Sean ‘Diddy' Combs and Cassie Ventura: Their complete relationship timeline

Yahoo

15-05-2025

Cassie Ventura endured a tumultuous, decade-long relationship with Sean 'Diddy' Combs before calling it quits in 2018.
After the on-again, off-again couple ended their romance, the 'Me & U' singer moved on with Alex Fine.
Ventura married the personal trainer in 2019, going on to welcome daughters Frankie and Sunny.
Combs, for his part, went on to date City Girls rapper Yung Miami and welcome a baby girl with Dana Tran.
In 2023, Ventura felt 'finally ready to tell [her] story' and filed an explosive lawsuit accusing the record producer of sex trafficking, rape and physical abuse, which he denied.
Take a look back at the exes' time together below.
Combs met Ventura in 2005 when she was 19, one year before the singer's self-titled debut album was released under Bad Boy Records.
The rapper was in an on-again, off-again relationship with Kim Porter at the time, with whom he shared three kids prior to her 2018 death. However, the exes broke up in 2007 after he welcomed a daughter with Sarah Chapman.
That same year, Combs sparked romance rumors with Ventura as the duo were often photographed on red carpets together.
After many outings, the pair seemingly confirmed their romance by sitting side by side at Kanye West's Paris Fashion Week show in 2012.
Ventura claimed in her lawsuit that around this time, she and Combs were actually on a break and he was so 'enraged' by her budding romance with Kid Cudi that he threatened to 'blow up' the 'Day 'n' Nite' rapper's car.
'Around that time, Kid Cudi's car exploded in his driveway,' Cassie's court documents alleged — which Cudi told the New York Times was 'true.'
Ventura and Combs sparked engagement speculation in February 2014 when the Grammy winner posted a picture of a diamond ring that his then-girlfriend was later spotted sporting.
'Baby do you like it?' he captioned the Instagram upload at the time. 'I just want to get you wat [sic] you Like! I just wanna [make] you smile
#takeDat!'
Combs and the model never addressed whether a proposal took place.
In December 2015, Ventura posted — and deleted — an Instagram photo of a resting baby, writing, 'How I sleep … knowing that I'm single and nobody cheating on me.'
Breakup rumors swirled the following summer when a source told Page Six that Ventura 'was acting very much like a single woman' at a party.
TMZ also reported that an 'explosive argument' had taken place between the two in August 2016.
However, the couple subsequently reconciled.
Combs gave a glimpse into his relationship dynamic in a 2016 'Breakfast Club' interview, saying, '25 percent of your time, you're gonna just feel like, 'Aw man, I hate being here, this guy, aw man, he cheated on me, he lied on me.'
'But then there's 75 percent of 'I'ma make you the happiest woman in the whole wide world,'' he continued. ''And I promise you'll smile the most.''
Combs made a rare comment about Ventura on the same radio show in January 2018 while talking about his plans to give Quincy, Justin, Christian, Chance, D'Lila and Jessie a sibling.
'I'm trying to get to 10. It's a race,' he told 'Breakfast Club' listeners. 'Whatever is supposed to happen in the future is going to happen, but that's something that I want.'
The 'Coming Home' rapper clarified, 'I would only have [more kids] with my girl, of course.'
The news of Ventura and Combs' breakup came to light in October 2018, shortly after he was spotted romancing model Jocelyn Chew.
'They are indeed no longer together and haven't been for months,' her rep revealed in a statement at the time.
The duo's last public appearance together was at the May 2018 Met Gala.
Despite Ventura writing 'F–k these hoes' via Instagram after splitting from Combs, she and the songwriter appeared friendly after she announced her engagement and first pregnancy with Fine in 2019.
'Congratulations @Cassie and Alex,' Combs captioned a photo of the couple. 'I wish you all nothing but love and happiness.'
He concluded, 'God bless
L O V E.'
In Ventura's November 2023 court documents, obtained by Page Six, she accused Combs of forcing his way into her home and raping her toward the end of their romance.
She also claimed that Combs made her perform sex acts on male prostitutes while being filmed, also alleging that he had 'frequently beat [her] savagely.'
'She again and again tried to escape his tight hold over her life,' the lawsuit stated. 'Every time she hid, Mr. Combs's vast network of corporations and affiliated entities found her, and those who worked for Mr. Combs's companies implored her to return.'
While Combs' lawyer claimed Ventura had demanded $30 million from the rapper in 'persistent … blatant blackmail,' her attorney said she 'rejected' Combs' alleged offer of 'eight figures to silence her and prevent the filing of this lawsuit.'
In a statement to Page Six, Ventura said, '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.
'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.'
When Combs' Miami and Los Angeles homes were raided by Homeland Security in March 2024, Ventura's attorney reacted.
'We will always support law enforcement when it seeks to prosecute those that have violated the law,' Douglas Wigdor told Page Six in a statement.
'Hopefully, this is the beginning of a process that will hold Mr. Combs responsible for his depraved conduct.'
Combs was arrested in September 2024 on sex-trafficking charges, to which he pleaded not guilty, and held in Brooklyn's Metropolitan Detention Center.
In May 2024, CNN obtained disturbing surveillance footage showing Combs beating, dragging and throwing an object at Ventura at the InterContinental Hotel in Century City, Calif., on March 5, 2016.
Ventura previously detailed the incident in her lawsuit, claiming Combs had become 'extremely intoxicated and punched [her] in the face, giving her a black eye' before she escaped to her apartment.
In response to the 'gut-wrenching video' leaking, Ventura's lawyer, Wigdor, told Page Six that it 'only further confirmed the disturbing and predatory behavior of Mr. Combs,' who did not immediately respond.
Combs' sex-trafficking trial kicked off in New York City in May 2025, and Ventura, who was pregnant with baby No. 3 at the time, was referenced multiple times ahead of her testimony.
Assistant US Attorney Emily Johnson said in her opening statement that a male escort was once forced to urinate in Ventura's mouth while she choked during a 'Freak-Off' party, while witness Daniel Phillip testified that he was paid up to $6,000 to sleep with Ventura as Combs masturbated.
A security guard later spoke about the 2016 hotel beating caught on camera, claiming Combs subsequently threw 'a sack of money' at him with the chilling three-word threat, 'Don't tell anyone.'