- Cassie Ventura is an American singer, Diddy is an American rapper
- Ventura is currently testifying against him in his sexual assault trial in New York
- The exes dated from 2007 until 2018 and had a volatile relationship
Singer Cassie Ventura, 38, is currently testifying against her ex, Diddy, 55, real name Sean Combs, in his highly publicized sexual assault trial in New York. Cassie and Diddy dated from 2007 until 2018.
Back in November 2023, Cassie filed a lawsuit against her ex, accusing him of sexual and physical abuse. After his mansion was raided in 2024, Diddy was charged with racketeering, sex trafficking, and transportation to engage in prostitution. He has pleaded not guilty.
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Now, Cassie has bravely taken the stand in the trial, which is now on day three. Here she alleges Diddy made her take part in multiple day-long sex parties with escorts, known as ‘freak offs’. She alleges he was also abusive during this time and would film and direct the freak-off videos.
Let’s take a look back at their decade-long relationship, before the allegations surfaced.
Cassie and Diddy: A decade-long relationship
Back in 2005, Cassie released her debut single Me & You. Instantly, the song became a club hit, which led her to Diddy. Reportedly, he heard her song in a nightclub.
Cassie and Diddy first met when she was 19 years old, and he was 37.
From there, Diddy started to work with Cassie on her self-titled debut album under his label, Bad Boy Records. This year, Diddy and his long-term ex and the mother to three of his children, Kim Porter, split up for good.
Subsesquently, he began dating Cassie. Their romance continued for years in a low-key manner.
2012 – first public appearance
However, Cassie and Diddy remained tight-lipped about their romance until they made their couple debut at Kanye West’s Paris Fashion Week show in 2012. There was more to the story at this time, as Cassie alleges she and the Bad Boy Records founder were on a break then.
Two years later, more rumors surfaced, this time, engagement rumors. Diddy boasted by posting a picture on Instagram of a ring his girlfriend was wearing.
However, nothing ever came of the rumors, as the two did not address any engagement.
2015 breakup?
By this time, multiple rumors swirled about a breakup between the two. One model came forward and claimed she was seeing Diddy. Meanwhile, in late 2015, Cassie fuelled the rumors by posting a meme on Instagram, acknowledging her being single.
Additionally, sources told Page Six in the summer of 2016 that Cassie was flirting with someone other than the I’ll Be Missing You singer. Also, that summer in August, a report by TMZ said the two had gotten into a heated argument in a car.
Apparently, the Me & You singer told the rapper she wanted to break up.
Then Diddy allegedly grabbed her phone and jumped out of the car. Following that, the police were called as Cassie had told her mom of the incident. A domestic incident report was written, but no charges were filed.
That next month, the two were papped at an event honoring Diddy, so they reconciled very quickly.
In an interview with The Breakfast Club, Diddy gave a slight glimpse into their volatile relationship in 2016. Indirectly, he acknowledged lying and cheating, which could reference his dynamic with Cassie.
On the same show a year later in January 2018, Coombs spoke about having more children with “[his girl], referencing Cassie.
The two never had children.
October 2018 – the last breakup of Cassie and Diddy
Finally, in October 2018, Cassie and Diddy broke up for the last time. “They are indeed no longer together and haven’t been for months,” Cassie’s rep confirmed to Love B. Scott.
As for their last public appearance, that was in May 2018.
By late 2018, Cassie had launched her relationship with Alex Fine. He is now her husband, with whom she will soon have three kids.
Strangely, Diddy congratulated his ex when she moved on on social media.
2023 – Lawsuit
Five years post-breakup, Cassie filed a lawsuit in November 2023. She accused Diddy of raping her towards the end of their relationship, beating her, and making her engage with male prostitutes (which later became known as the freak offs).
Despite settling out of court, in May 2024, surveillance video footage leaked of Diddy attacking Cassie at the InterContinental Hotel in Century City in March 2016.
A few months later, Diddy was arrested and charged in September 2024, although not related to Cassie specifically.
In May 2025, Cassie at eight months pregnant, testified against her ex-boyfriend, alleging details from their relationship and what she went through for 10 years.
