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Inside Diddy's stormy 11-year relationship with Cassie as slew of allegations made against music mogul

Through the lawsuit, Cassie Ventura shed light on allegedly dark aspects of her relationship with Diddy
PUBLISHED NOV 17, 2023
Singer Cassie Ventura had more than a decade-long roller-coaster relationship with rapper Diddy (Getty Images)
Singer Cassie Ventura had more than a decade-long roller-coaster relationship with rapper Diddy (Getty Images)

LOS ANGELES, CALIFORNIA: Singer Cassandra ‘Cassie’ Ventura recently filed a lawsuit against her former boyfriend Diddy, whose real name is Sean Combs.

In the lawsuit filed on Thursday, November 16, Cassie accused the founder of Bad Boy Records of rape, sexual battery, and violence among several allegations.

Before their final break up in 2018, the power couple was once in a more than a decade-long roller-coaster relationship. Through the lawsuit, Cassie, however, shed light on several allegedly dark aspects of their relationship.

Cassie accuses Sean Combs of rape and years of abuse in a lawsuit where the R&B singer claims that Mr. Combs, aka, Puff Daddy or Diddy, subjected her to a decade-long pattern of control and abuse.  (@diddy/Instagram, @cassie/Instagram)
Cassie Ventura has accused Sean Combs of rape and years of abuse in a lawsuit (@diddy, @cassie/Instagram)

Cassie Ventura is 'ready to tell' her story

Cassie wrote in the lawsuit, “After years in silence and darkness,” and added, “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,” per The New York Times.

Cassie Ventura and Diddy's relationship timeline

2007

While the duo first met in 2005, and as per the lawsuit, she signed with Bad Boy Records in 2006, the romance rumor did not start until 2007. In 2007, Cassie became the spokesmodel for Diddy's fashion line Sean John.

However, their relationship reportedly started after Diddy broke up with his on-and-off girlfriend Kim Porter in 2009, per Billboard.

2012

Cassie and Diddy went public with their relationship in 2012 as they made several public appearances together. They also attended Kanye West's Paris Fashion Week in 2012.

October 2013

In an interview with Madame Noir, Cassie opened up about her relationship with Diddy. Saying that "honesty and communication," is the key to any relationship, she described her relationship with Diddy that “just being around him is a completely inspiring experience.”

February 2014

At around this time, the couple were speculated to be engaged. Diddy posted the picture of a huge diamond ring and wrote, “Baby do you like it? I just want to get you wat you Like! I just wanna Mk you smile 🙂 #takeDat!” per Us Weekly.

While Diddy’s representative did not confirm the engagement, Cassie was seen wearing the diamond ring. 

December 2015

Diddy and Cassie allegedly broke up once in December 2015. Rumors of their break up started circulating when the ‘Paradise’ songstress shared a post on her Instagram.

She posted a sleeping baby meme that wrote, “How I sleep … knowing that I’m single and nobody cheating on me.”

She, however, soon deleted the post, reported Us Weekly.

It was rumored that the duo broke up. They, nevertheless, got back together shortly.

July 2016

In July 2016, Page Six reported that Cassie was “getting very flirty with another guy” during a party for the app MeWe at the Warwick in LA.

A witness told the news outlet, “She was looking this one guy up and down, giving him the flirty eye,” before adding, “She was acting very much like a single woman on the prowl.”

August 2016

The couple allegedly broke up in August 2016. TMZ reported at that time that Diddy got pissed off at her when Cassie purportedly told him that she wanted to break up.

It was said that Diddy got enraged and started scrolling through her phone. He also went away with her phone.

As Cassie went to her home, her mother called the police. In the meantime, Diddy however returned the phone to Cassie.

It was reported that the cops, upon arriving, took note of the domestic incident. But no charges were filed.

They got back together soon after.

May 2018

In May 2018, Cassie made her last Instagram post about Diddy in May. The couple attended the Met Gala in May 2018 together.

August 2018

Diddy made his last Instagram post about Cassie. In August, while wishing the songstress on her birthday, Diddy captioned, “Go BEST FRIEND ! ITS YOUR BIRTHDAY — HAPPY BIRTHDAY to MY LOVE ?? @cassie LOVE YOU 4eva #CassieDay,” per Billboard.

October 2018

Around mid-October 2018, news broke that Cassie and Diddy’s relationship came to an end. Initially, it was rumored that the music mogul cheated on Cassie with a Canadian model Jocelyn Chew.

However, during that time, a source told Hollywood Life, that tension brewed between the couple even before that. 

The source said “Cassie got tired of waiting for Diddy to put a ring on it. That was a big source of their issues and arguments,” before adding, “He always told her he wasn’t ready but he did leave room for her to believe that eventually the ring would come. But it never did.”

A few days after the rumor of their split broke, Combs posted a cryptic motivational quote on his Instagram, where he wrote, “I’m at a place in my life where my peace and happiness are my top priorities.”

He added, “I avoid placing myself around negative energy,” per Capital XTRA.

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