Winfrey and Graham, a businessman who has authored several self-help and business-related books, met in 1986 -- the year her now-iconic talk show, The Oprah Winfrey Show, debuted -- at a charity event. Graham was divorced and had a daughter, Wendy. In a January 2020 column for O, The Oprah Magazine, Winfrey recalled meeting him and being wary of his good looks off the bat.
"I thought he was nice enough, but I wasn't that impressed," she wrote of Graham, who's 6 feet, 7 inches tall. "He was polite, yes, and kind. The sort of guy who sits with an ailing friend. Tall and handsome, for sure. But actually too handsome, I thought, to be interested in me. I figured he must be a player. So did all my producers. They warned me not to get involved with that Stedman guy."
"So I proceeded with caution, even with a friendship," she continued. "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."
Graham ended up proving all her friends wrong.
"He's kind and supportive," she told People in 1992, referring to her beau as "my Steddy." "Lots of people want to ride with you in the limo. But you want someone who'll help you catch the bus."
In a February 2020 interview with Hoda Kotb, Winfrey said she had been hoping for someone like Graham before meeting him.
"I did manifest him because I'd been through a lot of 'woof woofs,'" she admitted. "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."
"He's a very special man in that he's not the least bit intimidated by me or what I do," she told ET at the time. "He says to me all the time, 'Look, I want you to be president... you want to be president? Run for president, I'll work on the campaign.' So, I'm very grateful to have somebody like that, who doesn't want to be in the limelight with me, isn't trying-- when you walk into the room, isn't looking for all the cameras. And, so, I don't know what will happen."
After a couple years of dating, the couple already felt the pressure to take the next step in the relationship. In a rare 1989 appearance on The Oprah Winfrey Show, Graham was asked about tying the knot with Winfrey.
"We will announce happily when we're getting married when we decide, and not before," Graham said.
In People's 1992 article, Graham's ex-girlfriend, Chicago television news anchor Robin Robinson, noted that he wasn't one to rush into marriage.
"He's a proud man, and he’s marriage-shy," Robinson said. "The general ill-informed opinion is that Oprah didn't want to marry him. I would question that speculation. He was hurt by his first marriage not working out, and he doesn't like making mistakes."
Still, Graham did pop the question in 1992. Winfrey described his matter-of-fact proposal in her interview with People. Winfrey told the magazine that Graham told her, "I want you to marry me. I think it's time."
Winfrey's reply? "Ah, that's really great."
Of course, the two never did get around to tying the knot. During a 2015 chat with Shonda Rhimes for OWN's SuperSoul Sunday, she admitted she knew immediately that she didn't really wanted to get married, though she did want Graham to propose.
"The moment he asked me to marry him, I was like 'Oh, God! Now I actually have to get married?'" she recalled, sharing that they initially agreed to postpone their wedding -- which was supposed to happen in 1993 -- but then never spoke of it again. "But what I realized is, I don't want to be married. Because I could not have the life that I created for myself ... I knew that I couldn't do it."
"Live life on your own terms," she replied, insisting that marriage was never even an issue she or Graham brought up again after he proposed.
"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. 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."
"The moment after I said yes to his proposal, I had doubts," she wrote. "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. He and I agree that had we tied the marital knot, we would not still be together."
Winfrey has also talked about the pair's decision to not have children together -- though she had previously considered it.
"At one point in Chicago I had bought an additional apartment because I was thinking, 'I'm going to need room for children,'" Winfrey told People in a 2019 interview.
Eventually, she said she didn't have the proper focus to devote to raising a child.
"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 said. "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."
"I have not had one regret about that," she added. "I also believe that part of the reason why I don't have regrets is because I got to fulfill it in the way that was best for me: the Oprah Winfrey Leadership Academy for Girls in South Africa. Those girls fill that maternal fold that I perhaps would have had. In fact, they overfill -- I'm overflowed with maternal."
"I don't think I would have been a good mother for baby children, because I need you to talk to me, and I need you to tell me what's wrong," she bluntly shared. "I can't just figure it out. And I was always -- I knew this about myself. I was always better with kids once they turned 2 and a half, 3. I had a real resonance with them. [My best friend] Gayle [King] was like, 'Don't you love babies?' I was like,'Oh, babies are fine.' … It didn't feel like it was for me."
Winfrey has shared that Graham has never pressured her to fit into the stereotypical wife and mother roles since they weren't married.
"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 told People in her 2019 interview. "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.' 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."
Both 66-year-old Winfrey and 69-year-old Graham insist the reason their relationship has been able to last for so long is because he has his own interests, and he is not defined by just being Winfrey's longtime boyfriend. Graham is definitely successful on his own. He graduated from Hardin-Simmons University with a degree in social work in 1974 and earned a master's degree in education from Ball State University in 1979. He went on to have an extremely successful career in public relations, and one of his clients was the late Maya Angelou.
