Oprah Winfrey and Stedman Graham Make Rare Appearance Together for a Very Special Milestone
By Alexus Mosley
Photo Credit: Prince Williams/Wireimage
Oprah Winfrey and Stedman Graham just gave us a rare glimpse of their decades-long romance.
The longtime couple stepped out together in Chicago over the weekend to celebrate the 40th anniversary of The Oprah Winfrey Show, marking their first joint public appearance in nearly seven years.
Winfrey, 72, and Graham, 75, joined friends, family and members of the Harpo Studios team for the special celebration at Navy Pier, where they enjoyed food from Chef Art Smith’s restaurant Reunion.
In a video shared on the restaurant’s Instagram account, Winfrey appeared alongside Graham and Smith as the two men proudly held up a massive plate of chicken wings.
“Hey, Art’s fried chicken!” Winfrey excitedly declared. For the occasion, the media mogul kept things casual in a pinstriped matching set, white sneakers and sunglasses, while Graham opted for a black suit paired with a crisp white button-down shirt and dress shoes.
The appearance was particularly noteworthy considering just how rarely Winfrey and Graham attend public events together. Their last major joint appearance was reportedly in 2019, when they attended the grand opening gala for Tyler Perry Studios in Atlanta. But Graham was by Winfrey’s side for a milestone that holds special significance in her legendary career.
The restaurant celebrated the occasion on Instagram, writing that its team was “filled with gratitude” after hosting Winfrey and the Harpo Studios crew for the anniversary festivities.
Art Smith, Oprah Winfrey, and Stedman Graham at Smith’s Reunion restaurant
Photo Credit: IG @jvanlokere
There’s also something especially sweet about Graham joining Winfrey for the show’s 40th anniversary: their relationship began the very same year. The couple first met at a charity event in 1986, the year The Oprah Winfrey Show made its national debut. They’ve now been together for roughly four decades.
Graham eventually proposed in 1993, but the two never made it down the aisle. It’s a decision Winfrey has openly discussed over the years. Writing for Oprah Daily in 2020, Winfrey explained that although she wanted Graham to propose, she ultimately realized that she didn’t actually want marriage. Her career and the enormous demands of her talk show were her priority at the time.
Their unconventional approach certainly appears to have worked for them. During a 2019 appearance on The Ellen DeGeneres Show, Graham explained that his priority has always been Winfrey’s happiness.
And nearly 40 years after they first got together, he was right there beside her as she celebrated the television show that helped turn her into one of the most influential figures in media history.