February 21, 2015 - Jason Merritt/Getty Images North America more pics like this »
Oprah Winfrey And Stedman Graham
Length of Engagement:  25 years

Winfrey and Graham were originally engaged back in 1993, and have been enjoying a long engagement ever since. But for them, an engagement is better than marriage.

Winfrey shared with Vogue, “The only time I brought it up was when I said to Stedman, ‘What would have happened if we had actually gotten married?’ And the answer is: ‘We wouldn’t be together.’ We would not have stayed together, because marriage requires a different way of being in this world. His interpretation of what it means to be a husband and what it would mean for me to be a wife would have been pretty traditional, and I would not have been able to fit into that.”