If you watched the Janet Jackson documentary on Lifetime this past weekend, there was plenty to learn about the pop culture icon (you can check out a recap of the biggest moments from night one and night two here on ESSENCE.com). One of the most talked about parts was the insight given into Jackson’s long-term relationship with producer Jermaine Dupri. While they were attached at the hip throughout the aughts (’02 to ’09), fans had no idea how deep their relationship really was and how much Jackson loved him.

“I really thought that was going to be it for me,” Jackson said as video ran of the two during their relationship. The clips showed the starlet hanging out in his native Atlanta, opening up about her desire to have children with him (as many children as he desired at that).

But the fairytale ending she was hoping for, and one would assume he wanted since he asked her to marry him at one point, failed to come to fruition due to a number of things. The most glaring reason for fans was Dupri’s penchant for stepping out on their relationship, or as he put it, “Me being reckless.”

“One of the weird things about dating Janet is that dating Janet attracts other women,” he said. “Girls wanted to talk to me more because I was dating her, which was really weird. And…I was a man [laughs].”

But as Jackson would share, the hurt of those choices wasn’t the sole reason they couldn’t work.

“I needed more than what he was giving me,” she said. “He was a workaholic. He was constantly working. I would not see him for three weeks, a month.”

She added, “As soon as he could come in, he would go to the club. It was like, ‘carve out just a little bit of time for me. Even if it’s just us hanging at home,’ and it was hard for him to do. I would always tell him I never thought he had enough time really for a girlfriend. His girlfriend was his work.”

Being non-confrontational, Dupri didn’t fight — not even for the relationship. It’s not something he necessarily regretted but just acknowledged as a fact in the doc.

“I’m sure I could have fought much harder and it would have been something that would have never gone away,” he said.

The relationship ended in 2009, and a year later she started dating Qatari businessman Wissam Al Mana. They would go on to marry in 2012 and welcome a son in 2017 — months before they announced they were going their separate ways.

As both are seemingly available, would we want to see them reunite? Probably not. Still, we can always look back at the sweet moments they had when they were in love years ago and remember the time — as Jackson’s older brother used to say. Check out the Janet and Jermaine years in photos below.

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