When did Cassie and Diddy get together? Relationship timeline explored amid Sean Combs trafficking trial

Sean "Diddy" Combs' trial for s*x trafficking and racketeering started on Monday, May 12, 2025, in New York City. On the second day of trial, May 13, key prosecution witness and the music mogul's ex-girlfriend, Cassie Ventura, took the stand against him.

Cassie is identified as "Victim-1" in the case's indictment. She previously accused the mogul of s*xual and physical abuse during their time together in a civil lawsuit in 2023. On Tuesday, she testified about how the mogul reportedly controlled her from the start of their relationship. She also detailed how his dr*g-fuelled "freak offs" became a job for her.

Cassie and Diddy got together in 2007, around the time the music mogul ended his on-again, off-again relationship with Kim Porter, and a year after Cassie was signed to his music label, Bad Boy Records. However, they called it quits in October 2018.

Cassie Ventura's testimony on Tuesday followed accounts from two other witnesses: LAPD officer and California hotel security Israel Florez and male escort Daniel Phillip.

Cassie Ventura and Sean "Diddy" Combs dated from 2007 to 2018

Cassie Ventura and Sean "Diddy" Combs reportedly met in 2005, per her civil lawsuit against the music mogul. She was only 19 at the time, and a year later, in 2006, she released her self-titled album via Combs' record label, Bad Boy Records. However, according to Cassie, they started in a platonic relationship.

2007

Things changed when she turned 21. She said during her testimony on Tuesday, May 13, 2025, that during her birthday celebration in Las Vegas in 2007, Combs kissed her for the first time. That same year, Diddy split with his longtime on-again, off-again partner, Kim Porter. Shortly after that, the music mogul reportedly started inviting her to New York hotel rooms where he was staying.

During one of those visits, Cassie Ventura said in her testimony that the music mogul would perform oral s*x on her and make her "feel crazy" for not reciprocating. She also testified that she was s*xually inexperienced at the start of their relationship. She also mentioned that they had s*x during a Miami trip where she and Diddy wined and dined, and he gave her ecs**cy for the first time.

2012

While the two have been dating since 2007, it was only in 2012 that they made the relationship official to the public. They attended the Paris Fashion Week in March 2012 and joined the star-studded GQ Men of the Year Party in Los Angeles in November of that same year.

Also in 2012, engagement rumors started after Cassie shared a since-deleted Instagram photo of her left hand sporting a diamond ring, per E! News at the time. Around two years later, Diddy reignited the engagement rumor after posting a since-deleted Instagram picture of a diamond ring for Valentine's Day, per another report by the outlet.

2018

Six years later, in January 2018, he hinted in an interview with Power 105.1 FM's The Breakfast Club that he wanted to have kids with her. He said:

"I'm trying to get to 10 [kids]. It's a race. I could get to eight without a problem. I could go to eight real quick... I would only have [more children] with my girl, of course."

However, months after that, in October, Cassie's representative confirmed to LoveBScott, per Today, that she and Diddy were no longer together.

Cassie Ventura married Alex Fine in 2019, and they welcomed their first child in December that same year. Their second daughter was born in 2021, and she's currently pregnant with their third child as she takes the stand against Diddy.

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