"Our relationship works because he created an identity beyond being 'Oprah's man,'" Winfrey wrote in her magazine column. "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."
During Graham's recent appearance on The Kyle & Jackie O Show earlier this month, he talked about maintaining his individuality while dating the beloved media mogul.
"I'm defined a lot by my relationship with Oprah, but it has nothing to do with me," Graham said. "That's how you define me! You don't have the tools to define yourself. So, for me, I'm defined a lot by my relationship with Oprah, but it has nothing to do with me."
Graham stressed that focusing on his own interests and path has helped him and Winfrey remain on equal footing all these years.
"That's how you define me, it's not how I define myself, which is why I can maintain the equality with someone who is unbelievable, because I'm not focused on their development as a way to equalize and create freedom," he explained. "I'm focused on my own development. I'm developing a process of continuous improvement every day based on my skills, talents, abilities, purpose and passions. That's what makes me happy."
"So, I don't care what you do," he continued. "I could care less who you are or what you do or what you've been able to accomplish, because it has nothing to do with who I am as a person."
That's not to say that Winfrey and Graham don't proudly support each other's individual accomplishments. When Graham wrote his 12th book, Identity Leadership, which came out last May, Winfrey shared a video of him with a sweet message, revealing one of her pet names for him.
"Honey Graham, I know how much this means to you. Congratulations!" she wrote.
"The thing about our relationship is I want the best for her," he said. "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 it."
"For me, I've been able to find my own happiness, and develop my own skills, my own talents, my own abilities -- and I'm satisfied with that," he added. "So, the combination, when you have a good partner that's able to self-actualize their potential and you're able to self-actualize yours, one and one equals about six."
The couple also has no issue spending time apart and putting themselves first. In March, Winfrey shared that she made Graham quarantine in their guesthouse in Santa Barbara, California, amid the coronavirus pandemic to protect her own health in an interview with Arianna Davis, Oprah Magazine's digital director.
"He's at the guest house, 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," she explained, noting that Graham didn't take the outbreak as seriously as others when it first began, and was initially a bit more cavalier with his travels.
"Stedman did not arrive from Chicago until Thursday, he had been speaking in St. Louis... he'd been on planes," Oprah explained. "So Stedman is like, 'What's the procedure for coming home?' The procedure is… you ain't coming and sleeping in my bed! Literally, he goes, 'I'm not?' And I go, 'Have you not been paying attention to the news? Social distancing does not mean you go and sleep in the same bed with the person! When you just got off American Airlines!' My friends say 'Oh, isn't Stedman upset?' He's really not. He's happy to keep me safe."
"I'm never bored, because I always have myself," she added. "I never feel alone, have never felt alone, because I just love being with myself."
The couple eventually reunited after 14 days, and they lovingly joked on Instagram about their time apart. Although Winfrey has been very private about their relationship throughout these 36 years, both she and Graham have given her fans this type of glimpse into their bond. In 2012, he revealed that Winfrey often cooks for him.
"Chefs don't have anything on her," he told O, The Oprah Magazine about her skills in the kitchen. "Anything she cooks I really enjoy eating, and I appreciate it very much."
She then talked about her famous "Love Sandwich" -- a turkey panini -- that she first started making just for him.
"It became the Love Sandwich because I first started making it just for Stedman," she shared. "I've only made it for a couple of other people, so if you've had me make the Love Sandwich for you, you have to be somebody I really care about."
Graham added, "She makes great pancakes, too. She makes great eggs, she makes great steaks -- I mean, you could go on and on and on. She's just an exceptional cook and an exceptional person."
"One time I tried this, and this was so many years ago, I got this whole negligee thing and I'm standing at the stairs when he comes in, and he literally comes in -- Stedman -- walks right past me and says, 'What are you doing?'" she hilariously recalled in a video with King.
"I've lived, as you have lived, every other week in the tabloids ... It's also why I stopped making as many public appearances with Stedman," she shared. "Because I realized that every time there's a new photograph, there's a new story. It's an invitation."
But perhaps most tellingly about the nature of their relationship and why it works, Winfrey has described their union as a "spiritual partnership" as opposed to a marriage.
"Anyone who's ever met him is always amazed by what a genuine gentleman he is," she gushed about him in her magazine column in January. "He's so positive. Wants the best for me and everyone he knows. Truly wishes people well. Doesn't curse. (I've been known to.) Never have I heard him gossip or say a negative thing about anyone. (I have, plenty of times.) He's appropriately named because he's steady as a mountain. Even-tempered, accountable, trustworthy, patient."
"It's what Gary Zukav defines as a spiritual partnership: partnership between equals for the purpose of spiritual growth," she added of their relationship. "I know for sure it's the ultimate flower on my mind."
For more on Winfrey and Graham's relationship, watch the video below: