Oprah Winfrey’s Boyfriend: All About Stedman Graham & Their 38-Year Relationship

Oprah Winfrey, 69, is a household name, author, and media powerhouse! The Color Purple star has gone on to win multiple Emmy Awards, along with countless prestigious nominations. Fans will be able to watch Oprah at the 81st Golden Globe Awards on January 7, 2024, as she is set to present along with other A-listers.

Although the 69-year-old is not nominated this year, the 2023 version of The Color Purple is up for awards for specific actors including the Best Performance by a Female Actor in a Supporting Role in any Motion Picture award and the Best Performance by a Female Actor in a Motion Picture – Musical or Comedy award. Although it’s unclear if Oprah will be walking the red carpet with a plus one, below is everything to know about her leading man!

Oprah Winfrey’s Boyfriend, Stedman Graham

The What I Know For Sure author has been in a long-term relationship with educator and businessman, Stedman Graham, 72, for many decades. Oprah and her man first met in 1986 when they both attended the same charity event, as reported by PEOPLE. They initially had a platonic relationship, but later sparked a romance that same year.

By 1992, the lovebirds officially made plans for their future and became engaged to be married. Stedman asked Oprah to marry him during a visit to her farmhouse in Indiana. Despite the pre-nuptial bliss, Oprah and the now 72-year-old called off their engagement in 1993. The TV personality opened up about the end of the engagement in her 2020 essay in Oprah Daily.

“For years, there were hundred of tabloid stories, weekly, on whether we would marry. In 1993, the moment after I said yes to his proposal, I had doubts. I realized I didn’t actually want a marriage,” she penned at the time. “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.”

Is Oprah Winfrey Married?

Although Stedman and Oprah ended their engagement, they remained together, however, they opted to not get married. “He and I agree that had we tied the marital knot, we would not still be together,” she wrote in the same essay mentioned above. The billionaire also revealed why their romance continues to succeed decades after they called off their “I Dos.”

Oprah admitted that Stedman’s career and life separate from hers is the secret to their successful romance. “Our relationship works because he created an identity beyond being ‘Oprah’s man’ (he teaches Identity Leadership around the world and has written multiple books on the subject),” she explained in the essay. “And because we share all the values that matter (integrity being number one). And because we relish seeing the other fulfill and manifest their destiny and purpose.” Rather than a traditional marriage, Oprah opted for a “spiritual partnership” with Stedman.

What Oprah Winfrey Has Said About Her Relationship

Even though the A Wrinkle in Time star lives a very public life, she often keeps the details of her romance out of the spotlight. Despite this, she still gushes over Stedman every now and again. Oprah doesn’t share photos with Stedman on social media too often, but she did share an adorable portrait with him for Valentine’s Day in 2016. “Stepping out with my Valentine of almost 30 yrs!” she penned in the caption of the post.

Most recently, in December 2023, Oprah opened up during an appearance on The Drew Barrymore Show and revealed what the “most” romantic thing Stedman has done for her is. She explained that over the years, they had four out of five of their dogs pass away and that her boyfriend would have each of the late pets write a Valentine’s Day card for her. “Each of the dogs would send their own bouquet. That’s the most romantic,” she gushed.