The Truth About Jay-Z And Aaliyahs Relationship

Highlights

• Aaliyah always kept her romances private, including her relationship with Dame Dash from 2000, until her tragic plane crash in 2001.
• Jay-Z allegedly pursued Aaliyah "hard" in 1999, but Dame Dash ultimately won her over, leading Jay-Z to remain in the friend zone.
• A rift between Jay-Z and Dash ended their collaboration in 2003, with ongoing legal battles over streaming rights and copyright ownership.

In 2001, the music industry lost Aaliyah, a talented and promising young icon. She was devastatingly killed in a plane crash at the age of 22. The "Try Again" hitmaker was at the height of her career — every girl wanted to be her and all the boys wanted her. But despite being linked to several men at that time, the R&B singer always kept her love life private. At least, except for her now-publicized illegal marriage to R. Kelly when she was only 15-years-old.

But in 2021, Damon Dash spilled some secrets about the At Your Best singer's romantic life. Aaliyah never spoke about their relationship in public, but the record executive later revealed that they dated from 2000 until her death. They had even discussed marriage. But Dash's biggest revelation was about the fling between Aaliyah and Jay-Z. The rapper apparently tried "very hard" to get her.

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An Inside Look At Aaliyah And Jay-Z's Relationship

Aaliyah and Jay-Z dated briefly in 1999

In an interview with Page Six in 2009, Dash said that "everybody was trying to get to Aaliyah." However, he said he never pursued her as "hard" as Jay-Z did. The "99 Problems" rapper was rumored to be dating the Queen of the Damned actress in 1999. They were 29 and 20, respectively.

But soon, Dash won Aaliyah over and her fling with Jay-Z never materialized. "I did not know Jay was trying to holler at her, but then it just happened like that," the film producer said about unexpectedly falling for the "One in a Million" singer. "He was trying, I was trying. Everybody was trying — he was going hard."

Then there was this different version of the story: "Dame went behind [Jay-Z’s] back and hollered at [Aaliyah]." It came from producer Choke No Joke, who worked at Roc-A-Fella Records — a hip-hop label co-founded by Dash, Jay-Z, and Kareem "Biggs" Burke.

Contrary to what was implied in Choke No Joke's statement, it appears that the former Roc-A-Fella owners drifted apart due to professional conflicts. Aaliyah even hung out at the house Dash and Jay-Z shared weeks before the tragic accident.

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Aaliyah Might Have Actually Dumped Jay-Z

Aaliyah started dating Dame Dash and that may have been what caused her to stop seeing Jay-Z

According to Dash, Aaliyah and Jay-Z were not seriously dating. "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," the entertainment executive said.

He continued: "You might end up in the friend zone. A lot of times, that’s what happened. You weren’t just going to hit that."

By the looks of it, that's exactly where the "Big Pimpin" rapper landed. During the Princess of R&B's funeral, Jay-Z paid his respects as a friend. As a tribute, he released a remix of her single, "I Miss You."

Inside Jay-Z And Dame Dash's Rift

Jay-Z and Dame Dash had a falling out over an album being produced by Rock-A-Fella Records

In 2003, Jay-Z and Dash put an end to their collaboration due to creative differences. "We’ve always been polar opposites," the rapper said. For a while, they maintained that they were still friends.

Fast-forward to 2021: Dash went forward in suing Jay-Z over the streaming rights for his 1996 studio album, Reasonable Doubt.

Prior to that, Roc-A-Fella filed a lawsuit against Dash, who allegedly tried to sell the album's copyright as a non-fungible token (NFT).

In 2023, Dash said that he was willing to put the beef had with Jay-Z behind him.

"I always said as a man that we could always talk it up," Dash explained. "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 status of the relationship with Dash, three decades after their falling out.

Source: Page Six

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