Oprah Winfrey And Stedman Graham's Love Story, Crossed Paths At Charity And Called Off Wedding Plans

Gayle King has recently responded to the rumours of her romance with Oprah Winfrey. Notably, the talk show host has been in a relationship with Stedman Graham for all these years.

By Anupal Neog Last Updated: May 28, 2026 | 19:12:09 IST

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Oprah Winfrey is in the headlines after Gayle King responded to the reports of her secret romance with the talk show host. Gayle recently appeared on Alex Cooper’s Call Her Daddy podcast on May 27, 2026 (ET), addressing how she reacted to those rumours. Gayle said during the interview that it used to bother her once. She further stated that in case she and Oprah were gay, they would not have hidden the details from anyone.

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For the unversed, Oprah Winfrey has been engaged to Stedman Graham since 1992. The romance started back in 1986. Keep reading to know more about where and how the relationship started!

Oprah Winfrey and Stedman Graham’s first meeting happened at a charity event

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Oprah Winfrey and Stedman Graham’s first meeting dates back to 1986, and they started dating in the same year. The pair attended a charity event, and although Oprah initially had a lot of doubts about Stedman, they met each other once again while visiting one of their friends. Oprah once said in her 2020 essay that she did not pay any attention to Stedman in the beginning because he was “always with the same girlfriend.” She further stated:

“One day, though, we were both visiting a mutual friend who was ill and later died of AIDS. The guy with the girlfriend had come to the friend’s home alone, and so had I. We left together, and I asked if he wanted to get a beer. (Yes, I drank a lot of beer then and wore cowboy boots every day.) He said he didn’t drink. (Still doesn’t - not one sip of nothin’ alcoholic since I’ve known him.)”

Oprah Winfrey started taking Stedman Graham seriously after his split

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As she claimed in her essay, Stedman Graham was romantically linked to someone when Oprah Winfrey met him for the first time. The pair continued to share a close friendship with each other since that period. Situations started to change when Oprah discovered that Stedman and his girlfriend had separated for some reason.

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Apart from that, Graham was reportedly asking about Winfrey’s relationship status, and this is the time when Oprah started reconsidering her thoughts about him. Stedman even shifted to a rented apartment near Oprah’s house at one point. Oprah had once spoken about Stedman in O, The Oprah Magazine, by saying:

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“He’s so positive. Wants the best for me and everyone he knows. Truly wishes people well. He’s appropriately named because he’s steady as a mountain. Even-tempered, accountable, trustworthy, patient.”

Oprah Winfrey and Stedman Graham were in a relationship despite cancelling their engagement

Oprah Winfrey and Stedman Graham’s relationship was going well as they continued appearing together on various occasions. In 1992, the couple got engaged to each other, with Oprah telling PEOPLE that her partner proposed to her when she was at her farmhouse in Indiana. 

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However, the engagement was cancelled in 1993. Oprah opened up on the reasons behind cancelling the engagement in an essay in 2020. She said that she did not want to tie the knot and her only wish was to be asked. Oprah mentioned that although Stedman believed that she was perfect to be a wife, she was not ready for the compromises and commitment that were necessary for the survival of a marriage. 

Oprah Winfrey and Stedman Graham have not exchanged vows until today

While they have been happy together for almost 40 years, Oprah Winfrey and Stedman Graham have yet to tie the knot. Although a rumour related to their marriage emerged in 2016, Oprah later dismissed the claims by sharing a post on X (formerly Twitter). A year after the rumour created headlines, Oprah appeared for another interview with Vogue in 2017, stating that when she once told Stedman about their marriage, he responded by saying that they would not have been together if it had happened. She continued and said:

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“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.”

Back in 2018, Oprah Winfrey opened up on why she has kept her relationship with Stedman Graham away from the limelight. In an interview with Gwyneth Paltrow on the Goop podcast, Oprah said that the false reports emerging about her on different platforms have always been an issue for her. Winfrey stated that this was one of the reasons why she has reduced public appearances with Stedman over the years.

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What are your thoughts about Oprah Winfrey and Stedman Graham’s relationship over the years? Let us know.

Also Read: Travis Kelce Breaks Silence On Fiancee, Taylor Swift Changing Her Name After Their July Wedding

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