Keeping up with Kim Kardashian and Ray J’s ongoing legal battle is easier said than done.
Although the pair split for good in 2006, their relationship continues to haunt them more than two decades later.
In March 2026, a California judge denied Kardashian’s request to seal a $6 million “confidential settlement agreement” with the singer related to their 2003 sex tape.
In the new ruling, obtained by Us Weekly, the court determined Kardashian and her mom, Kris Jenner, “have not met their burden” to support the requested sealing order. (Us has reached out to Kardashian and Ray J’s attorneys for comment.)
Kim Kardashian’s Dating History Through the Years
The ruling stems from Ray J’s November 2025 cross-complaint that he and Kardashian had agreed to a deal not to discuss their 2003 sex tape.
As court proceedings continue, Us Weekly is breaking down the complicated personal and legal history of Kardashian and Ray J below:
When Did Kim Kardashian and Ray J Date?
Kim Kardashian and Ray J met in 2002 amid the KKW Beauty founder’s divorce from ex-husband Damon Thomas. The former Keeping Up With the Kardashians star was relatively unknown at the time and was working for Ray J’s sister, Brandy, as a stylist.
The pair hit it off, with Ray J proclaiming that his then-girlfriend was going to be a star.
“It was so many different things about her,” he shared during a 2003 Vlad TV interview. “But let me say that beyond the love, I felt like she had star quality. And I felt like she could be really big. So it happened. I got a lot of respect for Kim.”
The two eventually split in late 2006.
When Did Kim Kardashian and Ray J’s Sex Tape Surface?
A sex tape of Kim Kardashian and Ray J emerged in February 2007. Adult entertainment company Vivid allegedly paid millions of dollars to obtain a copy of the video.
“We loved each other,” Ray J shared during a 2017 episode of Celebrity Big Brother when discussing his past romance with Kardashian. “Every relationship I was in, I loved the girl. It’s just the moral standards and values were off. I was loving and lying.”
Kim Kardashian and Ray J’s Alleged Secret Settlement
In March 2026, TMZ obtained a copy of an alleged secret settlement from Kim Kardashian and Ray J that prohibited either from dishing about their infamous sex tape.
“The parties have agreed to enter this agreement addressing all past, current or future claims, disputes, causes of action, defenses and alleged losses, including without limitation, all claims and defenses arising out of or concerning the subject matter of the sex tape,” the 2023 court documents stated.
According to TMZ, the contract was filed as part of a defamation lawsuit filed by Kim and her mom, Kris Jenner, against Ray J.
Kim Kardashian and Kris Jenner Sue Ray J for Defamation
According to court documents obtained by Us, Kim Kardashian’s attorney Alex Spiro filed a defamation lawsuit against Ray J in October 2025.
Kim and her mom, Kris Jenner, claimed in court documents that Ray J’s remarks about their family have created “substantial and ongoing harm to their personal and professional reputation.”
The mother-daughter duo also alleged that Ray J is “unable to accept the end of his fleeting relationship with Ms. Kardashian over 20 years ago.”
Kim and Ray J’s Relationship Timeline: From Sex Tape to Cheating Confessions
Ray J Responds to Kim Kardashian and Kris Jenner’s Lawsuit
In November 2025, Us confirmed that Ray J filed a countersuit against Kim Kardashian and Kris Jenner and claimed that the previous lawsuit was “not about defamation” but rather was about “publicity, power and punishment.”
In court documents, Ray J alleged that Kardashian and Jenner had spent “two decades peddling the false story” that the sex tape was “leaked against her will.”
In response to his countersuit, Jenner and Kardashian’s attorney told Us, “After realizing he is losing the case and losing his way, this disjointed rambling distraction is not intimidating anyone. Ray J will lose this frivolous case too.”
In separate court documents obtained by Us in March 2026, Kardashian and Jenner denied claims that the sex tape was a “staged event.”
“[Ray J’s] claim that I had a plan with my mother and others to release a sex tape, defraud the public and file a ‘fake’ lawsuit against the porn company that released it to ‘create buzz’ is a lie,” Kardashian said.
Jenner added that claims that she was in charge of the “release and commercial exploitation” of Kardashian’s sex tape are “absolutely false.”
