1974: Before meeting Oprah Winfrey, Stedman Graham was married and had a daughter.
The businessman married his first wife, Glenda, in 1974, according to the Daily Mail, but the marriage didn’t last long. Before divorcing, they had one daughter, Wendy, who was born in 1975.
1986: Winfrey and Graham met while visiting a mutual friend who was sick. Winfrey has said she “thought he was nice enough, but I wasn’t that impressed.”
The seeds of Winfrey’s relationship with her longtime beau were planted when they happened to visit a mutual friend who was ill, according to a 2020 article she penned for her O Magazine.
Winfrey knew Graham, a former athlete and sportswear model, had a girlfriend at the time so didn’t put a lot of thought into the idea of dating him. The two left together and she asked him to get a beer but he said he didn’t drink.
“I thought he was nice enough, but I wasn’t that impressed,” Winfrey wrote. “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,” she added.
1986: Later that year, after getting to know each other better, Winfrey and Graham began dating.
Initially, she followed her friends’ advice and maintained a friendship from afar until Graham was single.
“I proceeded with caution, even with a friendship,” Winfrey wrote in the 2020 article. “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 said she soon realized he was “kind and supportive,” months into the relationship, People reported.
“Lots of people want to ride with you in the limo. But you want someone who’ll help you catch the bus,” she added.
1987: Graham began spending more time at Winfrey’s luxury Chicago apartment on the weekends, according to reports.
According to a 1992 People article, when the two began dating, Graham “commuted on weekends from a modest High Point apartment to her lavish condo on Chicago’s Gold Coast.”
At the time, Winfrey was hosting her show, “The Oprah Winfrey Show,” which had launched in 1986. Graham started spending more time in Chicago working with the non-profit he started, Athletes Against Drugs.
1987: He called into Winfrey’s show to ask what she’d been telling her best friend about him.
Graham made his first appearance on “The Oprah Winfrey Show” during a viewer Q&A. He called in to see if Winfrey would dish what she had told her best friend, Gayle King, about their relationship.
“I don’t know if you recognize my voice or not?” Graham said.
“Stedman, is that you? Steddy honey?” Oprah replied.
“Yes, baby, how you doin’?” Graham said. “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.”
A shocked Winfrey quickly ended the phone call, saying, “OK, honey. I’ll tell you later, OK. Thanks for calling.”
1989: As her national profile rose, Winfrey’s personal life, including the question of when she would marry, became the talk of the tabloids.
The couple weathered tabloid storms, including when a Chicago columnist shared a false rumor that Graham was cheating with Winfrey’s hairdresser.
According to the Chicago Reader, the columnist, Ann Gerber, quickly retracted the story and apologized to the couple.
“If I made a mistake,” she said during a press conference, “it was in trying to help Oprah with her pain about the rumor and in agreeing to run a second story.”
October 1992: Graham proposed to Winfrey at her Indiana farmhouse.
According to People, Oprah was hanging in her kitchen with Gayle King and waiting for Graham to get in from Chicago. When Winfrey went outside to meet him after his arrival, he popped the question.
“I want you to marry me,” Graham said. “I think it’s time.”
In response, Winfrey said, “Ah, that’s really great.”
When Winfrey returned to the kitchen, she reportedly told King, “You are not going to believe this, Stedman just proposed!”
The couple kept their engagement a secret for a few weeks, until Oprah shared the news during a November appearance on King’s TV show.
1993: Winfrey and Graham decided not to marry and chose to stay together unmarried.
In her 2020 O Magazine article about her relationship with Graham, Winfrey recalled the immediate joy of being proposed to and then realizing she preferred her relationship with him as it was.
“The moment after I said yes to his proposal, I had doubts,” Winfrey 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.”
1997: Graham opened up to The New York Times about being more than “Mr. Oprah.”
In a 1997 New York Times profile titled, “They Used to Call Me Oprah’s Boyfriend,” Graham opened up about his struggle escaping Oprah’s shadow and how he’s “his own man, with his own ideas and dreams.”
As the founder, president and chief operating officer of S. Graham & Associates — a sports-focused management, marketing, and consulting firm — Graham wanted people and fans of Oprah to recognize him for his own accomplishments.
“People didn’t know anything about what I do or what I’m involved in,” Graham told the Times. ”They say, ‘Wow, where did this guy come from?'”
“I’m stepping out. I know there is going to be a backlash at some point,” he added.
2012: Graham spoke with CNN about what it’s like to be one half of such a highly scrutinized couple.
Speaking to CNN, Graham said he doesn’t base his whole identity off his relationship with Winfrey. He said they each have their own passions and visions that make them individuals.
“I’m with a very special person who is — she’s just so unbelievable, but that has nothing to do with my life. That’s her life. I just support her in her life. And she supports me in my life,” he said.
2017: Winfrey told Vogue that if she and Graham had married, their relationship would not have lasted.
“We would not have stayed together, because marriage requires a different way of being in this world,” Winfrey told Vogue in 2017. “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.”
September 2021: In the new Oprah Daily series “The OG Chronicles: Joy Ride,” Winfrey said that King has been on every vacation with her and Graham since 1993.
Winfrey said that King had vacationed with her and Graham every year since King’s divorce.
“The three of us have had a wonderful time,” King said in the episode. “If I was the third wheel, I didn’t know it! If Stedman didn’t like me, that would’ve been tough.”
Oprah added, “If Stedman didn’t like you, Stedman wouldn’t have lasted. Husbands and boyfriends come and go. Best friends last forever.”
December 2021: Winfrey wrote that Graham calls her COVID-conscious rules “The Policy” in an Instagram post showing their Christmas celebrations.
“Everyone who is spending Christmas at my house has to be vaccinated, boosted, tested, and quarantined,” she captioned an Instagram video showing King’s newest grandchild arriving at her home. “Stedman calls it ‘The Policy’ cause I’m that serious about it.”