Oprah Winfrey and Stedman Graham have been together for four decades, but public appearances as a couple have become increasingly rare. That changed over the weekend when Graham accompanied Oprah to Chicago for a reunion with former The Oprah Winfrey Show staff, marking one of their few outings together in recent years.
According to People, the reunion was held at Reunion by Chef Art Smith at Navy Pier, where Oprah caught up with former colleagues 15 years after her iconic daytime talk show came to an end. Former senior supervising producer Jill Van Lokeren shared photos from the event, describing Graham as “the best segment 1 surprise guest” and calling the evening one filled with “all love and pure joy.”
Oprah also reflected on the significance of the reunion, noting that September 8 will mark 40 years since The Oprah Winfrey Show first premiered. “Thank you for being the greatest team ever,” she told her former staff.
Graham’s appearance made the evening even more special. Although he and Oprah have shared one of Hollywood’s longest-lasting relationships, they’ve kept their personal life largely out of the spotlight. Their last major public appearance together was nearly seven years ago at the 2019 grand opening gala for Tyler Perry Studios.
The couple’s story dates back to 1986—the same year The Oprah Winfrey Show launched nationwide. They first met at a charity event, became friends, and later started dating. Graham proposed in 1992, but the two ultimately decided not to get married.
Looking back on that chapter, Oprah explained that the engagement helped her realize what she truly wanted. “I realized I didn’t actually want a marriage. I wanted to be asked,” she wrote in 2020.
She has also said she wasn’t interested in the “sacrifices, the compromises, the day-in-day-out commitment” she believed came with a traditional marriage.
Before her longtime relationship with Graham, Oprah briefly dated someone who would later become a familiar face on television.
John Tesh revealed years ago that he and Oprah had a short-lived romance while working as young reporters at rival TV stations in Nashville during the 1970s. Earlier this year, he spoke candidly about the racism they encountered because of their interracial relationship, describing it as “very uncomfortable back then for an African-American woman and a very, very white guy.”
The prejudice was so common that the pair eventually joked about it. Since they only had time to see each other about once a week, Tesh recalled one of them asking, “Hey, which restaurant do you want to empty tonight?”
He also said it was obvious even then that Oprah was destined for something bigger. “We all knew that she was something special,” he said.
Tesh first publicly confirmed the relationship in 2010 after Kitty Kelley’s unauthorized Oprah biography renewed interest in their past. The book suggested that racial pressures played a major role in their breakup and included claims that Tesh abruptly ended the relationship.
In more recent interviews, however, Tesh has focused on the friendship they shared, the discrimination they endured, and how their careers ultimately led them down different paths.
Oprah went on to build her legendary career after moving from Nashville to Baltimore and eventually Chicago, while Tesh became a longtime host of Entertainment Tonight before transitioning into music.
