Oprah's Dream Date
Oprah's first love was none other than Jackie Jackson of the Jackson 5. "Everybody was going nuts over little Michael, but being a little older, it was his big brother, Jackie, who made my heart go pitter, pitter, pitter-patter," she says. "That was my goal—to marry Jackie Jackson."
Sadly, their love was not meant to be. Jackie married in 1974. "I was crushed," Oprah says. "Hey, a girl could dream."
Still, young Oprah never could have imagined her dream date would come knocking 43 years later.
Oprah is floored. "Thank God Stedman's in Bermuda," Oprah jokes. "I can't believe I have no lipstick on when Jackie Jackson is here!"
Watch Jackie surprise Oprah
At their table for two, Oprah finally gets to pose the questions her teenage self dreamed of asking—including what it was like to perform on The Ed Sullivan Show for the first time. "At that time, it was just like a bunch of guys that had a dream," he says. "Our dream was to be professional singers and to be the best we could be."
Jackie says he didn't realize the impact of that appearance until he went back to school for the first time. "Kids were coming in from other schools in the hallways screaming," he says.
Oprah: "What were those years like for you? Because I was one of those screaming teenagers. ... Like, 'Oh, my God, Jackie Jackson!' When you would come onstage I would always find you first."
Jackie: "Oh, really?"
Oprah: "Yes. Didn't you have lots of fan letters from girls who were sending you their love letters?"
Jackie: "Yes, but I thought all the fans were in love with Jermaine and Michael. I thought they didn't pay any attention to me. I was the oldest."
Oprah: "I was. ... I think I wrote you letters, I just didn't know where to send them."
Jackie: "Oh, you did?"
Oprah: "Yes. And I'd wake up thinking about you and wondering what city you were in."
Jackie says the family wouldn't be where they are now without his father, Joe. "I'm proud that my father did raise us the right way. But when I was growing up, I thought he was kind of hard at the time," he says. "It was a tough neighborhood. He had to be stern. I can look back on it and say he did such a wonderful job."
Growing up, Jackie says he also felt extra responsibility as the oldest boy to make sure his brothers were safe. "I was so protective over my brothers," he says.
Still, Jackie says he was the most reserved. "I was always quiet," he says. "Michael was a quiet person too."
Jackie says Michael was also the biggest prankster—and the most balanced when it came to handling fame. "When he hit the stage, he was a different person," he says. "I knew that from the very beginning that he had the magic."
Ever the gentleman, Jackie walked Oprah back to her office and ended the night with a small kiss. "So I went home [that] night and I wrote in my diary: 'Jackie Jackson. It finally happened,'" she says. "That was so surreal for me. It says that dreams still can come true."
Listen to what Oprah told Gayle about the date the morning after
50 years of boy bands
Look back at the Tiger Beat covers of your youth
Shaun Cassidy, all grown up
The Backstreet Boys reunite
Peter Frampton rocks on