The Truth About Oprah Winfrey And Stedman’s Relationship

The world seems to know everything about Oprah Winfrey, but fans seem to be even more intrigued when it comes to her partner, Stedman Graham. “I think people are fascinated with the relationship, because you haven’t seen him,” she admitted on her talk show. Most of the time, he’s out of sight. Instead of spending time in the public eye, Graham prefers keeping his life more on the private side.

Why? Well, there’s something about his sweetie, Winfrey. The cameras are constantly following her, her life is plastered across magazine covers, and, sometimes, tabloids like to stir up rumors about their relationship. After all, she’s one of the wealthiest women in the world (via Forbes). Yet, these two stars have always seemed to make their relationship work. “We’re like an old married couple,” Winfrey admitted to People (via Yahoo! News).

This is the truth about Oprah Winfrey and Stedman Graham’s relationship.

Oprah Winfrey and Stedman Graham met through a mutual friend

Oprah Winfrey’s once-upon-a-time began all the way back in 1986 — though it wasn’t love at first sight for Winfrey and Stedman Graham. She had seen Stedman and his girlfriend around town and even noticed him at a charity event in Chicago months before the two ever got close (via People).

One day, Winfrey was over to visit a sick friend when Graham happened to be at the house, too. “I thought he was nice enough,” Winfrey later admitted to O, The Oprah Magazine about her first time meeting him. “But I wasn’t that impressed.” She didn’t think anyone as “handsome” as he was could ever be interested in someone like her.

A few months later, she was surprised to hear about Graham again. Winfrey had obviously wowed him, because he had broken up with his girlfriend and was asking about her all around town. It was then “that I gave him a serious thought,” Winfrey admitted. The rest, as they say, is history.

Oprah Winfrey's producers warned her not to date Stedman Graham

While Oprah Winfrey was slowly falling for a man named Stedman Graham, the people she surrounded herself with were not. At the time, her producers “warned me not to get involved with that Stedman guy,” Winfrey admitted to O, The Oprah Magazine. The same year that this couple met was when Season 1 of The Oprah Winfrey Show first aired. Between Winfrey’s newfound fame and Graham’s good looks, her producers felt that he may be a “player,” which Winfrey admits that she briefly suspected as well. Luckily, this wasn’t the case.

Almost immediately upon dating Graham, the famed talk show host realized that he wasn’t hiding anything at all. “People said when we first started going out that he was after my money or trying to get an acting job,” she explained to the Chicago Tribune of the former sportswear model (via People). “And it was so disheartening because just the opposite was true.”

For their first date, Oprah Winfrey and Stedman Graham went waterskiing

Out of all the things you could do on a first date, Oprah Winfrey and Stedman Graham did something a lot of people don’t. “We went waterskiing,” she told People (via Yahoo! News). It was a pretty daring idea for a first date, but this adventurous encounter was what made Winfrey truly realize what Graham was really like.

Even after falling multiple times, Graham was set on continuing to ski. He was determined to make it back up and out of the water all by himself. “Stedman tried 28 times [to get up] and wouldn’t give up,” Winfrey explained. “I thought, ‘What is wrong with him? Good lord, this is exhausting!’ He would not quit.”

Though Winfrey seemed ready to call it quits on skiing, she ended up appreciating Graham’s determination toward this watersport. Ever since, no matter how many times he falls down, he always gets himself back up, Winfrey shared. “That embodies who he is,” she said.

Stedman Graham has only been to three of Oprah Winfrey's talk show tapings

The Oprah Winfrey Show skyrocketed Oprah Winfrey to success, and over the course of 25 seasons, Stedman Graham played a very supportive role. However, he did it mostly from home. “Stedman has only been to — in my entire career — I think three shows,” Winfrey admitted during a behind-the-scenes video. “So for Stedman to come by a show, it must be, like — extraordinary things must be happening!” Yet, while he likes to keep his distance from the spotlight, during some of her toughest times on air, he’s been on set with her.

He’s been part of fun times, though, too. One year after they began dating, Graham surprised his sweetheart during an episode where viewers were calling in to ask the queen of television questions. “I don’t know if you recognize my voice or not,” he mentioned before continuing with his inquiry. Almost immediately, Winfrey smiled when she realized who it was. 

