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.