How long did Sean ‘Diddy’ Combs date Cassie? Exploring relationship timeline amid abuse allegations

Amid the rape and abuse allegations, let’s explore the relationship timeline between American rapper Sean Diddy Combs and his ex-girlfriend Cassie through the years

Published on Nov 18, 2023   |  10:58 AM IST  |  51.5K
‘Diddy’ Combs date Cassie ( IMDb )
Key Highlight
  • Diddy and Cassie started dating in 2007 till 2018
  • Cassie has accused Diddy of abuse, sex trafficking and rape
  • Diddy has refuted the claims made by his ex-girlfriend for now

Trigger warning: The article contains references to rape, sex trafficking and abuse

The recent accusations made by American singer and model Cassandra Elizabeth Ventura, popularly known as Cassie against her former ex-boyfriend rapper and music producer Sean ‘Diddy’ Combs has raised a lot of eyebrows and made the media take notice.

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The Love a Loser singer has filed some serious allegations against her former boyfriend, accusing him of sex trafficking, years of abuse, torture and rape. These serious allegations have been initially denied by the Coming Home singer making way for an upcoming legal battle between the former lovers. 

Let’s look at the couple’s history and see when they started dating and the way things soured between them.

 ‘Diddy’ Combs date Cassie ( IMDb )

Diddy and Cassie’s initial years of dating

Cassandra Ventura or Cassie first burst onto the scene as an artist of note with her self-titled album in 2006 which was released under Diddy’s label Bad Boy Records.

The collaboration led to the two becoming friends and things started to get serious in 2007 when Cassie became the face of Diddy’s fashion label Sean John. In the same year, the I’ll Be Missing You singer split up with his partner Kim Porter, leading to romance rumors with his young protégé. Cassie was 19 at the time, almost 14 years younger than Diddy.


The couple were initially rumored to be together but the confirmation for the same came in 2012, when both of them were spotted in Kanye West’s Paris Fashion Week show, later followed by Diddy’s own Paris Fashion Week show.

Over the years, the couple had a tumultuous relationship, with the couple breaking and patching things up again and again. In 2014, there were engagement rumors between the two when Diddy posted a photo photo of a diamond ring on Instagram. The rapper later took the picture down.

Amid more rumors of cheating and many alleged fights, the couple finally called it quits in 2018, with both going their separate ways and finding other partners. Cassie married her personal trainer Alex Fine in September 2019 and seemed to have moved on quite well.

Diddy went on to have a daughter with cybersecurity professional and model Dana Tran in 2022. 

ALSO READ: Who is Justin Combs? 5 things to know about rapper Diddy's eldest son arrested for DUI

The allegations and lawsuit filed by Cassie against Diddy

Despite a tumultuous relationship of almost 11 years, the couple seemed to be quite amicable after their initial separation. Diddy even congratulated Cassie and her partner Alex Fine when they announced their engagement.

But things seemed to have turned sour in the recent months. Cassie accused Diddy of sex trafficking, continued abuse for years and rape in November 2023.

"After years in silence and darkness, 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. With the expiration of New York's Adult Survivors Act fast approaching, it became clear that this was an opportunity to speak up about the trauma I have experienced and that I will be recovering from for the rest of my life," Cassie issued a statement to highlight the accusations against Diddy.

The Last Night singer denied them through his lawyers calling the allegations offensive and outrageous.

Disclaimer: If you know someone who is struggling with abuse, please reach out and report about it. There are several helplines available for the same.

ALSO READ: What is Cassie suing Diddy for? A closer look at singer's allegations against billionaire music mogul

About The Author
Ritwik Arora
Ritwik Arora
Content Writer

An obsessive pop culture nerd, Ritwik


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