When Did Diddy and Cassie Break Up?

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Written By Ryan Johnson






Sean “Diddy” Combs and Cassie Ventura’s relationship spanned over a decade filled with ups and downs before their final breakup in 2018. Here is a detailed timeline of their relationship and eventual split.

2005: The Beginning

Diddy and Cassie met in 2005 when she was 19 and signed to his label, Bad Boy Records. Their professional relationship soon evolved into a romantic one.

2007: Romantic Links

By 2007, the pair were romantically linked, often seen together at various events, sparking rumors of a relationship.

2012: Public Confirmation

In 2012, Diddy and Cassie appeared together at high-profile events, such as Kanye West’s Paris Fashion Week show, confirming their romantic involvement.

Engagement Speculations

Throughout their relationship, rumors of engagement surfaced multiple times. In 2012, a photo of Cassie with a diamond ring and another in 2014 fueled these speculations, but neither confirmed an engagement.

2016: Breakup Rumors

In August 2016, following a public argument, breakup rumors spread. However, sources confirmed they were still together.

January 2018: Future Plans

In early 2018, Diddy expressed his desire to have children with Cassie during an interview, indicating a serious commitment.

October 2018: The Final Split

By October 2018, it was confirmed that Diddy and Cassie had officially broken up. Cassie’s representative stated that they had been separated for months.

Post-Breakup Developments

Cassie moved on with personal trainer Alex Fine in early 2019, whom she later married and had children with. Diddy publicly congratulated her on her new relationship and family.

Legal Battles and Allegations

November 2023: Cassie’s Lawsuit

Cassie filed a lawsuit against Diddy in November 2023, alleging years of abuse and rape. She claimed that Diddy controlled her through a drug-fueled lifestyle and forced sexual encounters. Diddy vehemently denied these allegations.

Settlement and Federal Investigation

Cassie and Diddy reached an amicable settlement in November 2023. Meanwhile, Diddy faced a federal investigation for sex trafficking, with raids conducted on his properties.


Diddy and Cassie’s relationship ended in 2018 after numerous highs and lows. Their breakup marked the end of a tumultuous chapter, leading to legal battles and significant public scrutiny in the following years.

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