Before Beyonce, Jay-Z Was Apparently Very Interested in Dating Aaliyah

It's hard to imagine the man who is married to Beyoncé being interested in any other woman, but there was a time before Jay-Z was married to Queen B. Apparently, Jay-Z was once quite interested in starting a relationship with pop star Aaliyah, who died in a plane crash when she was just 22 years old at the height of her career.

Following the news that Jay-Z was interested in a relationship with Aaliyah, many wanted to know whether the two ever actually dated. Here's what we know.

Damon Dash, who himself had his own relationship with the young pop star, explained that no one was pursuing Aaliyah as aggressively as Jay-Z was.

"I did not know Jay was trying to holler at her, but then it just happened like that. He was trying, I was trying. Everybody was trying — he was going hard," Damon said during a 2009 interview with Page Six. Although that was Damon's version of events, there are apparently some other perspectives on what happened.

"Dame went behind [Jay-Z’s] back and hollered at [Aaliyah]," producer Choke No Joke claimed.

So it's unclear whether Aaliyah and Jay-Z ever sort of dated, but Damon said that Aaliyah was willing to consider a relationship with basically anyone.

"It was just a situation where Aaliyah was the type of girl that would give you a shot," he said. "She didn’t care what people thought or whatever. So, she’ll date you and be your friend."

"You might end up in the friend zone. A lot of times, that’s what happened. You weren’t just going to hit that," he added. That appears to be exactly what happened to Jay-Z, who was, notably, nine years older than Aaliyah at the time when he was trying to court her.

While Damon has been talking about Jay-Z and Aaliyah's potential affair, Jay-Z and Damon, who used to be business partners, aren't talking much at all.

After collaborating with each other through the early part of Jay-Z's career, they ended their collaboration in 2003. While Damon maintained that the two were still friends, he did sue Jay-Z in 2021 over the streaming rights to his 1996 album "Reasonable Doubts."

In 2023, Damon said that he thought there was still a chance that the two of them could reconcile with one another.

"I always said as a man that we could always talk it up," Damon said. "Men should always be able to talk things up, but I’m really happy with my life right now. I know the world would love to see it and I’m down for it."

Jay-Z has not commented on the end of their relationship.

Of course, there are plenty of "what ifs" related to Aaliyah precisely because her life was so short. Relationships were far from the only thing she was dealing with, and it's difficult to say where her life would have gone as she continued to grow and age.