Skip to main contentSkip to footer

Oprah Winfrey’s surprising confession about romance with longtime partner Stedman Graham

The talk show legend and her businessman partner have been together since 1986


Stedman Graham (L) and Oprah Winfrey celebrate The 75th Annual Golden Globe Awards with Moet & Chandon at The Beverly Hilton Hotel on January 7, 2018 in Beverly Hills, California© Getty Images
Ahad Sanwari
Ahad Sanwari - New York
Senior WriterNew York
September 9, 2024
Share this:

Oprah Winfrey and Stedman Graham have been a quiet power couple for nearly four decades. The two have been together since 1986, and were even briefly engaged in 1992, but never walked down the aisle.

The 70-year-old TV icon and the 73-year-old educator and businessman have been each other's biggest supporters over the years, and while they keep their relationship private, they aren't afraid to riff off each other when the time comes.

The confession came on the season five premiere of The Drew Barrymore Show, which saw the host kick off her Drew's News segment with the hosts of CBS Mornings, Nate Burleson, Vladimir Duthiers, and Oprah's best friend Gayle King.

The conversation turned to a new season of Drew and, hilariously, her tendency to get up close and personal with her guests. The talk show host brought up her similar interaction with Oprah when she was a guest on the show.

After Vladimir, Nate, and Gayle all validated the fact that her personal approach was definitely worth it, she turned to Gayle and mentioned her conversation with "me and your bestie Oprah."

"It didn't bother her," Gayle assured Drew, who quipped back: "And she said that, 'I wish Stedman would touch me like that,' and she was so nice about it!"

View post on Instagram
 

Drew continued: "If a guest starts telling me that, I will back off," with Gayle joking: "Drew Barrymore to Human Resources, Drew Barrymore to Human Resources!"

LATEST: Oprah and Gayle King twin in waterside photo from stunning getaway

In a 2020 essay for Oprah Daily, the media mogul revealed how she and Stedman first met and went from friendship to romance. Explaining that she had initially brushed him off because he was often with the same woman, she wrote: "One day, though, we were both visiting a mutual friend who was ill and later died of AIDS." 

Oprah Winfrey and Stedman Graham attend Tyler Perry Studios Grand Opening Gala - Arrivals at Tyler Perry Studios on October 5, 2019 in Atlanta, Georgia© Getty Images
Oprah and Stedman have been together since 1986

"The guy with the girlfriend had come to the friend's home alone, and so had I. We left together, and I asked if he wanted to get a beer. (Yes, I drank a lot of beer then and wore cowboy boots every day.) He said he didn't drink. (Still doesn't — not one sip of nothin’ alcoholic since I've known him.)"

MORE: Age-defying stars who look far younger than 70: Helen Mirren, Oprah Winfrey & more

"I thought he was nice enough, but I wasn't that impressed. He was polite, yes, and kind. The sort of guy who sits with an ailing friend. Tall and handsome, for sure. But actually too handsome, I thought, to be interested in me."

Stedman Graham hugging Oprah Winfrey, as she shows off the two Emmy awards she won for best TV talk show & best host at the Daytime Emmy Awards, 1995© Getty Images
The couple never married, although they were engaged in 1992 for a year

While those around her warned her about Stedman, assuming he was a "player," she moved hesitantly as well. "I proceeded with caution, even with a friendship. It wasn't until months later, when I learned he'd broken up with his girlfriend and had been inquiring about my dating status, that I gave him a serious thought."

MORE: Oprah Winfrey and Gayle King break silence on lesbian lover reports

She also wrote about their engagement, which only lasted a year before they called it off. The couple have never married during their nearly four decades together. "I realized I didn't actually want a marriage. I wanted to be asked."

Oprah Winfrey & Stedman Graham at the ET/GLAMOUR Emmy Party Celebrating a Night of GLAMOUR, 2002© Getty Images
"I realized I didn't actually want a marriage. I wanted to be asked."

"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."

Sign up to HELLO Daily! for the best royal, celebrity and lifestyle coverage

By entering your details, you are agreeing to HELLO! Magazine User Data Protection Policy. You can unsubscribe at any time. For more information, please click here.

More Weddings

See more