Oprah Winfrey, Stedman Graham
Beyond the legal drinking age! The queen of media got engaged to her longtime beau in October 1992, but told Access Hollywood in September 2013 that she’s not the marrying type. “If you ever interviewed him, he would tell you that had we married, we would not be together today,” she said, adding that the “wife” title comes with expectations. “He’s a traditional man, and this is a very untraditional relationship,” Winfrey quipped.
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