Oprah Winfrey reveals why she won’t tie the knot with her longtime boyfriend of +35 years

Oprah Winfrey and Stedman Graham have been a power couple for over 35 years, but despite their deep love, they’ve never walked down the aisle.

Curious about why they’ve chosen to remain unmarried?

Here’s Oprah’s candid explanation for their surprising decision:

First date

1986 was a landmark year for TV icon Oprah Winfrey. Her legendary show, The Oprah Winfrey Show, premiered, and that same year, she met the love of her life, Stedman Graham.

Their first encounter took place at a charity event, but it wasn’t love at first sight. Instead, the two began a friendship.

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

At first, the media referred to Stedman as Oprah Winfrey’s “gentleman friend.” Stedman Graham, from Chicago, was then the head of Athletes Against Drugs.

A year later, it became clear that the couple was indeed together, and their relationship was officially recognized.

”We hung out together. We traveled in the same circles and we were always kind of eyeing each other, so to speak. Then we became available to date and so we did. We went on a casual date to the theater. No big thing. it was nice. We had a good time,” Stedman told The Palm Beach Post.

Even in 1987, entertainment reporters were already speculating about when a wedding might happen. However, Stedman wasn’t particularly keen on discussing marriage. Instead, he praised his new girlfriend, calling their relationship the most “refreshing” he had ever experienced.

Though Stedman had a successful career of his own, he didn’t mind being known as Oprah Winfrey’s partner.

However, he made it clear he didn’t want to be referred to as “Mr. Winfrey”.

”I basically know where I’m going. I’m proud of her. If she wants to run for president, I would encourage her. People have a lot of respect for me because I try to be independent. I don’t try to associate myself with her,” Stedman once explained.

Getting engaged

In 1992, Oprah Winfrey announced her engagement to Stedman. It was Stedman who finally popped the question, after visting Oprah at her Indiana farmhouse.

”It does scare me a little bit, the whole idea of being married to somebody for the rest of your life”, the media billionaire said in an interview with WFSB-TV. 

”You don’t want to wake up 10 years from now and say, ’My God’, who is this I’ve married+’. So sit scares me a little bit, but I think it’s the right thing to do.”

No wedding date was set and in the end, the couple never walked down the aisle. In 1993, they called off the engagement.

“I realized I didn’t actually want a marriage. I wanted to be asked,” she wrote for the O, The Oprah Magazine in 2020 and continued:

“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.”

At the same time, there was no doubt that Oprah truly adored Stedman. 

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

Stedman also realized that marriage might not have been the best choice for the couple. He agreed that if they had gotten married, they likely would not still be together today.

“Nobody believes it, but it’s true,” Oprah wold Vogue in 2017.

“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.”

Oprah Winfrey kids

During one period of their relationship, Oprah considered having children. After getting engaged to Stedman, she admits she thought about it.

“At one point in Chicago, I had bought an additional apartment because I was thinking, ‘Well, if we get married, I’m going to need room for children,’” the media mogul said.

But she and Stedman concluded that it wasn’t the right choice for them at that time. After interviewing many married mothers on The Oprah Winfrey Show, she realized that motherhood requires serious responsibility and “sacrifice.”

Because of that, she holds mothers in the “highest regard” – but she doesn’t look back and wonder about what might have been.

“I realized, ‘Whoa, I’m talking to a lot of messed-up people, and they are messed up because they had mothers and fathers who were not aware of how serious that job is,’” she explained.

“I don’t have the ability to compartmentalize the way I see other women do. It is why, throughout my years, I have had the highest regard for women who choose to be at home with their kids, because I don’t know how you do that all day long. Nobody gives women the credit they deserve.”

Why they are a very private couple

Oprah Winfrey and Stedman Graham have lived their lives in the spotlight, but they’re known for keeping their relationship quite private.

Oprah has joked about how little people know about what Stedman looks like, but in reality, they have attended many premieres and galas together.

Lately, Oprah has been steering clear of public appearances with Stedman to avoid the constant speculation and rumors that often come with them. For instance, in 2016, there was a buzz that the couple had secretly married, which led Oprah to publicly refute the rumors.

“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!!”

The perfect date

Today, Oprah refers to her relationship with Stedman as a “spiritual partnership.” Occasionally, the TV star shares intimate details about her life with Stedman, like what she considers the perfect date with 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,’ ” Oprah revealed during an Q&A on Instagram.

“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!”

Why they never married

So, to circle back to the original question of why Oprah and Stedman never married—after many years and numerous discussions on the topic, the picture is quite clear.

Oprah has repeatedly shared that she doesn’t believe marriage is the right choice for her and their relationship. Despite their deep connection and commitment to each other, Oprah feels that their current arrangement is what works best for them.

“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.”

”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.”

Oprah and Stedman’s relationship is a testament to the fact that love and commitment don’t always follow conventional paths.

Their journey together highlights that it’s perfectly okay to define your own relationship on your own terms, finding fulfillment and happiness in the way that suits you best – share this story if you agree!