Jackie asks Oprah to dinner, and she nervously gets ready. "When Jackie says, 'Let's go across the street and get a bite', the first thing I said, 'Oh no, that's okay,'" she says. "Because I'm thinking, 'When's the last time I had to be a fun date?' A long time. Ask Stedman, he'll tell you."

Watch Oprah prepare for her date with Jackie Jackson

When Oprah's ready, Jackie picks her up outside her office and escorts her to dinner. "It was interesting because I was thinking, 'What would happen if I had married Jackie Jackson?'" she says. "I would have been Michael Jackson's sister-in-law. Little Janet would be coming to my house, we'd be cooking together. Who knows?"