According to a Gawker exclusive written by famed biographer Kitty Kelly, Oprah Winfrey had an intimate relationship with a man named Reginald Chevalier.
Shortly after Oprah: A Biography hit shelves, Kelly was contacted by Chevalier, and apparently his story checks out.
How did the relationship begin? Oprah plucked him off the stage of her show, of course. From Kelly's post:
"Chevalier said he met Oprah when he appeared on her show in 1985. 'She
was doing a segment on look-alikes and at the time I looked like Billy
Dee Williams. She later confided that she instructed her producers to
keep me backstage after the show. She threatened to fire them, if I got
away. She took me to lunch at the Water Tower restaurant and ordered
stuffed mashed potatoes for both of us.' Their affair began that day."