Sean 'Diddy' Combs and Cassie Ventura's Relationship Timeline: Everything You Need to Know About Couple's Insane 'Romance'

Sean 'Diddy' Combs' and Cassie Ventura's relationship was filled with violence and dark days.
June 6 2025, Published 9:00 p.m. ET
Sean 'Diddy' Combs and Casandra 'Cassie' Ventura were involved in a wild and violent relationship.
RadarOnline.com can reveal the toxic couple's relationship timeline, concluding with Ventura testifying against Combs.
2005: Combs and Ventura Meet

Combs and Ventura dated for over a decade.
Combs first met 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.
2007: Combs and Ventura Spark Dating Rumors

The pair sparked dating rumors in 2007.
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. Combs is also the father of Justin, Chance, and Love Sean.
Amid the dating rumors, Combs and Ventura maintained their silence over their relationship.
Meanwhile, Porter later confirmed she ended their on-again, off-again romance after 13 years of dating.
2012: Combs and Ventura Seemingly Confirm Their Romance

Combs and Ventura kept a low-key relationship before making public appearances together.
In 2012, Combs and Ventura 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.
February 2014: Engagement Rumors Surface

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," Combs captioned the post.
December 2015: Ventura Hints at Their Split

Combs and 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.
August 2016: Combs and Ventura Fuel Breakup Rumors

Model Gina Huynh claimed she began seeing Combs while he was still dating Ventura.
It was reported that Combs and Ventura disagreed 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, a report squashed the buzz and reiterated they were still together at the time.
October 2018: Combs and Ventura Call It Quits for Good

The two were said to part ways in 2018.
A representative for Ventura 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.
November 2023: Ventura Sues Combs

Ventura spoke out against Combs.
Years after the split, Ventura filed a scathing lawsuit against Combs, accusing him of raping and abusing her throughout 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. "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, Combs denied the claims via his legal team, alleging the lawsuit with "baseless and outrageous lies" aimed at "tarnishing (Combs') reputation and seeking a payday."
One day after filing the lawsuit, Ventura confirmed she and Combs had settled. It was later revealed during the hip-hop artist's sex trafficking trial that Combs paid her $20million to settle the case.

May 2024: CNN Releases a Hotel Security Footage Showing Combs Assaulting Ventura

Hotel footage showed Combs beating Ventura.
CNN released harrowing hotel surveillance footage from 2016 showing Combs kicking, hitting, and dragging Ventura at the now-closed InterContinental Hotel in Los Angeles, California in 2016.
"The gut-wrenching video has only further confirmed the disturbing and predatory behavior of Mr. Combs," Ventura'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."
Combs, 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."
May 2025: Ventura Takes the Stand in Combs' Sex Trafficking Trial

A former girlfriend of Combs has claimed the rapper introduced her to a world of debauchery when they started dating.
The entirety of the hotel surveillance footage was shown during Combs' 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 sex 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.
Ventura took the stand starting on the second day as she shared further details about their relationship, including the so-called freak-offs Combs organized.