Oprah Winfrey makes ultra-rare appearance with longtime love Stedman Graham amid major milestone

Oprah Winfrey made a rare appearance with her longtime love, Stedman Graham, as she celebrated the 40^th anniversary of her hit series, The Oprah Winfrey Show, in Chicago.

The talk show legend was joined by Stedman at the special event, as they posed with a large platter of fried chicken alongside her former private chef, Art Smith.

Oprah was glowing in a cream co-ord look paired with white sneakers and tinted sunglasses, while her 75-year-old partner stood by her side in a black suit and white button-up shirt.

Oprah and Stedman’s 40-year romance

Oprah and Stedman have been together since 1986, and have kept their relationship out of the public eye in recent years, with the pair not making an appearance as a couple since 2019 at the Tyler Perry Studios opening gala.

The 72-year-old shared that their decision to step back from the limelight as a couple came down to the constant tabloid stories about them. During an interview on the Goop podcast, Oprah revealed that she even sought advice from poet Maya Angelou on how to deal with the noise.

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“Every time I would get so upset about it, Maya would say, ‘Babe, you don’t have anything to do with that,'” the TV personality recalled. “I’d say, ‘But they’re saying, and it’s not true. You don’t know what it’s like when people are saying things about…’ It’s been happening so long.”

“She actually said, ‘Whoever’s sitting at the typewriter, they’re thinking, What can we say this week that’s going to sell some stories?'” Oprah continued. “It’s also why I stopped making as many public appearances with Stedman because I realized that every time there’s a new photograph, there’s a new story.”

Their decision to avoid marriage

The power couple are famously unmarried, and Oprah shared insight into the reason why they called off their engagement in 1993 yet decided to stay together. 

“I realized I didn’t actually want a marriage. I wanted to be asked,” she wrote in a 2020 essay for O.

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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. He and I agree that had we tied the marital knot, we would not still be together.”

Despite this decision, Stedman is devoted to Oprah and has been for 40 years. 

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“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.”

“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 explained. “I’m happy with that.” Stedman is a businessman, author and public speaker, and runs his own marketing firm.