Oprah Winfrey & Stedman Graham – 37 Years

Stedman Graham and TV host Oprah have a lot to be proud of, but primarily their lasting relationship. The couple had met the same year “The Oprah Winfrey Show” first aired in 1986. Interestingly, she was initially wary of him, finding his 6’6″ frame a bit too attractive and believing he was a “player.”

The famously private couple announced their engagement in 1992, with plans to wed the following year. However, the wedding never took place, but even so, they have been a strong force to reckon with. Perhaps, their date nights, where Oprah cooks meals for Graham, made their enduring relationship last.