When it comes to love stories that stand the test of time, Oprah Winfrey and Stedman Graham's relationship is in a league of its own. No wedding bells, no grand ceremony—just decades of quiet commitment, personal growth, and deep mutual respect. For nearly 40 years, Oprah and Stedman have been together without ever tying the knot, sparking endless curiosity.
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So, what made Oprah say 'yes' to love but 'no' to marriage?
Who is Oprah's partner of four decades?
Oprah Winfrey met Stedman Graham in 1986 at a charity event, the same year her iconic talk show premiered—where Sussexes made bombshell revelations. At the time, he was known as the handsome man often seen with another woman, which made Oprah and her team suspicious. She wrote for Oprah Daily:
Anybody that good-looking driving a vintage Mercedes merited suspicion.
So I proceeded with caution, even with a friendship.
The two reconnected during a visit to a mutual friend, and Oprah took the leap of asking him out for a beer.
He said he didn't drink. (Still doesn't — not one sip of nothin’ alcoholic since I've known him.)
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.
Soon after, their friendship blossomed into romance. By December that year, they were making their red carpet debut at the Apollo Theatre in New York for the premiere of Native Son.
Described by Oprah as 'steady as a mountain' and a 'genuine gentleman', Stedman has an impressive career in his own right. He is an educator, author, and businessman. His ventures include S. Graham & Associates, and he has written over ten self-help books. According to Hello! Magazine, he also founded a non-profit in Chicago that supports youth education.
Their nearly 40-year bond has been kept largely private, but it's clear from Oprah's reflections that their relationship has thrived because they respect each other's individuality. As Stedman said on The Ellen DeGeneres Show:
Well, the thing about our relationship is, 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 that.
And so for me, I’ve been able to find my own happiness, my own skills, my own talents, my own abilities and I’m satisfied with that. I’m happy with that.
As we peel back the layers of their love story, it becomes clear that their choice to skip marriage was far from a lack of commitment.
Why Oprah never married Stedman – or had children
In 1992, Oprah and Stedman got engaged. However, they called it off the following year. In a candid 2020 essay for Oprah Daily, she explained:
In 1993, the moment after I said yes to his proposal, I had doubts. 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.
In fact, she stated in an interview with Vogue in 2017:
The only time I brought it up [marriage] 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."
Stedman reportedly agreed. According to People, Oprah once said:
Both he and I now say, "If we had married, we would not be together." No question about it.
We would not have stayed together, because marriage requires a different way of being in this world.
Winfrey added:
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.
Their relationship model may defy conventional norms, but it works for them. Oprah describes it as a 'spiritual partnership' – 'partnership between equals for the purpose of spiritual growth.'
Oprah also chose not to have children. In a 2019 interview with People, she admitted ‘the depth of responsibility and sacrifice that is actually required to be a mother’ wasn’t for her. She added:
I never thought that that mothering instinct was something for me. I like babies, but I like them like, 'Hi baby, okay, now go over there.' I like children when they can actually speak to me and tell what is the problem
Despite this, she has found maternal fulfilment through the Oprah Winfrey Leadership Academy for Girls in South Africa. She told People:
They’re the daughters I did not have. They are my greatest, deepest joy.
Was Oprah ever in other relationships?
Before Stedman, Oprah had other relationships, including with someone called Bubba during her Miss Black America pageant days. But none have garnered the same attention as with her current partner. As a matter of fact, one relationship of hers that is probably in the news more than it should is that with Gayle King. Yes, there has been bizarre speculation that their deep friendship could be something more...
Rumours that the two are more than friends have persisted for years, but both have always denied any romantic involvement. As reported by The Independent, Oprah said on a podcast with Melinda French Gates:
For years, people used to say we were gay, and listen, we were up against that forever
King, also part of the podcast, added:
If we were gay, we’d tell you.
She even joked about how the rumours affected her dating life:
I used to say to Oprah: “You’ve gotta do a show on this. Cause it’s hard enough for me to get a date on Saturday night with people thinking we’re gay.”
Oprah believes the speculation stems from the uniqueness of their bond. She said:
Maybe people aren’t accustomed to seeing women with this kind of truth bond.
Their friendship dates back to 1976 when both worked at WJZ station in Baltimore. Through the years, they have supported and celebrated each other unconditionally.
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Sources used:
Hello! Magazine: Who is Oprah Winfrey's partner of almost 40 years? Meet Stedman Graham
People: Oprah Winfrey and Stedman Graham's Relationship Timeline
Oprah Daily: Oprah Explains Why She and Stedman Skipped Marriage for a “Spiritual Partnership”
The Independent: Oprah Winfrey addresses Gayle King relationship rumors
