For nearly 40 years, Oprah and Stedman Graham have been one of Hollywood’s favorite couples. But throughout the media mogul and the entrepreneur’s decades-long relationship, they’ve managed to keep their union private, sometimes treating us to a quote or two in an interview, or the occasional—but adorable—social media post.
Yet despite keeping it quiet, it’s clear that Oprah and Stedman have a close connection. The key? Respect for one another’s accomplishments. Oprah has often called her significant other “supportive,” and Stedman shares a similar sentiment.
“We want each other to succeed,” he said during a segment on The Oprah Winfrey Show. “And I want her to succeed and to be as successful as she possibly can, so I encourage that.”
But how did this rock-solid relationship happen? Oprah suggests that she manifested Stedman. On an interview with Hoda & Jenna & Friends, she said, “I’d been through a lot of ‘woof woofs.’ You get to the point when you say, ‘No more.’ I actually said, ‘This is what I want. Someone who is kind. Someone who is loyal.’ And that’s what I have.”
To celebrate the moments they have chosen to share with us, from how they met to their engagement and decision not to marry, to supporting each other’s careers, we created a timeline of Oprah and Stedman’s love story, spanning almost 40 years—and counting.
1986: Oprah and Stedman meet for the first time.
The soon-to-be power couple had their meet cute the same year The Oprah Winfrey Show first aired, according to a letter Oprah wrote in O, The Oprah Magazine in 2020. We know that the duo eventually had their happily ever after, but it wasn’t smooth sailing to begin.
“I had seen a particular man around town, but he was always with the same girlfriend, so I didn’t pay much attention,” she wrote. “One day, though, we were both visiting a mutual friend who was ill and later died of AIDS. 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.)”
Apparently, Oprah was a bit wary of Stedman—notably because she deemed his 6'6" frame “too handsome” and thought he would be a player. Her producers were equally as suspicious. (“They figured if he looked like that, he either had to be a jerk or want something,” Oprah told People magazine in 1992.)
But, after cautious consideration—and after she learned he was no longer with the previous girlfriend—Oprah “gave him a serious thought.” And, thankfully, it was a match. “He’s kind and supportive.... Lots of people want to ride with you in the limo. But you want someone who’ll help you catch the bus,” Oprah said in the 1992 People story.
1987: Stedman makes his first appearance on The Oprah Winfrey Show.
During a segment for one of the show’s earliest episodes, Stedman surprised his lady love while she was filming by calling in during a Q&A with viewers. And what did he want to know? What Oprah had been telling her bestie, Gayle King, about him.
“I don’t know if you recognize my voice or not,” he said to a surprised Oprah, who stood in front of her delighted audience.
“Stedman, is that you? Steddy honey?” Oprah replied.
“Yes, baby, how you doin’?” he responded. (Cue the swooning.) “Your friend Gayle—who you talk to about six times a day—every time I see her in person, I’m wondering what she knows about me. I kind of have to look down when I see her, because I don’t know if she knows how many gray hairs I have on my head or what color my toes are.”
As any girlfriend would, Oprah quickly—but lovingly—shot his question down. “Okay, honey. I’ll tell you later, Okay.” And that was that.
So we still don’t know to this day exactly what Gayle knows. But we do know people in high places. Maybe we could ask her....
1992: Oprah and Stedman announce their engagement.
The famously private couple made their engagement public in 1992, with a then 38-year-old Oprah and 41-year-old Stedman opening up to People about his proposal. Here’s how it went down. Gayle and Oprah were at her home waiting for Stedman to bring over a tape of the latest episode of The Oprah Winfrey Show. But when Oprah’s partner finally got there, he popped the big question instead. Apparently, it was a pretty straightforward affair. According to their People interview, Oprah asked, “Is this the proposal?” To which Stedman replied, “I want you to marry me. I think it’s time.” Naturally, Oprah answered, “Ah, that’s really great.”
And while at the time, they planned to get married the following year, a wedding never happened. (More on that later.)
2015: Stedman becomes a grandfather.
Fast-forward a couple decades, and Oprah and Stedman’s relationship is as happy (and private) as ever. And in 2015, that happiness officially extended to a new member of the extended family. The Daily Mail reported that Stedman’s daughter from a previous marriage, Wendy Graham, gave birth to her first child, a girl named Cadence. Neither Stedman nor Oprah has commented publicly about his grandchild, but when we look at how close Oprah and Stedman are with her daughter-girls from her school in South Africa, we can only imagine how loved the little girl is.
2017: Oprah reveals why she and Stedman never got married.
After taking to Twitter in 2016 to address rumors and set the record straight that she and Stedman had never gotten married, Oprah opened up to Vogue about why a marriage between her and her longtime partner would never work. And it turns out the topic is a lot less complicated than it sounds—the subject simply never came up again.
