Oprah And Stedman Celebrate “Oprah Winfrey Show” Anniversary: Couple Will Also Celebrate Their 40 Year Anniversary This Year

Oprah Winfrey and her longtime partner, Stedman Graham, made a rare joint public appearance at a star-studded reunion party for The Oprah Winfrey Show staff, marking a double 40-year milestone for both the iconic daytime talk show and their relationship.

The exclusive gathering took place at Chef Art Smith’s restaurant, Reunion, located at Navy Pier in Chicago.

2026 marks two anniversaries for the media mogul and her longtime boo:

The landmark original broadcast of The Oprah Winfrey Show will officially hit its 40th anniversary next month on September 8, 2026, after launching into national syndication in 1986.

And having first met at a charity event in 1986, Winfrey and Graham are simultaneously marking 40 years together as life partners.

The appearance of the longtime celebrity couple stunned attendees and media onlookers alike, as the famously private couple has kept out of the public eye for years. This reunion marked the first time the duo has been photographed together publicly in nearly seven years, with their last shared appearance dating back to October 2019.

Winfrey opted for a casual chic aesthetic, sporting a cream pinstripe blazer paired with white sneakers. Graham complemented her in a classic, tailored black suit. The couple was seen smiling warmly, posing for photographs with Chef Art Smith while holding a large platter of his signature fried chicken.

Their anniversary milestone highlights one of Hollywood’s most enduring and unconventional love stories. Though the couple got engaged in 1992, they famously chose to forgo a traditional marriage.

In a 2020 post to her news diary, Oprah admitted that had she and Stedman pursued the marriage route, the couple may not have stayed together.

“He and I agree that had we tied the marital knot, we would not still be together”, Oprah wrote.

“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). 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.”

Winfrey has frequently stated in interviews that the traditional expectations of being a wife would not have aligned with her demanding career, noting that the freedom of their partnership is exactly what allowed their relationship to survive forty years.