Sean Combs and Cassie Ventura: A Journey Through Their Relationship Timeline
Sean ‘Diddy’ Combs and Cassie had an on-again, off-again relationship for over a decade before parting ways in October 2018 Their journey together spanned from 2007 to 2018, with notable milestones in 2012, February 2014, December 2015, August 2016, January 2018, and finally their split in October 2018
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Sean “Diddy” Combs and ex-girlfriend Cassie weathered many ups and downs during their romance before parting ways for good in 2018.
Despite Cassie (also known as Cassandra Ventura) marrying Alex Fine and becoming a mother, her association with Diddy continues to generate headlines. The New York Times reported in November 2023 that Cassie took legal action against Diddy, accusing the music mogul of a history of abuse during their relationship.
According to court documents obtained by the outlet, Cassie asserted that Diddy coerced her into using drugs, physically assaulted her, and compelled her to engage in sexual activities with "male sex workers" while recording the encounters. Additionally, she alleged that Diddy sexually assaulted her in her own residence in 2018.
Diddy adamantly refuted the accusations, deeming them as "offensive and shocking" in a statement provided to The New York Times.
Please continue scrolling to explore the ups and downs of Diddy and Cassie's relationship.
2007
The pair crossed paths for the first time in 2005, and two years down the line, they became romantically involved. Diddy and Cassie's relationship commenced subsequent to the "I'll Be Missing You" rapper's separation from Kim Porter, the mother of his four children: stepson Quincy, son Christian, and twin daughters D'Lila and Jessie. (Furthermore, Diddy shares a son named Justin with his high school sweetheart Misa Hylton-Brim and a daughter named Chance with ex Sarah Chapman.)
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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
December 2015
Diddy posted a photo on Instagram captioned with the question "Baby do you like it? I just want to get you what you like! I just wanna make you smile #takeDat!" The caption accompanied a picture of a diamond ring, which led to speculation about an engagement. Although Cassie was later seen wearing the ring, neither Diddy nor Cassie confirmed any plans to marry.
Rumors of their breakup began circulating when Cassie shared a meme on Instagram featuring a sleeping baby with the caption, "How I sleep... knowing I'm single and no one is cheating on me." However, she swiftly removed the post.
August 2016
Following a highly publicized altercation in Beverly Hills, the couple ignited further speculation about a potential split. However, We have exclusively verified that Cassie and Diddy remained in a committed relationship, with the incident being nothing more than a heated argument.
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January 2018
During an interview on Power 105.1 FM's The Breakfast Club, Diddy expressed his love for children and his desire to have a total of 10. He stated that whatever the future holds, he would only have more children with his partner, Cassie.
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October 2018
January 2019
Less than a year later, it was announced that Cassie and Diddy had officially ended their relationship. According to a statement from Cassie's representative to LoveBScott at the time, they had been separated for several months. Interestingly, the news of their split emerged just one month after Diddy was seen with model Jocelyn Chew in Miami.
January 2019
Cassie's decision to move on with her personal trainer, Fine, reportedly came as a blow to Diddy. Initially, Diddy had hired Fine to work with the singer. According to an insider, Diddy's ego suffered greatly from this situation. The source further shared that this breakup is the most genuine one between them. Cassie and Diddy had been in love for many years and their relationship lasted over a decade. Despite previous breakups, they had always managed to reconcile.
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June 2019
Following Cassie's announcement of her first pregnancy with Fine, Diddy expressed his congratulations through social media. "Congratulations @Cassie and Alex," Diddy wrote as the caption accompanying a photo of the couple on Instagram. "I send you nothing but love and happiness. May God bless you with abundant L O V E."
September 2019
Following the revelation that Cassie and Fine had gotten married, Diddy took to Instagram to share a mysterious message. The quote, which read "Keep Going. I've got you. - The Universe," hinted at an encouraging sentiment. Not long after, Cassie gave birth to Frankie, their first daughter. Fast forward to March 2021, and the family extended their joy with the arrival of their second daughter, Sunny.
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November 2023
"After enduring years of silence and darkness," Cassie stated to The New York Times following the filing of a groundbreaking lawsuit against Diddy, accusing him of abuse and assault. "I am finally prepared to share my story and speak out not only for myself, but also for the countless women who suffer violence and abuse in their own relationships."
In response to the allegations, Diddy released a statement through his legal team denying the claims. "Mr. Combs adamantly rejects these offensive and shocking accusations. Over the past six months, Ms. Ventura has relentlessly demanded $30 million from him, threatening to publish a damaging book about their relationship. This attempt at blatant blackmail was unequivocally rejected," stated his lawyer, Ben Brafman. "Despite retracting her initial threat, Ms. Ventura has now resorted to submitting a lawsuit filled with baseless and outrageous falsehoods, with the aim of tarnishing Mr. Combs's reputation and seeking financial gain."
Cassie's legal team, on their behalf, asserted that Diddy attempted to bribe her with a substantial sum of money to prevent her from speaking out, a proposition she declined. Instead, she pursued legal action against her former boyfriend, accusing him of perpetrating physical and sexual harm in the past.
According to the lawsuit, during her relationship with rapper Kid Cudi in 2012, Diddy became so enraged that he threatened to detonate the musician's car. "Around that time, Kid Cudi's car was destroyed by an explosion in his driveway," as stated in the legal documents. Kid Cudi confirmed to the NY Times that Cassie's version of events was "completely accurate."
If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673).
