This article was originally published on Crafting Your Home. A human contributor also wrote and edited the post.
Oprah Winfrey does not make many public appearances with her longtime partner Stedman Graham these days, which is exactly why this weekend’s outing in Chicago is getting so much attention.
Winfrey, 72, and Graham, 75, stepped out together at a 15-year reunion for the crew of “The Oprah Winfrey Show,” held at Chef Art Smith’s restaurant Reunion on Navy Pier.
It marked their first joint public appearance since the Tyler Perry Studios grand opening gala back in 2019, and it came just weeks ahead of a milestone that made the whole gathering feel extra meaningful.
September 8 will mark 40 years since “The Oprah Winfrey Show” first premiered, and Winfrey clearly wanted to celebrate the anniversary with the people who helped build it alongside her.
The reunion was organized by Ty Owens, described in Winfrey’s own account of the day as the person who “managed to keep the Harpo garage straight as parking manager,” and who took it upon himself to bring former Harpo Studios staffers back together in one room.
Winfrey shared a lengthy caption on social media explaining how she ended up there, writing, “I can’t believe that this September 8 marks 40 years since The Oprah Show debuted! And I heard that Ty Owens… was bringing everyone who worked at Harpo together to celebrate, so I made my way to Chicago to join in on the memories.”
She continued thanking the people who made the night happen, writing, “Thank you, Ty, for your spirit of community and for bringing us all together. My gratitude to Chef Art Smith for having us at his restaurant, aptly called Reunion. To my Harpo crew, for being the greatest team ever!”
She closed her message on an especially warm note, extending her gratitude to everyone who worked behind the scenes over the decades and hinting that even more celebrating is coming.
“And to ‘all my children’ who got raised from The Oprah Show by me, your mamas, and grandmamas, we’ll celebrate on the Oprah Podcast in September,” she wrote, pointing fans toward a bigger anniversary tribute still to come.
A Rare Sighting of Oprah and Stedman, Fried Chicken Included
The reunion itself looked like exactly the kind of joyful, low-key gathering longtime staffers would want after not seeing each other in years.
Photos and videos from the night showed Winfrey and Graham posing alongside Chef Art Smith, with one shot capturing all three of them holding up a massive platter of fried chicken.
In one video shared to the restaurant’s own Instagram account, Winfrey can be heard cheerfully announcing the food of the evening, saying simply, “Hey, Art’s fried chicken!” At the same time, Smith and Graham held up the towering plate for the camera.
The gathering was captured and shared publicly by Jill Van Lokeren, a former senior supervising producer on “The Oprah Winfrey Show,” who posted a carousel of photos from the celebration.
In her caption, she called it a night of pure joy among old colleagues, writing, “15 year reunion for The Oprah Winfrey Show. The best segment, a surprise guest showed up. A night of all love and pure joy. Forever grateful, Oprah.”
She also thanked the host of the evening directly, adding, “Plus Chef Art Smith hosting at his fabulous Reunion was an added treat! Love our Ty for organizing.”
Smith echoed that sentiment on his own restaurant’s Instagram account, writing that his team was “filled with gratitude” to host Winfrey and the old Harpo crew, and calling Winfrey “a true Chicago legend” who has “touched countless lives throughout the years.”
For the occasion, Winfrey kept her look casual and comfortable, wearing a cream-colored pinstriped blazer and matching trousers with white sneakers and sunglasses, a far cry from the glamorous gowns she is more often photographed in.
Graham, meanwhile, looked considerably more formal in a black suit paired with a crisp white button-down shirt, sticking to the dapper, buttoned-up style he has long favored on the rare occasions he does appear in public alongside Winfrey.
Both of them appeared relaxed and clearly enjoying the company of people who had spent years working alongside them during the show’s original run.
Forty Years Together, No Wedding, and No Regrets
Winfrey and Graham’s relationship stretches back to the show they were both celebrating. The two met at a charity event in 1986, the very same year “The Oprah Winfrey Show” debuted, and they have remained together ever since without ever walking down the aisle.
Graham proposed in 1992, and Winfrey said yes, but the couple ultimately called off the engagement the following year. Winfrey explained her change of heart candidly in a 2020 essay for O magazine, revealing that doubts crept in almost immediately after she accepted the proposal.
“I realized I didn’t actually want a marriage. I wanted to be asked,” she wrote. “I wanted to know he felt I was worthy of being his missus, but I didn’t want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work.”
She went on to explain that both she and Graham have long agreed that marriage would not have suited the life they built together, largely because her career became so consuming. “My life with the show was my priority, and we both knew it,” she wrote. “He and I agree that had we tied the marital knot, we would not still be together.”
It is a rare level of honesty about a decades-long relationship from two people who have otherwise gone out of their way to keep the details of their romance private, choosing to let their actions, rather than public statements, define the partnership.
That same instinct toward privacy appears to be part of why sightings of the couple together are so infrequent.
Winfrey has previously explained that keeping a lower profile with Graham became a deliberate choice once she realized how much media attention followed even a single new photo of the two of them.
Every fresh appearance seemed to generate a fresh wave of speculation about their relationship, so scaling back joint public outings became one way to keep that speculation at bay.
Against that backdrop, showing up together for something as meaningful as the 40th anniversary of the show that essentially launched alongside their relationship makes this particular reunion feel less like a random sighting and more like a deliberate, sentimental choice.
Winfrey has also been open over the years about her decision not to have children, a topic that tends to come up whenever her long, unmarried partnership with Graham is discussed.
She has said she never felt a strong pull toward traditional motherhood, telling People magazine in the past that she understood the depth of “responsibility and sacrifice” the role requires and knew early on it was not the path for her.
Instead, she has poured that maternal instinct into the Oprah Winfrey Leadership Academy for Girls in South Africa, a school she founded in 2007 for academically gifted girls from disadvantaged backgrounds.
She has referred to the academy’s students as the daughters she never had, once telling People, “They are my greatest, deepest joy,” and describing the role the school has played in her life as a fulfilling stand-in for a version of motherhood she never sought out for herself.
Taken together, the reunion, the anniversary, and the rare sighting of Winfrey and Graham side by side tell a fuller story than a single photo op ever could.
Forty years after they first crossed paths at that charity event, and forty years after “The Oprah Winfrey Show” first went on the air, both of those chapters of Winfrey’s life are still standing, still connected, and apparently still worth celebrating with the people who lived through it all alongside her.
Fans hoping for more will not have to wait long, since Winfrey has already teased that a fuller anniversary celebration is coming to her podcast in September, timed to the actual 40-year mark of the show that started it all.
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