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

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!”

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!”

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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.” 

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“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.)”

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“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.”

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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.”

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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.”

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“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.”