Jay-Z Lost a Competition for Aaliyah’s Romantic Attention

Aaliyah had two men competing for her attention. Jay-Z, who was interested in her, reportedly wasn't thrilled about this.

At the end of Aaliyah’s life, she was romantically involved with Damon Dash. The couple had a relatively brief but reportedly intense relationship; Dash said that within six months they began discussing the possibility of marriage. When he was first pursuing her, though, he was in competition with Jay-Z. Dash said that both he and Jay-Z were working to impress Aaliyah at the same time.

Damon Dash said he and Jay-Z were both pursuing Aaliyah at the same time

According to Dash, he hadn’t thought much of Aaliyah when they first met. When he began to develop feelings for her, he tried his best to impress her. Unfortunately, he realized he was not the only one in pursuit of her affection. Jay-Z was also interested in Aaliyah.

“I just threw my A-game,” he said on the That’s F***ed Up podcast (via Vibe Magazine). “And then, you know, I guess Jay was trying to get at her as well, and I didn’t know. It got brought up and I was like, ‘F*** both of y’all.’ But it never worked out for them, and we were both trying to get at her. And I kind of eased up, but then we ran into each other. It’s a long story.”

Dash said that Jay-Z wasn’t happy to be competing with him. This didn’t stop him, though.

“Yeah, he felt a way [about me pursuing her]. But everybody knows that s***,” Dash said. “They be trying to act like he was really f***ing with her. Nah, he was sending flowers and doing all that s***, he was courting her. So we were both going hard and we ended up in the same house for 4th of July.”

For a while, Dash said Aaliyah seemed equally interested in both of them. During the 4th of July trip, though, he won her over.

“It was, like, one day [Aaliyah] might lean towards him then it’ll lean towards me,” he said. “But I was just on fire that week. Everything I was saying was funny, you know what I’m saying?”

Aaliyah denied dating both Jay-Z and Damon Dash

While Aaliyah and Dash were together in the time before her 2001 death, she denied their romantic connection. She liked to keep her private life fully private, and simply referred to him as a close friend in interviews.

“I think rumors are hilarious,” she told Vibe Magazine in 2001. “I don’t pay any attention. It goes in one ear and out the other. When you’re in the business, you hang out with people, and people are like, ‘I wonder, are they seeing each other?’ I never dated Jay. I never dated Ginuwine. Damon and I are very good friends. I’ll keep it at that right now.”

Damon Dash spoke about their relationship after her death

Dash said he greatly valued the time he had with Aaliyah. In the years since her death, he said he has thought of her every day.

“I was reflecting [that] there hasn’t been one day since she’s passed, not one in the 20 years, that I haven’t either heard her name, heard her record, or seen a picture of her,” he told Entertainment Tonight. “Every single day she’s present in my life and I feel lucky for that.”

When he hears her songs, he feels that she is directly reaching out to him from beyond the grave.

“They’re signs to me, it means she’s talking to me,” he said. “You know, because sometimes things will come on and people will say her name in other songs when I’m bringing her up, or [say] that she’s a living angel — now she’s an angel for real. So, you know, she looks out for the people that she loves, that’s how I feel.”