10 Sweet Photos of Oprah Winfrey and Stedman Graham’s Decades-Long Relationship

Samantha StutsmanWed, August 12, 2026 at 10:00 AM UTC

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Oprah Winfrey and Stedman Graham in 1989; Oprah Winfrey and Stedman Graham in 2019.Credit: Vinnie Zuffante/Getty; Prince Williams/Wireimage

Oprah Winfrey and Stedman Graham have built a lasting partnership on their own terms.

The pair met at a charity event in 1986, the same year The Oprah Winfrey Show made its debut. Though they later got engaged, Winfrey and Graham ultimately chose not to walk down the aisle — a decision Winfrey has credited with helping their relationship thrive over the past 40 years.

“He and I agree that had we tied the marital knot, we would not still be together,” she wrote in a January 2020 issue of Oprah Daily.

Instead, Winfrey has described what she and Graham share as a “spiritual partnership,” borrowing a term from author Gary Zukav.

“Our relationship works because he created an identity beyond being ‘Oprah’s man.’ ... And because we share all the values that matter (integrity being number one),” Winfrey wrote. “And because we relish seeing the other fulfill and manifest their destiny and purpose.”

Here’s a look back at Oprah Winfrey and Stedman Graham’s romance in photos.

01 of 10

An Emmy Night to Remember

Stedman Graham and Oprah Winfrey attend the 21st annual Daytime Emmy Awards.Credit: Vinnie Zuffante/Getty

In May 1994, Graham joined Winfrey at the 21st annual Daytime Emmy Awards in New York City. That evening, she won the awards for Best Talk Show Host and Best Talk Show.

02 of 10

Oscars Date Night

Oprah Winfrey and Stedman Graham at the 67th Academy Awards.Credit: Barry King/Liaison via Getty

Winfrey and Graham stepped out in style for the 67th annual Academy Awards in Los Angeles in March 1995. Nearly a decade earlier, Winfrey had earned her first Oscar nomination for her performance in The Color Purple.

03 of 10

Red Carpet Romance

Steadman Graham and Oprah Winfrey attend the New York premiere of “Beloved” in 1998.Credit: Ron Galella, Ltd./Ron Galella Collection via Getty

Graham was by Winfrey’s side for the N.Y.C. premiere of Beloved in November 1998. Based on Toni Morrison’s Pulitzer Prize-winning novel, the film starred Winfrey alongside Danny Glover.

04 of 10

Having a Ball

Oprah Winfrey and Steadman Graham at the Governors Ball following the 54th annual Primetime Emmy Awards in 2002.Credit: Frank Micelotta/ImageDirect via Getty

After the 54th annual Primetime Emmy Awards in September 2002, Winfrey and Graham celebrated at the Governors Ball. Earlier that evening, Winfrey was honored with the Bob Hope Humanitarian Award for her philanthropic efforts.

05 of 10

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A Capital Celebration

Oprah Winfrey and Stedman Graham at the 2010 Kennedy Center Honors Artists’ Dinner.Credit: Ron Sachs/Pool via Bloomberg/Getty

Graham proudly supported Winfrey throughout the 2010 Kennedy Center Honors festivities in Washington, D.C., where she was celebrated alongside Merle Haggard, Bill T. Jones, Paul McCartney and Jerry Herman.

06 of 10

Ready for Their Close-Up

Oprah Winfrey and Stedman Graham at the 87th annual Academy Awards.Credit: Dan MacMedan/WireImage

Winfrey brought Graham along for another glamorous Oscars date night in February 2015. The couple attended the 87th annual Academy Awards, where Selma — which starred Winfrey as civil rights activist Annie Lee Cooper — was nominated for Best Picture.

07 of 10

Forever Valentine

Oprah Winfrey and Stedman Graham in 2016.Credit: Oprah Winfrey Instagram

On Valentine’s Day in 2016, Winfrey and Graham were guests at Liberty Ross and Jimmy Iovine’s wedding in Malibu, Calif.

“Stepping out with my Valentine of almost 30 yrs!” the TV host wrote on Instagram alongside a photo of her and Graham embracing.

08 of 10

A Golden Night

Stedman Graham and Oprah Winfrey attend the 75th annual Golden Globes in 2018.Credit: Michael Kovac/Getty

Graham was there to cheer on Winfrey at the 75th annual Golden Globe Awards in January 2018, where she made history as the first Black woman to receive the Cecil B. DeMille Award.

09 of 10

Piece by Piece

Stedman Graham and Oprah Winfrey in May 2020.Credit: Oprah Winfrey/Instagram

During the COVID-19 lockdown in 2020, Winfrey and Graham found creative ways to pass the time at home together — including tackling a puzzle.

“Never in a million years did I see me and @stedmangraham doing a puzzle on a weekday night,” Winfrey wrote on Instagram. “But after two months in quarantine, we’ve had to figure out different ways to spend time together.

10 of 10

A Very Oprah Reunion

Chef Art Smith, Oprah Winfrey and Stedman Graham in 2026.Credit: jvanlokeren/Instagram

Graham joined Winfrey as she reunited with former The Oprah Winfrey Show staffers at Chicago’s Navy Pier in August 2026, ahead of the show’s 40th anniversary.

“I cannot even believe that as of next month, September 8, it will be 40 years since we first launched The Oprah Winfrey Show,” Winfrey told the crowd. “Thank you for being the greatest team ever.”

on People

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Source: “AOL Entertainment”