) got engaged in 1992, but called it off the following year. Getty Images

“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.

Oprah Winfrey and Stedman Graham posing together at the People's Choice Awards.
In a 2020 essay, while reflecting on the engagement, Winfrey (pictured with Graham in 1998) admitted she “didn’t actually want marriage.” Getty Images
Oprah Winfrey in a gold gown and shawl with Stedman Graham in a tuxedo at the Kennedy Center Honors.
“Our relationship works because he created an identity beyond being ‘Oprah’s man,’” Winfrey explained. Getty Images

“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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