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Oprah Winfrey and Stedman Graham Appear Together at Chicago Reunion

The rare sighting drew renewed attention to their private, four-decade partnership as celebrations mark The Oprah Winfrey Show’s 40th anniversary.

Overview

  • The couple made a rare joint outing in Chicago over the weekend, joining a reunion of former Oprah Winfrey Show staff at Chef Art Smith’s Reunion restaurant on Navy Pier.
  • Images and video of Winfrey and Stedman Graham posing with chef Art Smith and a platter of fried chicken were posted to Instagram by former producer Jill Van Lokeren and widely circulated by news outlets.
  • This was their first major public appearance together since 2019, when they attended the Tyler Perry Studios grand opening gala, which underscored how seldom they now step out as a pair.
  • Oprah has publicly described their relationship as a ‘spiritual partnership’ and has written that she accepted a 1992 proposal before deciding traditional marriage was not right for her, while Graham maintains his own career as founder and CEO of S. Graham & Associates.
  • The reunion both celebrates Winfrey’s professional legacy ahead of the Sept. 8, 2026, 40th-anniversary milestone and reminds the public that the couple controls their exposure to avoid recurring tabloid narratives.