While speaking with Hip Hop Motivation, Roc-A-Fella Records co-founder Dame Dash offered some insight into his past relationship with Aaliyah. He later revealed that Jay Z, who knew Aaliyah before he did, tried to also get with the singer. Dame went on to explain that she was usually willing to give someone a shot, but was also quick to place them in the “friend zone.”
“So, I was going at her,” he said. “But Jay was going at her. And he knew her before I did…It was just a situation where Aaliyah was the type of girl that would give you a shot. 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. She just wasn’t—Or at least that was my experience…We just hung out. That was my dude.”
Dame Dash was Aaliyah's man (and Jay-Z's best friend) before she died.
Aaliyah was also 21, and Jay-Z was 30 before she started dating Dame Dash.
This is why I feel like that relationship wouldn't have lasted much longer has she stayed alive, his arrogance would seem like a huge turn off and unbearable after awhile.