Oprah Winfrey and Stedman Graham's Relationship Timeline

Oprah Winfrey and Stedman Graham first met at a charity event in 1986

Oprah Winfrey and Stedman Graham have been together for over 35 years.

The couple first met at a charity event in 1986, the same year The Oprah Winfrey Show premiered. After striking up a friendship, the pair eventually started dating later that year. While they were engaged at one point, Winfrey and Graham decided to forgo marriage in exchange for a different kind of life partnership.

During an appearance on The Ellen Degeneres Show in May 2019, Graham opened up about how he and Winfrey have maintained a successful relationship by having their own identities.

“Well, the thing about our relationship is, so I’m dedicated to her happiness, so that’s great for her and I want her to be the best she can possibly be and she’s done a pretty good job of doing that,” he said. “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. I’m happy with that.”

Winfrey has also defined her decades-long relationship with Graham as “spiritual partnership,” a term coined by author Gary Zukav. She explained in a 2020 issue of her magazine, “Partnership between equals for the purpose of spiritual growth."

Related: Oprah Winfrey Reveals How She and Stedman Graham Have Made Their 'Spiritual Partnership' Work

From why they chose not to get married to the milestones they’ve celebrated together, here’s everything to know about Oprah Winfrey and Stedman Graham’s relationship.

1986: Oprah Winfrey and Stedman Graham first meet at a charity event

Winfrey and Graham first met at a charity event in 1986, but she was initially skeptical about the businessman. In an essay she wrote for O, The Oprah Magazine in 2020, Winfrey revealed they reconnected that same year while visiting a mutual friend.

“I had seen a particular man around town, but he was always with the same girlfriend, so I didn’t pay much attention,” she said. “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.)”

Winfrey said she “thought he was nice enough,” but she and her producers were wary that he was “too handsome” and that he “must be a player.”

1986: Oprah Winfrey and Stedman Graham begin dating

Despite her suspicions, Winfrey struck up a friendship with Graham. “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,” she wrote for her eponymous magazine in 2020.

At the beginning of their relationship, Graham would commute to Winfrey’s condo in Chicago and eventually rented his own apartment just a few blocks away from her home. In 1992, Winfrey told PEOPLE it had only been in the last year that Graham “keeps a toothbrush at my apartment.”

While Winfrey initially was unsure about Graham, she said in O, The Oprah Magazine that the businessman was a “genuine gentleman.”

“He’s so positive. Wants the best for me and everyone he knows. Truly wishes people well,” she wrote. “He’s appropriately named because he’s steady as a mountain. Even-tempered, accountable, trustworthy, patient.”

December 8, 1986: Oprah Winfrey and Stedman Graham make their red carpet debut

By December 1986, Winfrey and Graham weren’t shy about taking their romance public. They attended the premiere of Native Son at the Apollo Theatre in New York City together and were photographed holding hands. Winfrey starred in the drama film as the character Mrs. Thomas.

1987: Stedman Graham makes an appearance on The Oprah Winfrey Show

A year into their relationship, Graham made his first appearance on The Oprah Winfrey Show. During a Q&A segment with viewers, Graham surprised Winfrey by calling in to ask her what she had been telling her best friend, Gayle King, about him. The TV host immediately recognized his voice, calling him “Steddy honey.”

“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,” Graham said in the segment. “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.”

Winfrey laughed and quickly shot down the question. “Okay, honey. I’ll tell you later,” she said.

October 1992: Oprah Winfrey and Stedman Graham get engaged

After six years of dating, Winfrey and Graham got engaged in October 1992. A month later, the couple opened up about the proposal in a cover story for PEOPLE. Winfrey said she was at her Indiana farmhouse with King when Graham arrived and popped the question after she went outside to greet him.

According to Winfrey, she asked, “Is this the proposal?” to which Graham replied, “I want you to marry me.”

1993: Oprah Winfrey and Stedman Graham call off engagement

Winfrey and Graham chose to call off their engagement in 1993 but remained a couple. In her 2020 essay, Winfrey revealed that she started having doubts as soon as she accepted Graham’s 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 added, “He and I agree that had we tied the marital knot, we would not still be together.”

