The relationship timeline of Sean ‘Diddy’ Combs and ex-girlfriend Cassie
Sean “Diddy” Combs and ex-girlfriend Cassie endured many ups and downs during their romance before splitting for good in 2018.
While Cassie (real name Cassandra Ventura) is now married Alex Fine and becoming 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 use drugs, hit her and forced her to have sex with “male sex workers” while they “filmed the encounters.” She further alleged that Diddy “forced his way into her house and raped her” in 2018.
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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 the highs and lows of Diddy and Cassie’s relationship:
2007
The couple first met in 2005 and were romantically linked two years later. Diddy and Cassie’s relationship began after the “I’ll Be Missing You” rapper split 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.)
2012
Cassie and Diddy publicly confirmed their relationship by attending several events together, including Kanye West’s catwalk show during Paris Fashion Week in March.
February 2014
“Honey do you like it? I just want to give you what you like! I just want to make you laugh 🙂 #takeDat!” Diddy captioned an Instagram photo of a diamond ring, sparking engagement speculation. Cassie was later seen wearing the stone, but neither party ever confirmed an engagement.
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December 2015
Rumors that the couple called it quits surfaced after Cassie posted a photo of a sleeping baby meme on Instagram with the caption, “How I sleep…knowing I’m single and no one is cheating on me.” She quickly deleted the message.
August 2016
After an argument in Beverly Hills, the couple once again sparked rumors of a breakup. However, We weekly exclusively confirmed at the time that Cassie and Diddy were still together and that the altercation was just an argument.
January 2018
“I love children. I’m trying to get 10,” Diddy revealed during an appearance on Power 105.1 FM’s The breakfast club. “Whatever needs to happen in the future will happen, but that’s something I want. I would only want it with my girl [Cassie]Naturally.”
October 2018
Less than a year later, news broke that Cassie and Diddy had split for good. “They are indeed no longer together and have not been for months,” Cassie’s rep said in a statement to LoveBScott at the time. The split announcement came a month after Diddy was spotted with model Jocelyn Chew in Miami.
January 2019
Cassie moved on with personal trainer Fine, a source said Us was a blow to Diddy, who originally hired Fine to work with the singer. “Diddy’s ego wasn’t just shot,” the insider claimed Us. “This is their most real breakup… They were in love for years. They had a very real relationship for over a decade. They broke up and always got back together.”
June 2019
After Cassie announced she was expecting her first child with Fine, Diddy sent his well wishes via social media. “Congratulations @Cassie and Alex,” Diddy captioned a photo of the couple via Instagram. “I wish you all nothing but love and happiness. God bless ❤️❤️❤️ LOVE E.”
September 2019
Diddy shared a cryptic message via Instagram after news broke that Cassie and Fine tied the knot. “Keep going. I got you. – The universe,” the quote read. Three months later, Cassie welcomed her and Fine’s first daughter, Frankie. The couple expanded their family in March 2021 with the arrival of daughter Sunny.
November 2023
“After years in silence and darkness,” Cassie said in a statement The New York Times after filing a bombshell lawsuit against Diddy for alleged abuse and assault. “I am finally ready to tell my story, and to stand up on my own behalf and on behalf of other women who experience violence and abuse in their relationships.”
Diddy issued a denial statement through his legal team that same day. “Mr. Combs vehemently denies these offensive and scandalous allegations. For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand for $30 million under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail,” says his lawyer. Ben Brafman said in a statement to the outlet. “Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit filled with baseless and outrageous lies in order to tarnish Mr. Combs’ reputation and seek a payday.”
Cassie’s legal team, in turn, claimed that Diddy offered her “eight figures to shut her up,” which she rejected. Instead, she sued her ex-boyfriend for allegedly harming her both physically and sexually in the past.
She claimed in the lawsuit that she was dating a rapper Kid Cudi in 2012, Diddy got so angry that he threatened to blow up the musician’s car. “Around that time, Kid Cudi’s car exploded in his driveway,” the documents state. Cudi told New York times that Cassie’s account of the story was “completely true.”
If you or someone you know has been sexually assaulted, please reach out the National Sexual Assault Hotline at 1-800-656-HOPE (4673).