Oprah Winfrey and Stedman Graham – 33 Years

Media mogul and businesswoman, Oprah Winfrey, has always had the emotional support from her man, Stedman Graham. However, despite the fact that they started dating in 1986 and announced their engagement in 1992, this couple never married. According to Oprah, it’s what works best for her and Stedman.

Stedman, who is a successful businessman in his own right, says he’s happy to support Oprah in whatever project she embarks on, even hinting that he thinks she would be great at politics. In 2018, Oprah starred in the film adaptation of A Wrinkle In Time.