“Nobody believes it, but it’s true,” she said. “The only time I brought it up was when I said to Stedman, ‘What would have happened if we had actually gotten married?’ And the answer is: ‘We wouldn’t be together.’ We would not have stayed together, because marriage requires a different way of being in this world.”
In her 2020 O, The Oprah Magazine letter, she revealed more. “I had doubts. 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.” She continued by writing that he has individual personhood—he isn’t just “Oprah’s man”—and they share the same important values. “And because we relish seeing the other fulfill and manifest their destiny and purpose,” she finished.
January 2018: Oprah and Stedman were each other’s dates at the Golden Globes.
In a rare public appearance, Stedman showed up for his leading lady by accompanying her to the Golden Globe Awards—the year that she gave a rousing acceptance speech (for being the first Black woman to win the Cecil B. DeMille Lifetime Achievement Award, no less) that first inspired the hashtag #Oprah2020 to go viral. Though Oprah did not, of course, run for president in 2020, Stedman chimed in on the support: “It’s up to the people,” he told The L.A. Times in 2018. “She would absolutely do it.”
Later that year, Oprah appeared on Gwyneth Paltrow’s Goop podcast and shared that the reason we don’t see her and Stedman out and about more often is because with every sighting comes “a new photograph...a new story.” (Listen here.)
That low-key lifestyle doesn’t seem to bother Stedman. “We have what a lot of people have who are in a relationship, and we’ve been in a relationship for a long time,” he once said during one (of only three) appearances on The Oprah Winfrey Show. “That’s not always an easy thing to do when you’re a man in a relationship with a very powerful woman, and so I’m not threatened by her fame or her success or all of that, so that’s who she is. It doesn’t have anything to do with how I define myself.”
August 2018: Oprah reveals her perfect date night with Stedman—and it involves black-eyed peas.
While answering questions from readers, Oprah shared a golden answer to one query: What’s a typical date night like for her and Stedman? She didn’t hold back, revealing that the key to her partner’s heart is simple: a home-cooked meal.
“I am a really good cook,” she told us. “My favorite date night is to make him black-eyed peas and cornbread as a surprise for dinner. And then honey—hush. That’s all you need, some black-eyed peas and cornbread. That’s it. Perfect date night. Me cooking and then...it’s on.”
You know if you have Oprah saying, “Honey, hush,” it’s got to be good. Actually...can we get that recipe?
2019: Stedman releases his book Identity Leadership.
Did you know Stedman is actually a New York Times bestselling author? When he penned his 12th book, Identity Leadership, his sweetheart showed her support with an Instagram video of Stedman proudly showing off his newest work. And she wrote a short—but loving—message, complete with her partner’s pet name.
“Honey Graham, I know how much this means to you. Congratulations!”
2020: Oprah and Stedman quarantine together.
During the Covid-19 pandemic, Oprah and Stedman hunkered down in their California home—which naturally led to many isolation-driven antics, like Stedman having to tell Oprah that he ate all of their banana bread or him giving one of Oprah’s daughter-girls a haircut, plus some genuinely wonderful moments, like Gayle’s daughter, Kirby’s, socially distant wedding, which Oprah was happy to host in California.
2021: Oprah and Stedman celebrate many special moments together.
Throughout the year, Stedman and Oprah showed up for each other during occasions like Oprah’s birthday (watch their sweet video here), Thanksgiving (see the delicious South African–inspired spread on Oprah’s Instagram), and Christmas, of course—when they got to meet baby Luca, Kirby’s son, for the first time.
2022: The two continue to support each other as “spiritual partners.”
In the 2020 letter Oprah wrote about her relationship with Stedman, she called what they have a “spiritual partnership.” In 2022, she elaborated on what that means, saying it’s about being truthful, “and the recognition that you’re both in the relationship to grow into who you’re meant to be as individuals as well as as a couple.”
Oprah and Stedman’s year demonstrated this partnership: He was there for Oprah during celebrations like the 68th birthday party she threw for Gayle and the Fourth of July party she threw in honor of her father. And when Oprah’s father passed away later that year, Stedman continued his support behind the scenes.
“He’s appropriately named because he’s steady as a mountain. Even-tempered, accountable, trustworthy, patient,” Oprah says of Stedman.
McKenzie Jean-Philippe is the editorial assistant at OprahMag.com covering pop culture, TV, movies, celebrity, and lifestyle. She loves a great Oprah viral moment and all things Netflix—but come summertime, Big Brother has her heart. On a day off you'll find her curled up with a new juicy romance novel.
Cassie Hurwitz (she/her) is an associate editor at Oprah Daily, where she covers everything from culture to entertainment to lifestyle. She can typically be found in the middle of multiple books and TV shows all at once. Previously, Cassie worked at Parents, Rachael Ray In Season, and Reveal. Her love language is pizza (New York slices, Chicago deep dish, and otherwise).