While Graham didn’t appear much on her daytime talk show, whenever he did, it was a big deal. “You know it’s big if Stedman’s here,” Winfrey said, and fans were fascinated each time he appeared.

Oprah Winfrey and Stedman Graham have been engaged

In 1992, Oprah Winfrey was home watching television with her best friend, Gayle King. They were waiting for Stedman Graham to fly back home from a business trip. When Graham arrived, Winfrey ran outside to greet him, and that’s when he broke some news to her. He had told her, “I want you to marry me,” she explained to People. “I think it’s time.” It was so sudden that she was even unsure if it was sincere. “Ah, that’s really great,” was her reply. However, after six years of dating, he was serious.

Aside from coming back inside to tell her BFF the big news, Winfrey and Graham decided to keep their engagement a secret. However, only a month later, Winfrey revealed it all on a local television show before she was even able to share it with her father. As quickly as she broke the news, however, their engagement was plastered all over national television.

Oprah Winfrey and Stedman Graham had a wedding year set but never got married

Once their engagement news had been spread to everyone in the world, Oprah Winfrey and Stedman Graham planned to tie the knot in 1993. However, they never chose a specific day that year, and they didn’t seem like they were in any rush. “We will announce happily when we’re getting married when we decide, and not before,” Graham announced during an episode of his fiancé’s talk show. He was hopeful this would calm down the fans (via People). 

The year came and went, however, and the celebrity couple never ended up at the altar. While rumors began swirling about their romance, Winfrey decided to share her reservations. “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,” she admitted nearly 30 years later to O, The Oprah Magazine.

Oprah Winfrey and Stedman Graham are grandparents

In 2015, the queen of television got to pick up another pretty great label — grandma. However, you may be wondering exactly how this happened considering Oprah Winfrey and Stedman Graham have never had their own children.

Years before meeting Winfrey, Graham was married to a woman named Glenda. Together, they had a daughter named Wendy. While Graham doesn’t seem to be close with his first wife following their divorce, his daughter has spent a good amount of time with him and Winfrey. Wendy has worked for both of their businesses: Graham’s marketing company and Winfrey’s Harpo Productions. “Oprah has often said she fell in love with Wendy the first day they met and thinks of her as her own daughter,” a source close to her reportedly told Daily Mail.

After Graham’s daughter tied the knot with her own hubby in 2015, she gave birth to a baby girl. Luckily for that little lady, she has some pretty iconic people to now call her grandparents.

Oprah Winfrey and Stedman Graham have debated having children together

While Oprah Winfrey and Stedman Graham don’t have children together, they did briefly debate it. Once they were engaged, Winfrey admitted to People that she “had bought an additional apartment because I was thinking, ‘Well, if we get married, I’m going to need room for children.'”

However, after Winfrey gained success on her daytime talk show, their discussions about children started to dwindle. At work, “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,'” Winfrey said. Motherhood was not something she took lightly, and her time in the limelight made her realize raising children wasn’t her calling.

Though Winfrey and Graham have said they’ll never be parents, they’re still able to act like ones. After opening the Oprah Winfrey Leadership Academy for Girls in South Africa, Winfrey has gotten to spend a lot of time with kids — many of whom have even come to live with her. “Those girls fill that maternal fold that I perhaps would have had,” she admitted. “In fact, they overfill — I’m overflowed with maternal.”

Oprah Winfrey and Stedman Graham's idea of a perfect date isn't anything extravagant

For two celebrities who could fly themselves to any place in the world at any time on their private jet, Oprah Winfrey and Stedman Graham’s idea of the perfect date isn’t as extravagant as we all would think, despite Winfrey’s lavish lifestyle. “We don’t have to go to any special restaurant,” Graham explained to O, The Oprah Magazine. Just like any other couple, spending time together is the ultimate idea. “It’s just having dinner together, because we’re always around a lot of people and she’s very busy, so having quiet time together at home is a beautiful thing,” he added.

Even for these two stars, the simple moments are what they cherish the most. Just eating foods that Winfrey grows in their garden is enough to make it a date night — and that’s the kind that they enjoy the most. “Well, if this isn’t bliss, I don’t know what is,” Winfrey told People.

Oprah Winfrey loves to cook for Stedman Graham

Even if they do happen to have a personal chef, Oprah Winfrey still likes to cook for her sweetie, Stedman Graham. “My favorite date night is to make him black eyed peas and cornbread as a surprise for dinner,” she admitted on Twitter. Surprisingly, it’s something she enjoys doing quite often.

