By Daily Mail (U.S.) | Created at 2026-08-11 02:49:23 | Updated at 2026-08-11 03:43:50
1 hour ago
Oprah Winfrey posed for a rare photo with her longtime partner Stedman Graham in their first joint sighting in over seven years.
The billionaire businesswoman, 72, posed alongside her partner of 40 years, who is the CEO of his own management and marketing consulting firm, at an event at Navy Pier in Chicago.
She surprised guests at an event celebrating the 15th anniversary of her founding Harpo Studios, her Chicago-based multimedia production company, behind her eponymous talk show.
Winfrey and Graham, 75, posed with celebrity chef Art Smith in photos and videos shared on Instagram by her longtime private chef, as the trio held up a platter of fried chicken at the get-together.
Throughout their lasting romance, Winfrey and Graham have opted to keep their relationship out of the limelight.
And the pair's last joint public appearance was over seven years ago at the Tyler Perry Studios grand opening gala in 2019.
Oprah Winfrey, 72, posed alongside her partner of 40 years, 75-year-old Stedman Graham, at her event at Navy Pier in Chicago over the weekend
It was a rare photo of the longtime couple and marked their first major joint sighting in over seven years; pictured in October 2019
For the occasion, Winfrey wore a cream-colored cropped blazer with a pinstriped pattern paired with matching trousers.
Graham wore a classic black suit sans tie as he supported his longtime partner at the event.
The couple, who are not married, have been together since 1986.
They met the same year that Winfrey launched The Oprah Winfrey Show at a charity event.
They later got engaged in 1992 after six years of dating, but called it off the following year and chose to remain a couple without a traditional marriage.
In a 2020 essay for O, The Oprah Magazine, Winfrey revealed that she started having doubts about their relationship when she accepted his proposal.
'I realized I didn't actually want a marriage. I wanted to be asked,' she wrote.
'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. My life with the show was my priority, and we both knew it.'
Winfrey and Graham posed with celebrity chef Art Smith in snapshots shared by her longtime private chef, as the trio held up a platter of fried chicken at the get-together
She surprised guests at an event celebrating the 15th anniversary of Harpo Studios, her Chicago-based production company, behind her eponymous talk show. The event was held at Chicago's Navy Pier
For the occasion, Winfrey wore a cream-colored cropped blazer with a pinstriped pattern paired with matching trousers. She held up an employee reunion T-shirt that was custom-made for the occasion
Winfrey and Graham, who are not married, have been together since 1986. The couple met that same year that Winfrey launched The Oprah Winfrey Show at a charity event; pictured in January 2018
They later got engaged in 1992 after six years of dating, but called it off the following year and chose to remain a couple without a traditional marriage; pictured in February 2015
In the years since their engagement, both Winfrey and Graham have spoken up about their lasting romance, revealing their secret to their relationship success; pictured in September 1989
She added: 'He and I agree that had we tied the marital knot, we would not still be together.'
Winfrey previously spoke about how her high-profile lifestyle can cause aspects of her life to be subjected to public scrutiny.
And early in her career, she started keeping parts of her life intentionally private.
'I realized that every time there's a new photograph, there's a new story,' she said on Gwyneth Paltrow's The Goop Podcast in 2018.
'I picture [the tabloids], they've got the pictures on the wall. "What do we have this week? What expression do we have? What can we create out of that?"'
In 2019, Graham opened up about his longtime relationship with Winfrey and said he believed the lasting nature of their romance is due to their individuality and support of each other.
'Well, the thing about our relationship is, so I'm dedicated to her happiness, so that’s great for her,' he said on The Ellen DeGeneres Show in 2019.
'And I want her to be the best she can possibly be and she's done a pretty good job of doing that,' he continued.
'And so 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 added. 'I'm happy with that.'
