The 65-year-old billionaire mogul opens this week on the issue of not marrying and not having children, celebrating extraordinary women in a changing world.
Winfrey, who met her longtime partner Sted Man Graham at a charity event in 1986, tells PEOPLE that she once thought about becoming a mother and 68-year-old Graham being engaged.
Winfrey says, "On a Chicago occasion, I bought an extra apartment because I was thinking, 'Well, if we get married, I'll need room for children.'
While that has never happened, Winfrey said she had seen the "depth of responsibility and sacrifice" that she needs to be a mother during her years at the Oprah Winfrey Show.
"I realized, 'Yeah, I'm talking to a lot of messy people, and they messed up because their mothers and fathers didn't know how serious the job was." I can't compartmentalize the way I see other women do. It is why, during my years, I have had the highest admiration for women who prefer to be at home with their children, because I don't know how you do that all day long. Nobody gives women the credence they deserve.
She continues, "I kept thinking about it all the time, that I was working those 17 hours, and so my producers, and then I went home, and I had my two dogs, and I had Stedman, who lets me live, I need to be in the world. He never asks for anything, like where is my breakfast? Where is my food? 'I wasn't sure if we would get married. "
"We both now say, 'If we had married, we would not stay wedded,'" she adds. "No enigma about it — we would not stay wedded because of what that would ought implied to him, and I would have had my impressions about it."
It is a decision that goes with it.
"I have never regretted it. I also admit that one of the reasons I didn't regret it was that I accomplished it in the policy that was best for me: the Oprah Winfrey Leadership Academy for Girls for South Africa, "she says." Maternity recruits that I probably got. They fill up - I suffer from maternity. "
For the remaining five moments that changed Winfrey's life - including what she says about her relationship with Stedman Graham.