Related: 'Don't Need a Paper to Be Devoted': What Stars Have Said About Choosing Not to Marry

May 15, 1998: Oprah Winfrey thanks Stedman Graham in her Daytime Emmy Awards acceptance speech

In 1998, Winfrey won the Lifetime Achievement Award at the Daytime Emmy Awards. She thanked Graham in her emotional acceptance speech while mentioning those who had “nurtured” her.

"Stedman, you're the sweetest man, with the greatest integrity," Winfrey said as the camera showed a tearful Graham. "Thank you for helping me to be everything that I am, and all that is to come."

September 22, 2002: Oprah Winfrey and Stedman Graham attend the Primetime Emmy Awards

Winfrey and Graham attended the Primetime Emmy Awards together on Sept. 22, 2002. The TV host took home the first-ever Bob Hope Humanitarian Award and once again mentioned Graham in her acceptance speech.

While talking about how everyone wants to “find somebody to love,” she paused and said, “Stedman, thank you.”

2011: Stedman Graham says he’s “not threatened” by Oprah Winfrey’s success

In a behind-the-scenes video from Winfrey’s last few episodes of The Oprah Winfrey Show, Graham made an appearance to support his longtime partner. Winfrey mentioned in the video that “people are fascinated with the relationship” because they “haven't seen him.”

"We want each other to succeed. And I want her to succeed and be as successful as she possibly can, so I encourage that,” Graham explained in the video. “That's not always an easy thing to do when you're a man in a relationship with a very powerful woman. So I'm not threatened by her fame or her success or her money."

September 2016: Oprah Winfrey shuts down rumors she married Stedman Graham

After a report claimed that Winfrey and Graham had secretly married in September 2016, the media mogul took to X (formerly Twitter) to set the record straight.

“Six people who know me well have called today congratulating me or surprised they weren’t invited to my wedding,” she wrote in the tweet. “It’s not true!!”

August 2017: Oprah Winfrey opens up about why a marriage with Stedman Graham wouldn’t have lasted

Winfrey talked to Vogue in August 2017 about why marrying Graham was never a serious consideration despite their 1992 engagement.

“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.”

Winfrey added, “His interpretation of what it means to be a husband and what it would mean for me to be a wife would have been pretty traditional, and I would not have been able to fit into that.”

January 7, 2018: Oprah Winfrey and Stedman Graham attend the Golden Globe Awards

Graham was on hand to support Winfrey at the Golden Globe Awards on Jan. 7, 2018, when she accepted the Cecil B. DeMille Award. At the beginning of her acceptance speech, the media mogul mentioned Graham as someone “who’s been my rock.”

March 2018: Oprah Winfrey explains why she keeps her relationship with Stedman Graham private

Winfrey and Graham are a very private couple, and The Color Purple star opened up to Gwyneth Paltrow on her Goop podcast about why they keep their relationship out of the spotlight.

Winfrey shared that she was often bothered by the number of untrue stories about her in the media and even sought advice from Maya Angelou. “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,” she said.

August 2018: Oprah Winfrey reveals her “perfect date night” with Stedman Graham

During an O, The Oprah Magazine’s "Ask a Staffer" Q&A on Instagram in August 2018, Winfrey shared that Graham is always game to eat whatever she cooks for him.

“Well, I am a really good cook and the wonderful thing about Stedman is in all the years that I’ve been cooking for him, no matter what it is — even if it’s a piece of toast — like the other day I made an English muffin and he’s like, ‘Where did you get this English muffin?’ and I’m like, ‘It’s an English muffin,' ” she said.

Winfrey also revealed the meal she cooks for Graham on her idea of a “perfect date night.”

“He is delighted with anything that I make, so my favorite date night is to make him black-eyed peas and cornbread as a surprise for dinner, and then, honey, hush,” she said. “That’s all you need. A little black-eyed peas and corn bread. That’s it!”

October 2019: Oprah Winfrey explains why she chose not to marry or have children

In an October 2019 interview with PEOPLE, Winfrey shared that she has no regrets about not getting married or having children. The A Wrinkle in Time star explained that while she had considered becoming a mother after she and Graham got engaged, she soon realized “the depth of responsibility and sacrifice that is actually required to be a mother.”

Winfrey said she didn’t “have the ability to compartmentalize,” which is also one of the reasons why she never tied the knot with Graham.

