How old was Cassie when she started dating Diddy? Age difference explored in wake of severe abuse allegations

American singer, songwriter, model, actress, and dancer Cassie recently made headlines after she filed a lawsuit against former boyfriend, rapper, and hip-hop icon Sean ‘Diddy’ Combs for alleged serial physical abuse, s*xual slavery, and r*pe, as reported by Reuters.

Trigger Warning: The following article contains details related to physical and s*xual assault. Reader’s discretion is advised.

The lawsuit was filed on Thursday, November 16, at the U.S. District Court in Manhattan that claimed that Diddy forced Cassie to perform s*xual acts with hired male prostitutes, as he watched and filmed them for his entertainment. Besides, the lawsuit also accused Diddy of keeping her under the constant influence of drugs and alcohol for his benefit.

In the wake of these severe abuse allegations, the timeline of Cassie and Diddy’s relationship has come under scrutiny. Cassie started dating Diddy in 2007 when she was 21 years old.

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Cassie and Diddy were in an on-and-off relationship from 2007 to 2018

According to Uproxx, the now 37-year-old, Cassie first met Diddy when she signed with the latter’s record label Bad Boy in 2006 and released her eponymous debut album. It contained hit singles including Long Way 2 Go and Me & U. In fact, Diddy produced a remix of the second number. She was 19 years old at that time, while Diddy was 37.

The following year, Cassie turned spokesmodel for Diddy’s fashion label Sean John, which is when the rumors of their dating started. However, back then, the pair denied any link-ups, even though they were often spotted together in public.

Fast forward to 2012, Cassie and Diddy attended back-to-back events and parties including Kanye West’s Paris Fashion Week show, while holding hands, and allegedly going public with their relationship. The next year, Cassie said during an interview with Madame Noire that just being around Diddy was “a completely inspiring experience.” In the same interview, she credited Diddy for encouraging her to launch her own business venture.

In 2014, Diddy posted a picture of a diamond ring on Instagram (now deleted) with the caption “Baby do you like it? I just want to give you what you like!” While Diddy’s representative denied any rumors of an engagement, around the same time Cassie was spotted wearing the same ring, further fuelling speculations.

The following year in 2015, rumors arose that the couple allegedly broke up but reconnected soon after. The next year, media reports arose that they split up once again following a heated argument. Back then, TMZ reported that cops visited Cassie’s residence and even though none of them were charged with a crime, an alleged domestic violence report was filed. In 2018, Cassie and Diddy finally broke up citing undisclosed reasons.

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Exploring Cassie’s lawsuit against Diddy

On November 16, 2023, Cassie, whose real name is Casandra Elizabeth Ventura, filed a lawsuit against former longtime boyfriend Sean ‘Diddy’ Combs in the Federal District Court in Manhattan, under the Adult Survivors Act. As per this New York law, victims of s*xual abuse can file civil lawsuits after the “statute of limitations” has expired, stated the New York Times.

As per Casandra’s lawsuit, Diddy subjected her to years of physical and emotional abuse. The Official Girl singer alleged Diddy of regularly beating her over the course of a decade-long professional and romantic association. She also accused Diddy of forcing her into s*xual slavery with hired male prostitutes while making s*x tapes from them for his own pleasure.

Diddy has also been sued for allegedly r*ping Casandra towards the end of their relationship in 2018 when she decided to leave him, alongside intimidating her through forceful drug and alcohol intoxication. In short, the lawsuit portrayed Sean Combs as “an erratic, controlling individual, with violent tendencies,” as reported by Reuters.

The bombshell accusations also include Diddy pressuring Casandra to carry his firearm in her purse, assaulting her friends by dangling her over a high-rise hotel suite balcony, and blowing up the car of rapper Kid Cudi (he confirmed the same to New York Times), when he heard rumors that Cudi was allegedly interested in his girlfriend.

Ventura has demanded “justice for the decade of her life that Mr. Combs took away from her with threats of violence, excessive use of drugs, physical and psychological abuse, and s*xual slavery,” through her lawsuit, as revealed by Reuters. Violations of s*x and human trafficking laws have also been filed against Diddy.

Casandra told the New York Times in a statement that after “years in silence and darkness,” she was “finally ready to tell my story, and speak up on behalf of myself and for the benefit of other women who face violence and abuse in their relationships.”

Meanwhile, The Guardian states that Diddy’s security guard and assistants were witnesses to the daily tortures he inflicted on Casandra.

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Diddy maintains a not-guilty status

The 54-year-old Diddy has not issued a public statement so far about the explosive accusations. However, his attorney Ben Brafman told reporters on Thursday that his client “vehemently denies these offensive and outrageous allegations.

He also added that the lawsuit was “riddled with baseless and outrageous lies,” and was aimed at ruining the reputation of his client and “seeking a payday.” In fact, he counter-accused Casandra Ventura of blackmailing his client into paying her $30 million and threatening to “write a damaging book about their relationship.”

In contrast, Ventura’s attorney told the New York Times that she was offered eight-figures in exchange for her silence and to prevent the filing of the lawsuit.

Interestingly, Diddy is the latest high-profile figure in the music and record producing industry to have been accused of s*xual misconduct. Previously, the likes of Steven Tyler, L.A. Reid, and Neil Portnow have also been sued.