Sean ‘Diddy’ Combs and Ex Cassie’s Relationship Timeline

Nicholas Hunt/Getty ImagesSean “Diddy” Combs and ex-girlfriend Cassie weathered many ups and downs during their romance before parting ways for good in 2018. While Cassie (real name Cassandra Ventura) has since married Alex Fine and become a mother, her relationship with Diddy hasn’t stopped making headlines. The New York Times reported in November 2023 that Cassie filed a lawsuit against Diddy claiming the music mogul had a history of abuse while they were together. Cassie alleged in court documents obtained by the outlet that Diddy urged her to take drugs, beat her and forced her to have sex with “male sex workers” while “filming the encounters.” She further claimed that Diddy “forced her into her home and raped her” in 2018. Related: Hollywood's Sexual Misconduct Scandals While Hollywood may appear to be all glitz and glam on the surface, the industry has seen its fair share of scandals through the years. The New York Times and the New Yorker fir

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Sean ‘Diddy’ Combs and Ex Cassie’s Relationship Timeline
Sean Diddy Combs and Ex Girlfriend Cassie s Relationship Ups and Downs A Timeline 226
Nicholas Hunt/Getty Images

Sean “Diddy” Combs and ex-girlfriend Cassie weathered many ups and downs during their romance before parting ways for good in 2018.

While Cassie (real name Cassandra Ventura) has since married Alex Fine and become a mother, her relationship with Diddy hasn’t stopped making headlines. The New York Times reported in November 2023 that Cassie filed a lawsuit against Diddy claiming the music mogul had a history of abuse while they were together.

Cassie alleged in court documents obtained by the outlet that Diddy urged her to take drugs, beat her and forced her to have sex with “male sex workers” while “filming the encounters.” She further claimed that Diddy “forced her into her home and raped her” in 2018.

Jeremy Piven, Harvey Weinstein, Kevin Spacey, Sexual Misconduct, Hollywood, Sexual Harassment
While Hollywood may appear to be all glitz and glam on the surface, the industry has seen its fair share of scandals through the years. The New York Times and the New Yorker first published investigative pieces in 2017 that accused disgruntled movie producer Harvey Weinstein of decades of sexual assault and harassment. Soon after, Weinstein stood trial and was […]

Diddy “vehemently” denied the allegations at the time, calling them “offensive and outrageous” in a statement to The New York Times.

Scroll down to see Diddy and Cassie’s relationship highs and lows:

2007

The pair first met in 2005 and two years later they were romantically linked. Diddy and Cassie’s relationship began after the “I’ll Be Missing You” rapper split from Kim Porter, with whom he shares four children: stepson Quincy, son Christian and twin daughters D’Lila and Jessie. (Diddy also shares son Justin with his high school sweetheart Misa Hylton-Brim and daughter Chance with ex Sarah Chapman.)

Sean Diddy Combs and Ex Girlfriend Cassie s Relationship Ups and Downs A Timeline 224
Jamie McCarthy/WireImage

2012

Cassie and Diddy publicly confirmed their relationship by attending several events together, including Kanye West’s Paris Fashion Week runway show that March.

February 2014

“Baby do you like it? I just want to get you wat you Like! I just wanna Mk you smile                             
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