“I used to think about this all the time, that I was working these 17-hour days, and so were my producers, and then I go home and I have my two dogs and I have Stedman, who’s letting me be who I need to be in the world,” she said. “He’s never demanding anything from me like, ‘Where’s my breakfast? Where’s my dinner?’ Never any of that, which I believed would have changed had we married.”

With over 30 years of partnership, Winfrey told PEOPLE she and Graham stand by their decision to call off their engagement. “Both he and I now say, ‘If we had married, we would not be together,' ” she said. “No question about it — we would not stay married, because of what that would have meant to him, and I would have had my own ideas about it.”

Winfrey does consider the students and alumnae of students and alumnae of the Oprah Winfrey Leadership Academy for Girls, a South African boarding school she opened in 2007, her "daughters."

“They are my greatest, deepest joy,” she told PEOPLE in 2019. "They’re the daughters I did not have. I never thought that that mothering instinct was something for me. I like babies, but I like them like, ‘Hi baby, okay, now go over there.’ I like children when they can actually speak to me and tell what is the problem. This is how having children was supposed to manifest for me.”

January 2020: Oprah Winfrey discusses how she and Stedman Graham make their “spiritual partnership” work

In her 2020 essay for O, The Oprah Magazine, Winfrey referred to her relationship with Graham as a “spiritual partnership.” She explained that she learned the term from author Gary Zukav, and it means a “partnership between equals for the purpose of spiritual growth.”

As for how they’ve made their partnership work for decades, Winfrey said it’s “because he created an identity beyond being ‘Oprah's man’ (he teaches Identity Leadership around the world and has written multiple books on the subject). And because we share all the values that matter (integrity being number one). And because we relish seeing the other fulfill and manifest their destiny and purpose.”

March 2020: Oprah Winfrey and Stedman Graham quarantine together

When the COVID-19 pandemic hit in March 2020, Graham had been traveling for work. When he returned, Winfrey initially had him quarantine by himself in the guest house.

“He’s at the guesthouse, because you all know I had pneumonia late last year ... I had just gotten off of antibiotics last week, because I had a bronchial infection,” Winfrey said in an Instagram Live. “Stedman did not arrive from Chicago until Thursday, he had been speaking in St. Louis ... he’d been on planes, so Stedman is like ‘What’s the procedure for coming home?’ The procedure is ... you ain’t coming and sleeping in my bed!”

The pair reunited a few weeks later and spent the rest of the pandemic quarantining together. In May 2020, Winfrey shared a photo of her and Stedman doing a puzzle together on Instagram.

“Never in a million years did I see me and @stedmangraham doing a puzzle on a weekday night,” she captioned the photo. “But after two months in quarantine, we’ve had to figure out different ways to spend time together.”

January 29, 2021: Oprah Winfrey and Stedman Graham spend her 67th birthday together

Winfrey and Graham celebrated her 67th birthday with a cozy day at home. She shared a video of the businessman singing her “Happy Birthday” while they prepared to cut into a two-tiered yellow cake.

“Thank you to all my special friends, and friends I didn’t even know I had, for your birthday wishes! I felt blessed by your messages. And grateful to have another turn around the sun,” she wrote in the caption. “@stedmangraham and I had a quiet day at home watching The Autobiography of Miss Jane Pittman and Sounder and ate some cake.”

December 2023: Oprah Winfrey reveals the obscure breakfast food she keeps in the fridge for Stedman Graham

While appearing on the cover of PEOPLE in December 2023, Winfrey shared the strangest thing she keeps in her refrigerator: octopus.

“Stedman likes it for breakfast,” she said, adding that the mollusk sits in their fridge whole on a “regular basis" and Graham is the "only one who eats it."

“The tentacles and the head are there. He likes it seared [or] sautéed with okra and greens,” Winfrey added.

April 11, 2024: Oprah Winfrey talks about aging for PEOPLE's 50th anniversary issue

Though Winfrey didn't mention Graham in her April 2024 interview with PEOPLE, she did open up about how "grateful" she is for what she has in her life at 70.

"When you’re grateful for what you have, you end up seeing you have more than you imagine," she said. "Start with your breath, and recognize what an absolute miracle it is that your heart’s still pumping. That is a revelation to me every day. I’m grateful for it all."

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