Oprah Winfrey and Stedman Graham made a rare public appearance together in Chicago at USA Today. The couple attended an event celebrating the upcoming 40th anniversary of The Oprah Winfrey Show, joining friends, family, and former Harpo Studios crew members. TV producer Jill Van Lokeren shared a photo on USA Today showing Winfrey and Graham posing alongside former private chef Art Smith with a large platter of fried chicken from his restaurant Reunion.
Rare Joint Appearance in Chicago
For the occasion, the 72-year-old media mogul wore a cream pinstriped blazer and matching pants with white shoes and tinted sunglasses. Her 75-year-old partner, the CEO of S. Graham & Associates, wore a classic black suit over a white button-down shirt with dress shoes. The outing marked the pair’s first public appearance together since they attended the Tyler Perry Studios grand opening gala in Atlanta in October 2019.
Decades-Long Romance and Keeping a Low Profile
Winfrey and Graham have been together since 1986, the same year her daytime talk show began. Over the decades, the couple has largely kept their relationship out of the public eye. Winfrey has previously explained that they stepped back from making frequent public appearances together because of constant tabloid speculation. According to HELLO! Magazine, she once sought advice from poet Maya Angelou regarding the media noise, recalling that Angelou advised her that people writing stories were simply trying to sell publications. Winfrey noted that she realized every new photograph together generated a new story.
Why the Couple Chose Not to Marry
The couple became engaged in 1992, but ultimately decided against getting married. In a 2020 essay published in O, The Oprah Magazine, Winfrey detailed her thoughts on their arrangement. In 1993, the moment after I said yes to his proposal, I had doubts. I realized I didn’t actually want a marriage. I wanted to be asked,
she wrote. She added that while she wanted to know he felt she was worthy of being his wife, she did not want the day-in-day-out compromises required for a marriage, noting that her priority at the time was her television show. Winfrey stated that they both agreed they would not still be together had they tied the knot, describing their bond instead as a spiritual partnership
that allowed Graham to maintain an independent identity and purpose.
Establishing Independent Careers
Graham has built an independent career as a businessman, best-selling author, motivational speaker, and the head of his own marketing and management firm. Addressing their dynamic in past interviews, Graham emphasized his support for Winfrey’s success and his satisfaction with his own path. The thing about our relationship is, so I’m dedicated to her happiness, so that’s great for her,
Graham said during an appearance on The Ellen DeGeneres Show. And I want her to be the best she can possibly be, and she’s done a pretty good job of doing that. And so for me, I’ve been able to find my own happiness, my own skills, my own talents, my own abilities, and I’m satisfied with that.
