The world of celebrity relationships is often shrouded in mystery, with fans eagerly trying to piece together the timelines of their favorite stars’ romantic histories. One such notable couple in the music and entertainment industry was Sean “Diddy” Combs and Cassie Ventura.

Cassandra Ventura, also known as Cassie, debuted as a notable musician in 2006 with her self-titled album, which was released on Diddy’s company Bad Boy Records.

In this article, we’ll delve into the beginnings of their relationship, tracing the timeline of when Diddy and Cassie started dating.

Cassie and Diddy’s Love Story

Cassie and Diddy became friends as a result of their cooperation, and things became more serious in 2007 when Cassie became the face of Diddy’s fashion line Sean John.

The I’ll Be Missing You singer parted up with his partner Kim Porter the same year, sparking romance suspicions with his teenage protégé. Cassie was 19 years old at the time, over 14 years younger than Diddy.

The duo was previously speculated to be dating, but their relationship was confirmed in 2012, when they were both sighted in Kanye West’s Paris Fashion Week show, followed by Diddy’s own Paris Fashion Week show.

The pair’s relationship was turbulent throughout the years, with the couple repeatedly breaking up and patching things up. When Diddy uploaded a photo of a diamond ring on Instagram in 2014, it sparked engagement speculations between the two. The rapper later removed the photo.

Amid more suspicions of adultery and numerous purported confrontations, the pair finally called it quits in 2018, splitting up and finding new partners. Cassie married her personal trainer Alex OK in September 2019 and appeared to be doing OK.

In 2022, Diddy will have a daughter with cybersecurity professional and model Dana Tran.

Is Cassie and Diddy Engaged?

Cassie was seen out and about with a large rock on her finger, which sparked engagement speculations.

Diddy added fuel to the fire by posting a photo of a diamond ring on Instagram with the message, “Baby, do you like it?” I simply want to give you what you want!” (Image courtesy of Billboard).

Why Did Cassie File a Lawsuit Against Diddy?

Despite a turbulent 11-year relationship, the pair appeared to be amicable after their initial split. When Cassie and her partner Alex Fine announced their engagement, Diddy congratulated them.

However, things appeared to have soured in recent months. Cassie accused Diddy of sex trafficking, years of abuse, and rape in November 2023.

“After years of silence and darkness, I am finally ready to tell my story and speak up for myself and other women who face violence and abuse in their relationships.” “With the expiration of New York’s Adult Survivors Act quickly 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 said in a statement highlighting Diddy’s allegations.

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The Last Night singer disputed the charges through his lawyers, calling them disrespectful and preposterous.