Oprah Winfrey and Stedman Graham

In 1986, Oprah Winfrey’s eponymous show hit the airwaves, bringing her fame and fortune. That same year, she began dating Stedman Graham, a former athlete and sportswear model. Interestingly, it was not love at first sight for her. Graham was seeing someone else then, and she didn’t think much of their encounter.

However, fate had other plans. They later reconnected when they visited an ill mutual friend, and sparks flew. After getting engaged in 1992, they called off their wedding the following year. In hindsight, they both believe that getting married would have put too much pressure on their relationship, ultimately leading to its demise.