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Sean ‘Diddy’ Combs and Cassie’s complete relationship timeline

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Ventura accused Combs of trafficking, rape and physical abuse in a bombshell lawsuit filed in November 2023.
Cassie and Sean “Diddy” Combs dated for more than a decade on-and-off before their split in 2018.
While the “Me & U” singer, 37, and the Ciroc founder, 54, had many ups and downs over the years, they both found other partners following their breakup.
Cassie, whose birth name is Casandra Ventura, tied the knot with fitness trainer Alex Fine in late 2019 after meeting a year prior. The pair are now parents of daughters Sunny and Frankie.
Combs, for his part, would go on to have romances with City Girls rapper Yung Miami and Dana Tran, whom he welcomed a child with in 2022.
One year later, the New York City native was sued by Ventura in November 2023, accusing him in a bombshell lawsuit of trafficking, rape and physical abuse.
“After years in silence and darkness, I am finally ready to tell my story, and to speak up on behalf of myself and for the benefit of other women who face violence and abuse in their relationships,” Ventura said in a statement via her attorneys at Wigdor LLP.
“Ms. Ventura has now fully escaped Mr. Combs, but the harm that the assaults and sexual abuse he caused her to experience for nearly a decade will forever haunt her,” the filing stated.
Combs has slammed the claims, with his attorney, Ben Brafman, saying that the rapper “vehemently denies these offensive and outrageous allegations.” He also alleged that Ventura had been demanding $30 million from Combs for the last six months “under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail.”
Keep reading to see Combs and Ventura’s full relationship timeline.2007
The former couple first locked eyes in 2005 and began dating two years later. The rapper had just broken up with late ex Kim Porter at the time.
Ventura was hired for Combs’ clothing line Sean John and was signed to his label, Bad Boy Records, in 2007.2012
Their relationship was confirmed when they stepped out for Kanye West’s Paris Fashion Week runway show in March.

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