Kim Kardashian, Ray J’s Relationship, Sex Tape Timeline

The drama never ends. Kim Kardashian and Ray J may have split in 2006, but their relationship continues to haunt them almost two decades later.

The former pair met in 2002 amid the KKW Beauty founder’s divorce from ex-husband Damon Thomas. Kardashian was relatively unknown at the time and was working for Ray J’s sister, Brandy, as a stylist.

The two hit it off immediately, and the “Sexy Can I” singer wasted no time in saying that he knew his girlfriend was destined for the spotlight.

“It was so many different things about her,” the artist confessed during a Vlad TV interview in 2003. “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.”

While the two split in late 2006, a sex tape of the former couple emerged in February of the following year. Adult entertainment company Vivid allegedly paid millions of dollars to obtain a copy of the video, with Kardashian suing them for $5 million for copyright rights.

During his time in 2017 on Celebrity Big Brother, the Love & Hip-Hop Hollywood alum opened up about his breakup with the Kardashians star.

“We loved each other. Every relationship I was in, I loved the girl. It’s just the moral standards and values were off. I was loving and lying,” he confessed during the 2017 episode of the show.

Trouble brewed again during an April 2022 episode of The Kardashians when the Skims founder claimed she was trying to access another explicit video amid allegations that there was previously unreleased footage. The following week, Kardashian revealed that estranged husband Kanye West delivered the entire tape to her after meeting with Ray J.

“So Kanye flew home last night, and he came back this morning. I want to show you guys what he got me. He got me all of the sex tape back,” the reality star explained. “He flew home, and he got the computer it was on and the hard drive. He met with Ray J at the airport, and he got it all back for me.”

The Mississippi native instantly retaliated against Kardashian’s claims, speaking with the Daily Mail in a May 2022 interview.

“I’ve sat in the shadows for over 14 years allowing the Kardashians to use my name, to abuse my name, make billions of dollars over a decade and a half talking about a topic I’ve never really spoken about,” the songwriter said. “I have never leaked a sex tape in my life. It has never been a leak.”

Ray J added: “I never had a single one at my house — she had them at her house. She’s always had all the tapes in a Nike shoe box under her bed. That’s how it all came about. Once I pitched the idea to her, just playing around a little bit, that’s when she jumped on the idea, talked to her mom and it was out of my hands from there.”

The “Wait a Minute” singer accused both Kardashian and Kris Jenner of orchestrating the leak. He also revealed alleged DMs between him and Kardashian that claimed everything shown on The Kardashians regarding the tape was a lie.

“Now I realize this is another promo stunt for you — unless you reach out to me soon I’m gonna take it to the level where it shows all of what we did,” Ray J wrote, per the screenshots. “All of the meetings and convos about the plan — date and times of our meetings and the whole lie you and Kris planned this since the beginning.”

Ray J went on to beg the reality star to “help him stay in a positive light” for his children.

“Please don’t make their dad look like a loser when you know me more,” he pleaded.

Kardashian allegedly replied with an apology, agreeing that “moving on” from the sex tape was best for everyone.

“I completely understand — and I appreciate hearing this from you,” she appears to have written. “I want you to know that I wish nothing but the best for you. This has hurt us both in so many ways and I know we are aligned in wanting to move forward in our lives. … Thank you for reaching out and my hope is that after next week when everyone sees that the computer was given back to Kanye that this story will be dead and done.”

Kardashian allegedly added: “I’m sorry to hear how this has affected you — that wasn’t my intention.”

The “Another Day in Paradise” singer has been vocal about his struggle with mental health following the sex tape leak telling the Daily Mail in May 2022 that he “felt suicidal because when you know something’s real and it’s true and you’re watching a whole family create an empire from a lie they’ve created, it’s heartbreaking and disrespectful.”

Scroll down and relive the former couple’s tumultuous relationship that has spanned two decades.