Jay-Z's dating history before Beyoncé revealed in relationship timeline from 1999-2002

Jay-Z was a serial dater who had not yet settled down with megastar Beyoncé at the time he is accused of raping a 13-year-old girl with his friend Diddy. 

The 55-year-old rapper, whose real name is Shawn Carter, vehemently denies allegations he raped a young girl with Diddy at an afterparty following the MTV Video Music Awards in September 2000. 

Beyoncé, 43, who married Jay-Z in 2008, is standing by him and has not publicly addressed the claims. 

The lawsuit was initially filed in New York's Southern District this past October against Combs but the alleged victim filed an amended complaint on December 8 and named the '99 Problems' rapper, 55, whose real name is Shawn Carter. 

Jay-Z has closely guarded his relationship history prior to Beyoncé. He was romantically linked to various women in 2000, including actress Rosario Dawson, R&B singer Blu Cantrell, rapper Charli Baltimore and video vixen Karrin Steffans.

He was also spotted with the late singer Aaliyah, who had been victimized by R. Kelly as a minor, and died in a plane crash in 2001. 

The Jay-Z rape accuser claims that a female celebrity watched as he and Combs allegedly raped her. The female star has not yet been named.

Jay-Z attended the VMA's without a date, whereas Diddy walked the red carpet with his then girlfriend, Jennifer Lopez. 

She is not named in the lawsuit and there is no suggestion she was involved in anyway in the alleged attack.

Jay-Z was also rumored to have been courting R&B star Aaliyah, who ended up dating the rapper's Roc-A-Fella business partner, Damon 'Dame' Dash, until she died from a plane crash in 2001.

'I guess Jay was also trying to get at her as well, and I didn't know,' Dash said in an interview last year.  

'It never worked out for them but we were both tryin to get at her. Everyone was getting at Aaliyah.'

Dash claimed Jay-Z was 'obviously' bitter that Aaliyah did not welcome his advances. 

'Yeah, he felt a way,' Dash said of Jay-Z. 'He was sending her flowers. He was courting her.'

There is some uncertainty over exactly when Beyoncé and Jay-Z started dating. He told Vanity Fair they were 'just beginning to try to date each other' when they appeared on the cover of the magazine together in November 2001. 

She turned 20 on September 4, 2001. She told Seventeen magazine in 2008: 'I was 18 when we first met, 19 when we first started dating.' 

They reportedly had a 'friendship' for a year before. Resurfaced photos, believed to be taken on the set of Destiny's Child's video for 'No, No, No', show the rapper aged 28 with his future wife two months after she turned 16. 

There is no suggestion of any relationship between them at the time.

The 'Cowboy Carter' singer told Oprah Winfrey in a 2013 interview she met Jay-Z in 2000 when she was 18 and the rapper was 30.

'We were friends first for a year and a half before we went on any date, on the phone for a year and a half, and that foundation is so important in a relationship,' the songstress said. 

'Just to have someone that you just like is so important, and someone that is honest.' 

The pair married in April 4, 2008 and have three children together — Blue Ivy, 12, and 7-year old twins Rumi and Sir. 

But before he became a family man, Jay-Z was reportedly playing the field in the early aughts and was rumored to have had a brief tryst with Rosario Dawson. 

Karrine Steffans, who was known by her nickname 'Superhead', openly discussed her sexual encounter with the 'Empire State of Mind' rapper in 2000.

'We only had one encounter that was beyond a friendship,' Steffans told DJ Vlad in an interview. 

'You're around someone so much and there is this tension. You want to, and you try it, and it just doesn't.' 

Steffans said after their encounter, she realized the sexual relationship with Jay-Z 'just doesn't work' but they 'remained cool'.

Steffans wrote about her encounters with various celebrities in her best-selling 2005 book Confessions of a Video Vixen. 

Rapper Charli Baltimore was another rumored former girlfriend whom Jay-Z was linked to in the late 1990s to possibly 2000. 

While not much is known about that relationship, Baltimore dispelled rumors that Jay-Z allegedly stabbed another man because of her.

'Let's be realistic,' Baltimore said in an interview on Vlad TV. 'Do you really think that these men with great careers are running around stabbing people over me? That sounds insane.' 

Carmen Bryan, who dated the 'Empire State of Mind' rapper from 1997 to 1999, has said in interviews that she was the reason for the rapper's infamous beef with Nas. 

Bryan, who has a daughter with Nas, said she got into a relationship with Jay-Z after she broke up with Nas. 

Bryan revealed she had become pregnant with Jay-Z, but had miscarried. 

'He can be very insecure,' Bryant said of Jay-Z in an interview. 'He has a little bit of a low self-esteem in certain areas. He's sensitive... We all have sensitivities. We all have things about us that we don't necessarily want the public to know about.'

In a stunning statement released to DailyMail.com, Jay-Z defended himself against the allegations filed by the unnamed woman who claimed she was raped by the rapper and Combs. 

He also blasted Texas-based attorney Tony Buzbee, who is representing the alleged victim.

'My lawyer received a blackmail attempt, called a demand letter, from a "lawyer named Tony Buzbee. What he had calculated was the nature of these allegations and the public scrutiny would me me want to settle. No sir, it had the opposite effect! It made me want to expose you for the fraud you are in a VERY public fashion. So no, I will not give you ONE RED PENNY!!'" 

In the meantime, the Cater family showed a united front as Jay-Z, Beyoncé and their daughter Blue Ivy appeared Monday night at the 'Mufasa' premiere — the highly anticipated prequel to 'The Lion King' — the at the Dolby Theatre in Hollywood.

In his letter, Jay-Z revealed his 'only heartbreak' was for his family amidst the damning rape allegations.

'My wife and I will have to sit out children down, one of whom is at the age where her friends will surely see the press and ask questions about the nature of these claims, and explain the cruelty and greed of people.'  

Jay-Z has filed a motion to dismiss the civil suit against him that was filed by Jane Doe. 

Buzbee filed his own action against Jay-Z and said, 'The pleading speaks for itself. This is a very serious matter that will be litigated in court.' 

Meanwhile, Combs remains in a Brooklyn jail and has separately been charged with sex trafficking and racketeering.

Federal prosecutors allege that Combs, 55, sexually abused women and coerced them into drug-fueled 'freak off' sex parties and used threats and violence against his alleged victims.

He has pleaded not guilty to all charges, and his criminal trial is currently slated to begin May 2025.