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Diddy and Cassie’s Relationship Timeline: From Dating to Her Testimony in Hip-Hop Mogul’s Trial

Brianna Sainez

Published

1 year ago

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cassie diddy
Cassie Ventura and Sean Diddy Combs.

Cassie first met Bad Boy Records mogul Sean “Diddy” Combs at just 19 years old as she was launching her music career.

Nearly a decade later, the recording artist spoke out against the alleged violence she experienced while dating her record label-owning ex at his federal sex trafficking trial in May 2025.

In Touch breaks down Cassie and Diddy’s relationship timeline and how they went from a couple sitting front row at Fashion Week to being thrust back into the spotlight due to serious allegations against the hip-hop mogul and her bombshell testimony.

Combs has denied all allegations and pled not guilty to all charges.

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