Oprah Winfrey & Stedman Graham

Oprah Winfrey is known as the queen of media for a reason. Every show she has ever been on or created has been a hit. As such, she has built a net worth of $3.5 billion. Despite this, she has never married, although she has been in relationships. Many of them were abusive, though.

But one relationship flourished, and that is with Stedman Graham. They started dating in 1986 and got engaged in 1992, but they have never looked like they want to get married. They are happily engaged, though, and at least Stedman has a $10 million fortune, so no one can say he’s sticking around for the money.