In 1967, Vietnam War protests raged nationwide, the 25th Amendment was added to the United States Constitution and a young Oprah Winfrey found The One. "I was a 13-year-old girl living in Milwaukee, and I thought I'd found my prince," she says.
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.
In October 2010, Oprah was having a run-of-the-mill meeting with her producers when the man of her teenage dreams walked through the door. "Why don't you change clothes and we'll go across the street and get something to eat?" Jackie asks.
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!"
Once Oprah is ready, Jackie picks her up outside her office and walks her across the street to a French bistro. "Our date lasted almost two hours," Oprah says. "But Jackie's so charming, the time just flew by."
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.
Now a father with two grown children, Jackie says his Jackson 5 days feel surreal. "It feels like a dream come true," he says. "We were destined to be entertainers and stars, and we didn't know it was going to be that big."
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 fame and fortune was a far cry from the two-bedroom house his 12-person family shared in Gary, Indiana. "When I was there, I thought it was a big mansion," he says. "Then I went back and I go: 'I can't believe I lived in this house. My garage is bigger than that house.'"
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."
At the end of the evening, Oprah thanks Jackie for her full-circle moment. "To be a kid on welfare watching you guys come out on TV for the first time, ... I was really just a teenage girl, 13, 14, 15, 16, never even imagining that it could really come true," she says. "And then to be able to have this moment with you..."
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."