Inside the joyful Chicago reunion, rare photos, and why the ultra-private couple still skip the traditional marriage playbook after 40 years together.
ByBernadette Giacomazzo
August 12, 2026
Key Takeaways
- Oprah Winfrey and longtime partner Stedman Graham made a rare public appearance in Chicago at a joyful reunion of The Oprah Winfrey Show staff, nearly 15 years after the show ended and ahead of its 40th anniversary on September 8.
- Together since 1986, the couple has mostly stayed out of the spotlight, with their last major outing dating back to the 2019 opening of Tyler Perry Studios, and Oprah has said she wanted the proposal Graham made in 1992 but not the traditional marriage that came with it.
- The piece also revisits Oprah’s earlier interracial relationship with John Tesh in 1970s Nashville, where the couple faced open racism that they tried to defuse with humor before their careers took them in different directions.
Oprah Winfrey and Stedman Graham have been together for 40 years but actually seeing them out together has become a rarity. That changed over the weekend when Graham joined Oprah in Chicago for a reunion of The Oprah Winfrey Show staff, marking one of the longtime couple’s few public appearances together in recent years.
According to People, the gathering went down at Reunion by Chef Art Smith at Navy Pier, where Oprah reconnected with former staffers 15 years after her groundbreaking daytime show ended its run. Former senior supervising producer Jill Van Lokeren shared photos from the night, calling Graham “the best segment 1 surprise guest” and the celebration a night of “all love and pure joy.”
Oprah also took a moment to put the reunion into perspective: September 8 will mark 40 years since The Oprah Winfrey Show launched. “Thank you for being the greatest team ever,” she told her former crew.
Graham showing up made the occasion even more unusual. Despite having one of entertainment’s longest-running relationships, he and Oprah have largely kept their life together away from cameras. Their last major public outing came nearly seven years ago at the 2019 grand opening gala for Tyler Perry Studios.
Their history goes all the way back to 1986—the same year The Oprah Winfrey Show debuted nationally. Oprah and Graham met at a charity event, became friends, and began dating later that year. Graham proposed in 1992, but the wedding never happened.
Oprah later explained that the engagement forced her to confront what she actually wanted. “I realized I didn’t actually want a marriage. I wanted to be asked,” she wrote in 2020.
She said she wasn’t interested in the “sacrifices, the compromises, the day-in-day-out commitment” she believed a conventional marriage would require.
Before Graham, however, Oprah had another relationship with a man who would eventually become famous on television himself—and their experience together came with a much different set of pressures.
John Tesh revealed years ago that he and Oprah briefly dated while they were young reporters working at competing Nashville TV stations in the 1970s. Earlier this year, Tesh opened up about the racism surrounding their interracial relationship, calling the experience “very uncomfortable back then for an African-American woman and a very, very white guy.”
The hostility was obvious enough that Oprah and Tesh turned it into a running joke. With their schedules allowing them to see each other roughly once a week, Tesh recalled one of them asking, “Hey, which restaurant do you want to empty tonight?”
He also remembered that even then, Oprah stood apart from everyone else in the newsroom. “We all knew that she was something special,” he said.
Tesh confirmed the romance publicly in 2010 after Kitty Kelley’s unauthorized biography of Oprah brought renewed attention to it. The book alleged that racial pressure contributed to a far more dramatic breakup, including claims that Tesh abruptly left their relationship.
Tesh’s own recent account has focused instead on their close friendship, the bigotry they faced, and the careers that eventually sent them in different directions.
Oprah headed from Nashville to Baltimore and ultimately Chicago. Tesh eventually became a fixture on Entertainment Tonight before leaving to pursue music.
