Who is Oprah Winfrey dating? Who Oprah Winfrey dated; list of Oprah Winfrey loves, ex boyfriends; breakup rumors. The loves and relationships of Oprah Winfrey, listed by most recent. While it's maybe a little scandalous that gal pal Gayle King isn't on the list, more shocking still would be if she were added to the list amidst the discovery of an Oprah starring celeb sex tape. Not that the multi-media mogul would ever allow a celebrity sex tape to surface (if it were ever to exist), but what a trip to think of Oprah co-mingling with the likes of Tommy Lee on the list of celebrities with sex tapes .