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Sean 'Diddy' Combs and Cassie Ventura's Relationship: Everything to Know

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Sean 'Diddy' Combs and Casandra 'Cassie' Ventura had a tumultuous past relationship, which gained renewed attention amid his s-- trafficking trial.

May 26 2025, Published 9:45 a.m. ET

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2005: Sean 'Diddy' Combs and Cassie Ventura Met

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Sean 'Diddy' Combs and Cassie Ventura dated for over a decade.

Sean 'Diddy' Combs first met Casandra "Cassie" Ventura in 2005 when she was 19 years old. One year later, Ventura released her self-titled debut album under Combs' record label, Bad Boy Records.

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2007: Sean 'Diddy' Combs and Cassie Ventura Sparked Dating Rumors

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Sean 'Diddy' Combs dated Kim Porter before Cassie Ventura.

The twosome struck up a romance in 2007 following the "It's All About the Benjamins" rapper's split from Kim Porter, with whom he welcomed four kids: Quincy, Christian, D'Lila and Jessie. Diddy is also the father to Justin, Chance and Love Sean.

Amid the dating rumors, Diddy and Cassie maintained their silence over their relationship.

Meanwhile, Kim later confirmed she ended their on-again, off-again romance after 13 years of dating.

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2012: Sean 'Diddy' Combs and Cassie Ventura Seemingly Confirmed Their Romance

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Sean 'Diddy' Combs and Cassie Ventura kept a low-key relationship before making public appearances together.

In 2012, Diddy and Cassie seemingly confirmed the dating rumors surrounding them by attending several public events together, including at the embattled rap mogul's Paris Fashion Week event and Kanye West's Paris Fashion Week show.

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February 2014: Engagement Rumors Surfaced

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Sean 'Diddy' Combs later deleted the post.

In a since-deleted photo on Instagram, Cassie sparked engagement rumors after she debuted a diamond ring.

"Baby do you like it? I just want to get you wat you Like! I just wanna Mk you smile 🙂 #takeDat!" Diddy captioned the post.

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December 2015: Cassie Ventura Hinted at Their Split

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Sean 'Diddy' Combs and Cassie Ventura seemingly reconciled after their initial split.

In December 2015, the "Long Way 2 Go" songstress uploaded a photo of a sleeping baby meme with the text, "How I sleep … knowing that I'm single and nobody cheating on me." She deleted it afterward.

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August 2016: Sean 'Diddy' Combs and Cassie Ventura Fueled Breakup Rumors

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Model Gina Huynh claimed she began seeing Sean 'Diddy' Combs while he was still dating Cassie Ventura.

TMZ reported Diddy and Cassie had a disagreement in Beverly Hills. At the time, the "Finna Get Loose" rapper reportedly took his then-muse's phone before getting out of the vehicle. He later returned and gave back the phone, said the news outlet.

While it fueled breakup rumors again, Us Weekly squashed the buzz and reiterated they were still together at the time.

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October 2018: Sean 'Diddy' Combs and Cassie Ventura Called It Quits for Good

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Sean 'Diddy' Combs expressed his desire to have more children while he was still dating Cassie Ventura.

A representative for Cassie confirmed the "Miss Your Touch" songstress and Diddy had parted ways for good after being together for over a decade.

"They are indeed no longer together and haven't been for months," a representative for Ventura said at the time.

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November 2023: Cassie Ventura Sued Sean 'Diddy' Combs

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Cassie Ventura accused Sean 'Diddy' Combs of rape and abuse.

Years after the split, Cassie filed a scathing lawsuit against Diddy, accusing him of raping and abusing her over the course of their relationship.

"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," she said in a statement to The New York Times. "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."

Meanwhile, Diddy denied the claims via his legal team, alleging the lawsuit with "baseless and outrageous lies" aimed at "tarnishing [Diddy's] reputation and seeking a payday."

One day after filing the lawsuit, Cassie confirmed she and Diddy reached a settlement. It was later revealed during the hip-hop artist's s-- trafficking trial that Diddy paid her $20 million to settle the case.

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May 2024: CNN Released a Hotel Security Footage That Showed Sean 'Diddy' Combs Assaulting Cassie Ventura

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Cassie Ventura and Alex Fine married in September 2019.

CNN released harrowing hotel surveillance footage from 2016 showing Diddy kicking, hitting and dragging Cassie at the now-closed InterContinental Hotel in Los Angeles, Calif., in 2016.

"The gut-wrenching video has only further confirmed the disturbing and predatory behavior of Mr. Combs," Cassie's legal representative said after the release of the footage. "Words cannot express the courage and fortitude that Ms. Ventura has shown in coming forward to bring this to light."

Diddy, on the other hand, apologized in a video on Instagram, saying his behavior in the clip was "inexcusable."

"I take full responsibility for my actions in that video," he declared, adding, "I was disgusted then when I did it. I'm disgusted now. I went and I sought out professional help. I got into going to therapy, going to rehab. I had to ask God for his mercy and grace. I'm so sorry. But I'm committed to be a better man each and every day. I'm not asking for forgiveness. I'm truly sorry."

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May 2025: Cassie Ventura Took the Stand in Sean 'Diddy' Combs' S-- Trafficking Trial

sean diddy combs cassie ventura relationship timeline
Source: MEGA

Cassie Ventura testified in Sean 'Diddy' Combs s-- trafficking trial.

The entirety of the hotel surveillance footage was shown during Diddy's trial, which began on May 12 in New York City as the disgraced music mogul faces five criminal counts: one count of racketeering conspiracy; two counts of s-- trafficking by force, fraud or coercion; and two counts of transportation to engage in prostitution. Diddy's legal team tried to get the clip excluded from the case, but the court allowed it to be shown during the trial.

Cassie took the stand starting on the second day as she shared further details about their relationship, including the so-called freak offs Diddy organized.

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