Why you so rarely see Oprah with her partner of more than 30 years.

It was 1986 when two very big things happened in the life of Oprah Winfrey.

First, she appeared on a brand new talk show titled The Oprah Winfrey Show. It would go on to become the highest rated daytime program in all of American history.

Second, the 32-year-old attended a charity event in Chicago and met a man named Stedman Graham.

He was handsome, standing at six feet six inches tall, and had recently founded the nonprofit organisation Athletes Against Drugs. 

Graham was established in public relations, and had a degree in social work as well as a master’s degree in education. Three years older than Winfrey, Graham had one daughter from a previous marriage.

It’s widely reported the pair were friends for a time before things developed romantically. And once they did, many of her friends and colleagues were sceptical.

In an interview with People magazine in 1992, Winfrey said: “They figured if he looked like that, he either had to be a jerk or want something”. As time went on, it became clear there was no ulterior motive.

It took almost five years for Graham to leave a toothbrush at Winfrey’s apartment in Chicago. Although they were together, in many respects they led quite separate lives. The Oprah Winfrey Show had become the number-one talk show in the country, and she was heavily involved in humanitarian work.

Winfrey has said that during these years, she let her relationship with Graham take second place to her booming career. But she certainly doesn’t regret it.

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In 1992, reports surfaced that Winfrey and Graham, who had by this point been dating for six years, were engaged.

Winfrey told People magazine that he proposed in the kitchen of their Indiana home. “I want you to marry me. I think it’s time,” he said.

The marriage, however, never eventuated.

At the time, Winfrey was writing a book and Graham said he felt uncomfortable, “having the wedding disturbed by, all these people asking me about it”.

On her podcast SuperSoul Sunday, the media mogul said at the time she wanted Graham to want to marry her.

But once he asked the question, she panicked.

He suggested they postpone the ceremony until the book was finished, and she agreed. Winfrey never released the autobiography, and they never discussed marriage again.


“I realised I don’t want to be married,” she said in the December episode. “… Because I couldn’t have [had] the life I created for myself.”

As well as not getting married, the couple made the choice not to have any children together.

“When people were pressuring me to get married and have children, I knew I was not going to be a person that ever regretted having them, because I feel like I am a mother to the world’s children,” Winfrey told Good Housekeeping UK in early 2017. The philanthropist runs The Oprah Winfrey Academy for Girls in Africa, which has 172 students.

“I didn’t want babies. I wouldn’t have been a good mom for babies,” Winfrey said. “I don’t have the patience.”

Winfrey, now 63, has never spoken publicly about her relationship with her stepdaughter Wendy, who now has children of her own.

In 2013, the media proprietor told News Corp, “If you ever interviewed [Graham], he would tell you that had we married, we would not be together today.

“He’s a traditional man, and this is a very untraditional relationship,” she said.

No HohoHo just A Splashing Christmas our house to yours! ????????????

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Graham has been enormously successful in his own right, publishing several self-help books, two of which are New York Times bestsellers. He is also an educator and podcaster.

Otherwise, Graham has stayed relatively out of the spotlight. “I want her to succeed and be as successful as she possibly can,” he said in a 2015 interview. “That’s not always an easy thing to do when you’re a man in a relationship with a very powerful woman, and so, I’m not threatened by her fame or her success or her money or all of that – that’s who she is. It has nothing to do with how I define myself,” he reflected.

After more than 30 years together, Oprah says she has learned one overwhelming lesson from her decision not to marry.

“Live life on your own terms.”

Listen to the full episode of Mamamia Out Loud.