We all love our celebrities, especially when they pair up. But sometimes their tastes when it comes to matters of the heart can leave us scratching our heads.
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Reuters
Roger Ebert and Oprah Winfrey Back when the movie reviewer and the soon-to-be "Queen of All Media" were both starting out in Chicago, Ebert and Winfrey co-hosted the Chicago Emmy Awards in 1986 and went on two dates. In 2005, Ebert even jokingly took credit for some of Oprah's success, writing "Yes, it is true, I persuaded Oprah to become the most successful and famous woman in the world."