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.
Roger Ebert and Oprah WinfreyBack 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."
St. Louis County
iStock / evgenyb
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