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

Sean Diddy Combs and Ex Girlfriend Cassie s Relationship Ups and Downs A Timeline 226
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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.

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.

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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. In March 2024, his Los Angeles and Miami homes were investigated by the U.S. Department of Homeland Security in connection to a federal sex trafficking investigation.

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


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.)

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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 🙂 #takeDat!” Diddy captioned an Instagram photo of a diamond ring, sparking engagement speculation. Cassie was later seen wearing the rock, but neither party ever confirmed an engagement.

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December 2015

Rumors that the pair called it quits surfaced after Cassie posted a photo of a sleeping baby meme on Instagram that read, “How I sleep … knowing that I’m single and nobody cheating on me.” She quickly deleted the post.

August 2016

Following a headline-making argument in Beverly Hills, the couple once again sparked breakup rumors. However, Us Weekly exclusively confirmed at the time that Cassie and Diddy were still together and the altercation was just an argument.

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Larry Busacca/Getty Images

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 is supposed to happen in the future is going to happen, but that’s something that I want. I would only have it with my girl [Cassie], of course.”

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John Shearer/Getty Images for The Hollywood Reporter

October 2018

Less than one year later, news broke that Cassie and Diddy had parted ways for good. “They are indeed no longer together and haven’t been for months,” Cassie’s rep said in a statement to LoveBScott at the time. The split announcement came one month after Diddy was spotted with model Jocelyn Chew in Miami.

January 2019

Cassie moved on with personal trainer Fine, which a source told Us was a blow for Diddy, who originally hired Fine to work with the singer. “Diddy’s ego wasn’t just shot,” the insider claimed to Us. “This is their realest breakup … They were in love for many years. They were in a very real relationship for over a decade. They broke up and always got back together.”

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Johnny Nunez/WireImage

June 2019

After Cassie announced she was expecting her first baby with Fine, Diddy sent his well-wishes via social media. “Congratulations @Cassie and Alex,” Diddy captioned a photo of the pair via Instagram. “I wish you all nothing but love and happiness. God bless ❤️❤️❤️ L O V E.”

September 2019

Diddy shared a cryptic message via Instagram after news broke that Cassie and Fine tied the knot. “Keep Going. I’ve 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.

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Jeff Vespa/Getty Images For GQ

November 2023

“After years in silence and darkness,” Cassie said in a statement to 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 speak up on behalf of myself and for the benefit of other women who face violence and abuse in their relationships.”

Diddy, meanwhile, issued a statement of denial via his legal team that same day. “Mr. Combs vehemently denies these offensive and outrageous allegations. For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail,” 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 riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs’s reputation and seeking a payday.”

Cassie’s legal team, for its part, claimed that Diddy offered her “eight figures to silence her,” which she rejected. Instead, she sued her ex-boyfriend for allegedly harming her in the past both physically and sexually.

She alleged in the lawsuit that when she dated rapper Kid Cudi in 2012, Diddy got so angry 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 the NY Times that Cassie’s account of the story was “all true.”

One day after filing the lawsuit, Cassie confirmed to Us that she and Diddy had reached a settlement.

“I have decided to resolve this matter amicably on terms that I have some level of control over,” the singer said in a November 17 statement distributed by her attorney Doug Wigdor. “I want to thank my family, fans and lawyers for their unwavering support.”

Diddy also released a statement through Wigdor, sharing that they had decided to resolve the matter “amicably.”

March 2024

After facing more sexual assault and harassment lawsuits from multiple people, Diddy became the target of a U.S. Department of Homeland Security sex trafficking investigation. His properties across the country were raided.

“Earlier today, Homeland Security Investigations New York executed law enforcement actions as part of an ongoing investigation with assistance from HSI Los Angeles, HSI Miami and our local law enforcement partners,” Homeland Security shared in a statement with Us. “We will provide further information as it becomes available.”

Two of Diddy’s sons, Justin and King, were reportedly detained and later released as his Beverly Hills home was searched. Following the raids, Diddy was spotted pacing at a Miami airport. According to TMZ, he and his entourage were allegedly stopped from taking off in a private jet by Homeland Security. Diddy did not publicly address the raids at the time.

While it is unknown whether Cassie’s settled lawsuit against the music star is connected to the federal investigation, her lawyer Douglas Wigdor told Us in a statement that they “will always support law enforcement when it seeks to prosecute those that have violated the law.” The statement continued: “Hopefully, this is the beginning of a process that will hold Mr. Combs responsible for his depraved conduct.”

May 2024

CNN obtained security footage taken in 2016 that allegedly showed Diddy grabbing Cassie by her neck at the now-closed InterContinental Hotel in Los Angeles before he shoved, dragged and kicked her. He also allegedly threw an object at Cassie before walking away.

“The gut-wrenching video has only further confirmed the disturbing and predatory behavior of Mr. Combs,” Cassie’s attorney Wigdor told Us in a statement after the footage resurfaced. “Words cannot express the courage and fortitude that Ms. Ventura has shown in coming forward to bring this to light.”

Diddy has not addressed the video clip. Us reached out for comment.

If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673).

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