
Donald Trump Responds to Allegations Involving Kristi Noem's Husband in Security Probe
April 01, 2026

Oprah Winfrey is one of the most famous people in the world. Several fans even see her as a role model. However, there is one aspect of her life that some followers believe is still incomplete: family.
Those who don’t follow Oprah’s life and career might think that she is single. The truth is that she has been in a relationship with Stedman Graham, an author, educator, businessman, and podcaster, since 1986.

Oprah Winfrey and Stedman Graham at the Wallis Annenberg Center on February 22, 2015 in Beverly Hills, California | Source: Getty Images
Stedman was not the first man in Oprah’s life, though. A filmmaker named Reginald Chevalier told Radar Online that he had a short romance with the host and actress, even claiming that Stedman was the main reason he and Oprah parted ways.
Reginald and Oprah reportedly started dating in 1985, but their romance only lasted four months. The filmmaker, who met Stedman through a gig they worked together, cut ties with him after learning that Stedman was interested in Oprah.

Oprah Winfrey and Stedman Graham at Bacara Resort on December 6, 2014 in Goleta, California | Source: Getty Images
He even pointed out that Stedman used to call Oprah a lot. She allegedly kept telling her then-boyfriend that she didn’t want to talk to Stedman. Reginald added that even though it was a bothering situation, he didn’t do anything because he didn’t want to be “malicious.”
Reginald, who claimed he and Oprah lived together for a while in her Chicago apartment, said that he attended the local premiere of “The Color Purple,” which was her film debut that granted her an Oscar and a Golden Globe nomination.
The way Stedman “stole” Oprah from Reginald was quite uncommon, the filmmaker revealed. He said that Stedman took a girl to a New Year’s Eve party that Oprah threw only to distract him.
Reginald explained that the girl would talk to him every time Oprah was approaching, a strategy to make him look as if they were flirting. Stedman’s plan was successful as Oprah and Reginald broke up soon after that party and started dating.
One of the worst aspects of their supposed break-up was the way she did it: by leaving a note that read, “it’s not going to work out between us.”
Finally, Reginald confessed that Oprah used to talk a lot about marriage and that they would probably be together nowadays had he decided to marry her.
Now, more than three decades after that alleged relationship, Oprah and Stedman are still together, and their romance is growing strong. Some people might consider that their life is somehow incomplete as they have not had any children together.
However, Oprah has never wanted to have them. In an interview with ET, she pointed out that several friends were pressing her to have children and get married, but she always knew she would never be one to regret not doing it.
“I feel like I am a mother to the world’s children… I didn’t want babies. I wouldn’t have been a good mom for babies. I don’t have the patience,” the actress and host revealed.
In a different conversation she had with Vogue, Oprah revealed that neither Stedman nor Oprah brought up the marriage topic in their relationship and that not being married was one of the keys to their successful bond.
“Nobody believes it, but it’s true. The only time I brought it up 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,’” admitted the actress.
Later, Oprah added that the reason they wouldn’t be together was that marriage required “a different way of being in this world.” She said that she wouldn’t fit into the traditional wife role that Stedman interprets when it comes to marriage.
Several people, including her friend Tina Turner, have tried to convince her to get married many times, but she has refused every single one.
However, in 2016 netizens created a rumor claiming that she and Stedman were engaged. The rumor was so popular that Oprah herself took to Twitter to shut it down.
“6 people who know me well have called today congratulating me or surprised they weren't invited to my wedding. IT' s NOT TRUE!!”
At the moment, Oprah and Stedman have been together for more than three decades, and they are very unlikely to tie the knot anytime soon.

Donald Trump Responds to Allegations Involving Kristi Noem's Husband in Security Probe
April 01, 2026

Jane Fonda, 88, Stuns at TCM Gala, Sparks Reactions Over Her Handsome Son — Photos
May 14, 2026

Kristi Noem's Marriage Faces Scrutiny After Reports on Husband and Affair Rumors
April 02, 2026

Mel C, 52, Marries in a Backless Wedding Gown — but One Famous Name Missing from the Guest List — Photos
July 21, 2026

Kevin Hart Sparks Reactions with Awkward Party Footage — Video Goes Viral
May 25, 2026

Public Has Mixed Reactions After Goldie Hawn Reveals Her True Marriage Views with Kurt Russell
May 11, 2026

New Jersey Woman's Chilling 911 Call Reveals Shocking Family Crisis
May 01, 2026

Princess Diana's Brother Charles Spencer Marries a Woman the Same Age as Prince William – See Wedding Photos
May 20, 2026

Justin Fairfax's Final Days Hide Disturbing Details About Family Money and Looming Deadline
April 17, 2026

Mark Harmon and Pam Dawber's Decades-Long Marriage Endured Five Major Life Struggles — Photos
July 16, 2026

Supermodel Paulina Porizkova, 61, Marries Comedy Writer Jeff Greenstein in Italy in a Custom Couture Gown in a Surprising Color — Photos
July 17, 2026