The Rise and Fall of Diddy and Cassie: Relationship Timeline

The Gist:

• Cassie and Diddy met when she was signed to Diddy’s label, Bad Boy Records.
• They dated officially from 2012–2018.
• In November 2023, Cassie filed a lawsuit against Diddy alleging rape and years of abuse.

Sean “Diddy” Combs and singer Casandra Ventura, known professionally as “Cassie,” had an up-and-down relationship spanning over a decade. But years later it comes out that it was more down than up.

On Nov. 16, 2023, The New York Times reported that Cassie filed a lawsuit against Diddy for “rape and years of abuse.”

What led to the lawsuit? Let’s take a look back at their relationship timeline.

Cassie and Diddy first met in 2005, and the singer eventually released her first album, “Cassie,” under Diddy’s record label, Bad Boy Records. At the time, Diddy was with his longtime partner, and mother of his children, Kim Porter.

In 2007, Cassie became a spokesmodel for Diddy’s well-known clothing brand, Sean John. At the time, rumors were going around that the pair were in a relationship, but Diddy was still on again, off again, with Kim until 2009.

Although Cassie and Diddy never publicly discussed their relationship, the pair arrived together at multiple public events including Kanye West’s Paris Fashion Week show in March of that year. This basically told us that they were together, without telling us that they were together.

The engagement rumors started flying when Cassie was seen out and about wearing a huge rock on her finger. Diddy further stirred the pot when he posted a picture of a diamond ring on Instagram and captioned it, “Baby do you like it? I just want to give you what you like!” (via Billboard).

Break up rumors started when Cassie posted a baby meme on Instagram writing, “How I sleep … knowing that I’m single and nobody cheating on me,” (via US Weekly). There were reports that Cassie was seen flirting with another man, but that the pair quickly got back together.