Luckily for Winfrey, her lover appreciates a good home-cooked meal — but only when it’s made by Winfrey herself. “Chefs don’t have anything on her,” he even said in an interview on her website. Graham doesn’t happen to be a picky eater either, so anything goes as long as his lady is cooking.

Over the years, Winfrey has even concocted her own original recipe for him, which they lovingly call “the Love Sandwich.” However, this entreé isn’t only saved for themselves. “I’ve only made it for a couple of other people,” Winfrey said. “So if you’ve had me make the Love Sandwich for you, you have to be somebody I really care about.” After all, the main ingredient is love!

Oprah Winfrey and Stedman Graham like to keep their relationship private

Every bit of Oprah Winfrey’s life is in the spotlight, so her relationship with Stedman Graham is something she likes to keep behind the scenes — and there’s a reason for that. Whenever anything is mentioned about them, rumors begin to run rampant, and frazzled fans have even reached out to them on social media.

In 2016, Winfrey took to Twitter to clear up a massive misunderstanding about their “marriage.” “[Six] people who know me well have called today congratulating me or surprised they weren’t invited to my wedding,” she wrote. “IT’s NOT TRUE!!”

While we all know about Winfrey, many people don’t know much about Graham. He likes to keep it that way. “I don’t think I’d be with him, though, if he didn’t hate the limelight so much,” Winfrey once told the Chicago Tribune, and, clearly, it’s worked out.

As private as their relationship may be, there’s one thing that will probably surprise people about this wealthy celebrity couple. “When you see us, it’s really quite normal,” Winfrey said on her talk show — except, of course, for the fact that they’re one of the most famous couples in the world.

Stedman Graham has always encouraged Oprah to run for president

Oprah Winfrey has admitted again and again that she won’t be running for president anytime soon. It turns out there was someone just behind-the-scenes who was egging her on. Her partner, Stedman Graham, has been the one encouraging her to run for office.

Way back in 1987, only a year after the two started dating, Winfrey admitted to ET that he was the one who wanted to make it happen. “He says to me all the time, ‘Look, I want you to be president,'” she explained, and he’s even volunteered to help run her campaign.

Even from the get-go, Graham has never been intimidated by the amount of success — and the spotlight — that has always followed Winfrey around. “I want her to be the best that she can possibly be,” he admitted in an interview with Ellen DeGeneres. “And she’s done a pretty good job of doing it.” We would have to agree!

Oprah Winfrey and Stedman Graham will never get married

Marriage was not on Oprah Winfrey and Stedman Graham’s minds in 1993, and, it turns out, it never will be. If they had gotten married, “we would not have stayed together,” Winfrey revealed to Vogue. “Because marriage requires a different way of being in this world.”

Not tying the knot has allowed them to create their very own kind of relationship — one that is less traditional, in a sense. As a working woman, Winfrey was not ready to give up her dream of making it on the big screen and settle down. Even after they got engaged, they both seemed to know that their relationship would never morph into a marriage. “My life with the show was my priority, and we both knew it,” she explained to O, The Oprah Magazine.

Between being busy OWNing her own network — pun intended — and traveling all over the world, a wedding will never be in Winfrey or Graham’s plans.

Oprah Winfrey and Stedman Graham have a secret to making their partnership last

There’s a reason why Oprah Winfrey and Stedman Graham have made their romance last, as of this writing, for more than 35 years. “I happen to be with a man who has always appreciated the fact that I was … considered a powerful person,” Winfrey told E! News. “[He’s] not trying to crowd in on it, not competing with it. He knows how to hold his own.”

Since the two travel quite often, they’ve had to learn how to keep their love alive while being millions of miles apart. They’ve made it look easy, too. The “secret” is that their relationship has never been what defines them. Instead, they have their own aspirations. That’s been important for someone as low-key as Graham, who is often referred to as “Oprah’s man.” However, “that’s who she is,” he shared in a behind-the-scenes video at her talk show. “It doesn’t have anything to do with how I define myself.”

The fame and fortune has never gotten to Graham’s head. He’s just someone who’s happened to find the perfect partner for himself. And, like Oprah, we love him for it.

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