"He was my first love and very much so," she said. "And there was a lot going on in our relationship, a lot going on with him, I should say. And -- just being so young and not really -- not really knowing what life is really all about, just beginning to explore life and wanting to -- help him, thinking I could change him, if I only could do this and that, and not realizing that it was something that he had to do and want for himself."
Their marriage was annulled and she did not find love again until she met Rene Elizondo Jr., a songwriter and one of her musical collaborators. The two were secretly married for eight years, but it ended with a painful divorce.
Music producer and record company executive Jermaine Dupri was the latest man in Jackson's life. The couple dated on and off for seven years, producing two of her chart-topping albums together, but parted ways. Their relationship made headlines this summer when rumors of a possible marriage circulated.
For the pop star who has gone to great lengths to keep her private life hidden, Jackson addressed the rumors, telling Roberts that she was not married to Dupri.
"No, I'm not," she said. "I know people thought we were. … I just heard that today. Someone said to me, or just yesterday, someone said, 'You engaged,' and I said, 'Who am I engaged to?' And they said to Jermaine. I said, 'Oh, I am?'"
In fact, she confirmed that they are no longer together.
"I adore him. Absolutely adore Jermaine," she said. "Love him to death and we're still very good friends to this day. Very good friends, but that's all I'll say."
Jackson said she is single and focusing on her work -- a new music video for her single, "Make Me," and a book entitled "True You," a personal story about her lifelong struggle to control her weight.
Between 100 million records sold, five Grammys and legions of fans around the world, it's hard to believe that Jackson has spent a lifetime in search of her true self.
"Just picking yourself apart all the time because you're so used to being kind of picked apart," she said. "'Oh, your butt's too big,' and 'you've got too much meat here,' 'got too much this there.' ...Well, now I know there's nothing wrong with [my booty], thank you to Jermaine Dupri."
Five months since Michael's death, Jackson said she has found refuge in her work.
"I needed to get back to work. It helped me get through it," she said. "I was able to put a lot of my focus someplace else."
With the release of the documentary "This Is It," which shows Michael preparing for his sold-out summer concert tour, she has been bombarded by painful images of Michael.
"I haven't seen [the film]. I definitely won't, not right now. I don't know if I will ever see it," she said. "...It's hard when I see a poster, you know, the "This Is It" posters that are around the city. That's tough. I've seen the commercial. They advertise -- the trailers -- on TV. That was tough."
If her brother were here, she told Roberts he would tell her to "stop and enjoy" life.
"I think it would be to stop and enjoy. I think that would be it," she said.
It's advice she may well heed during this time of shifting priorities and self-reflection.
"I'm in a different space. There's a lot that's gone on, a lot that makes you think, think about life. Something that I think we tend to -- at times take for granted," she said. "I'd love to have a family."