Oprah Winfrey steps out with rarely seen partner Stedman Graham: Here’s what they did

Oprah Winfrey just gave longtime fans a major throwback moment. The television icon made a rare public appearance alongside her longtime partner, Stedman Graham, during a reunion celebrating the legacy of The Oprah Winfrey Show in Chicago. The gathering brought former Harpo Productions employees back together 15 years after Winfrey’s groundbreaking daytime talk show aired its final episode in 2011. 

The celebration also comes at an especially fitting time. The Oprah Winfrey Show launched nationally in 1986, meaning 2026 marks its 40th anniversary. For Winfrey and Graham, the year carries another milestone: the famously private couple have also been together for approximately four decades.

Oprah Winfrey and Stedman Graham Make Rare Public Appearance

Winfrey and Graham attended the gathering at Reunion, chef Art Smith‘s restaurant at Chicago’s Navy Pier. Smith has deep ties to Winfrey’s world. He previously worked as her personal chef and appeared on her talk show, making his restaurant an appropriate setting for a night built around old friendships and shared history. 

Photos from the event showed Winfrey and Graham posing with attendees, including television producer Jill Van Lokeren. Entertainment Weekly reported that Winfrey also spent time with her longtime friend Gayle King and former members of the Harpo Productions family. 

Winfrey dressed in a light cream pinstripe ensemble for the occasion, while Graham opted for a dark suit with a crisp white shirt. 

Oprah and Stedman’s Reunion Appearance Is So Rare

Although Winfrey remains highly visible through interviews, podcasts, productions, and public appearances, Graham generally stays outside the celebrity spotlight.

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According to multiple reports, the Chicago reunion marked the couple’s first major public appearance together in nearly seven years. They were previously photographed at the grand opening of Tyler Perry Studios in Atlanta in October 2019. 

The couple began dating in 1986, the same year The Oprah Winfrey Show entered national syndication. Over the following four decades, Graham has remained a steady figure in Winfrey’s personal life while building his own career as an author, educator and businessman. 

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Their relationship has also famously followed its own rules.

How Long Have Oprah Winfrey and Stedman Graham Been Together?

Oprah Winfrey and Graham have been together since 1986.

They became engaged in the early 1990s but ultimately chose not to marry. Over the years, Winfrey has repeatedly explained that the decision suited both their personalities and their relationship.

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In a 2017 interview, Winfrey said she believed their relationship might not have survived if they had married because traditional expectations surrounding marriage would have changed their dynamic.

Rather than treating marriage as the required destination for a serious relationship, Winfrey and Graham built a partnership that has now lasted roughly 40 years.

© FilmMagic

Graham has similarly spoken about maintaining his own identity while supporting Winfrey’s enormous career. In footage surrounding the final episodes of her talk show in 2011, Graham explained that he wanted Winfrey to be as successful as possible and that he was not threatened by her fame, success, or wealth.

Four decades later, their rare Chicago appearance offered another glimpse at that enduring partnership.