Rumors about a romantic relationship between Jay-Z and Aaliyah have circulated since the late ’90s, fueled by their public appearances together and speculation about their personal lives. However, Aaliyah never publicly confirmed any romantic involvement with Jay-Z. Despite this, Jay-Z’s former business partner, Damon Dash, has claimed that the rapper was deeply infatuated with Aaliyah and pursued her romantically. Here’s what Choke No Joke recently said about Jay-Z wanting to keep his relationship with Aaliyah private.

Damon Dash spoke in 2019 about Jay-Z and Aaliyah’s alleged relationship

Jay-Z and Damon Dash share a complex history that began in the early ’90s when they co-founded Roc-A-Fella Records, a label that would become a powerhouse in hip-hop. Dash, known for his brash, entrepreneurial energy, handled much of the business side, while Jay-Z focused on his artistry. Their dynamic partnership fueled both their successes. Over time, however, tensions emerged as disputes over ownership, creative control, and financial decisions grew, leading to a very public split.

In 2019, Dash spoke to Page Six about Jay-Z and Aaliyah. According to Dash, Jay-Z pursued the “Try Again” singer. Dash and Aaliyah famously dated in 2000 before she died in a plane crash in 2001.

“He tried very hard,” Dash said of Jay-Z.

“I did not mean to fall in love with Aaliyah; she was just that cool,” he continued. “But you know, we were both going hard … everybody was trying to get to Aaliyah — it was not just Jay.”

Dash went on to call Aaliyah “cool as hell” and talked about falling in love with her personality. “There was never any obligation or any title … just liking being around somebody for who they are,” he continued. “I was not in love with Aaliyah through the television. I fell in love with her from hanging out and meeting her. She looked different than Aaliyah on the TV screen.”

As for Jay-Z, he claimed he “did not know Jay was trying to holler at her.”

Choke No Joke talked about Jay-Z and Aaliyah on a podcast in September 2025

Arthur D. Alston III, known professionally as Choke No Joke, is a multifaceted figure in the entertainment industry with over 30 years of experience. Choke was the former videographer for Roc-A-Fella Records, which is how he knew Damon Dash and Jay-Z. In September 2025, he spoke on The Willie D Live Podcast about how Aaliyah was “Jay-Z’s girl” before she dated Dash.

“I could show you pictures of Jay-Z and Aaliyah when they were together,” Choke alleged. “Case in point, 2000, Lil’ Kim had an album release party at the Puck Building. Jay-Z and Aaliyah came in together … as a couple. … I went over to them to interview them. Jay said, ‘Yo, yeah, you can do it, but do it separate.’ You know what I’m saying? Because he didn’t want the world to know Aaliyah was his chick.”

“Jay’s always been private like that,” Choke continued. “Even when he was dating Beyoncé, it was a secret, you know what I’m saying?”

Choke No Joke alleged why the Roc-A-Fella partners truly had a falling out

In October 2024, Choke No Joke told HYPE+ that Damon Dash and Jay-Z’s real falling out had to do with Aaliyah.

“That’s more than 50% of it,” Choke said regarding why the Roc-A-Fella partners stopped doing business together.

“Jay was with her first,” Choke alleged.

This goes against what Damon Dash said about his falling out with Jay-Z. Dash previously commented about how he wasn’t receiving royalties from Roc-A-Fella Records. He also claimed that Jay-Z’s working with R. Kelly was particularly difficult for him. With this in mind, it seems likely that the end of Roc-A-Fella was multifaceted and more complicated than just what went down between Jay-Z, Dash, and Aaliyah.

For more news and exclusive interviews, follow Showbiz Cheat Sheet’s Instagram.