Sean ‘Diddy’ Combs and Cassie’s complete relationship timeline
Cassie and Sean “Diddy” Combs dated for more than a decade on-and-off before they split in 2018.
While the “Me & U” singer, 38, and the Ciroc founder, 55, had many ups and downs over the years, they both found other partners following their breakup.
Cassie, whose birth name is Casandra Ventura, tied the knot with fitness trainer Alex Fine in late 2019 after meeting a year prior. The pair are now parents of young daughters Sunny and Frankie, with a third on the way.
Combs, for his part, would go on to have romances with City Girls rapper Yung Miami and Dana Tran, with whom he welcomed a child in 2022.
One year later, New York City native Combs was sued by Cassie in November 2023, accusing him in a bombshell lawsuit of trafficking, rape and physical abuse.
Although they settled the stunning lawsuit almost as quickly as it was filed, Diddy’s world came tumbling down the next year when his homes were raided and, months later, he was arrested for a slew of federal charges.
Ventura was one of the first witnesses to take the stand when his trial kicked off in Manhattan in May 2025.
Keep reading to see Combs and Ventura’s full relationship timeline.
2007
The former couple first locked eyes in 2005 and began dating two years later. The rapper had just broken up with late ex Kim Porter at the time.
Ventura was hired for Combs’ clothing line Sean John and was signed to his label, Bad Boy Records, in 2007.
2012
Their relationship was confirmed when they stepped out for Kanye West’s Paris fashion week runway show in March.
2013
She opened up about her rendezvous with Combs in an interview with Madame Noir, calling their love “a completely inspiring experience.”
2014
Engagement rumors swirled when the Bad Boy Records founder posted a snap on Instagram that showed off a big rock on that finger.
However, Combs and the “King of Hearts” crooner never confirmed nor denied a proposal.
2015
Fans wondered if the duo parted ways after Ventura shared a meme of a baby snoozing on social media. “How I sleep … knowing that I’m single and nobody cheating on me,” she captioned the post.
But she soon deleted the photo shortly after posting.
A source told Page Six at the time that she “was acting very much like a single woman” at a bash.
2016
In August, police were called after Ventura and Combs had reportedly gotten into an “explosive argument” while driving in Los Angeles.
Sources told TMZ at the time that Ventura wanted to break up with him, and the idea caused him to grab her phone and erratically jump out of the car with it.
Later that year, they appeared to reconcile and Combs appeared on the radio program “The Breakfast Club.”
“Twenty-five 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,’ ” he said.
“But then there’s 75% of, ‘I’ma make you the happiest woman in the whole wide world,’ ” he said. “ ‘And I promise you’ll smile the most.’ ”
2018
In January, the “Get Him to the Greek” actor stopped by the Power 105.1 station’s show again and revealed that he wanted to expand his brood with Ventura.
He was already a father to children King, Quincy, Justin, Christian, Chance, D’Lila and Jessie.
“I’m trying to get to 10. It’s a race,” he explained. “Whatever is supposed to happen in the future is going to happen, but that’s something that I want. I would only have [more kids] with my girl, of course.”
By the time October rolled around, the songwriter and rapper, formerly known as Puff Daddy, officially broke up.
“They are indeed no longer together and haven’t been for months,” Ventura’s rep said in a statement at the time.
That December, she announced she was dating Fine, now 30, with a cute social media kissing post.
Ventura and Fine met through Combs when the latter hired Fine to be her personal trainer.
2019
When Fine and Ventura announced their engagement in August, things seemed friendly between her and the Diddy – Dirty Money member.
Combs congratulated the pair on their happy news, writing on social media: “Congratulations @Cassie and Alex. I wish you all nothing but love and happiness. God bless ❤️❤️❤️ L O V E.”
2023
Ventura’s Manhattan federal suit was filed with a “trigger warning” in New York federal court on Nov. 16. Ventura claimed that Combs abused her between 2005 through 2018 during their on-and-off relationship.
Some of her claims included that Combs allegedly “savagely” and “frequently” beat her multiple times over the years. In January 2009, she alleged that Combs became “enraged” when he witnessed her speaking with another music manager at an LA party. He then allegedly pushed her out of the club and into a car, where he stomped on her face until she was covered in blood.
Ventura also alleged that in 2012, Combs threatened to blow up rapper Kid Cudi’s vehicle when he learned that she and Cudi dated when she wasn’t with Combs at the time.
“In February 2012… Mr. Combs told Ms. Ventura that he was going to blow up Kid Cudi’s car and that he wanted to ensure that Kid Cudi was home with his friends when it happened,” read court documents obtained by The Post. “Around that time, Kid Cudi’s car exploded in his driveway.”
Through a spokeswoman, Kid Cudi confirmed Ventura’s account to the New York Times. “This is all true,” he said.
Years later in 2018, Venura claimed that she broke up with Combs over dinner. When they got to her residence afterward, he allegedly pushed her inside and raped her.
Ventura received support from many amid her allegations, including members of Danity Kane (which Combs formed through MTV’s “Making the Band” in 2005) and her husband, Fine.
Combs quickly settled the lawsuit with Ventura one day later on Nov. 17. However, details surrounding the agreement were not revealed.
Following the “Me & U” singer’s lawsuit, more than two dozen alleged victims also came forward with similar claims against the embattled record producer.
2024
On Mar. 25, 2024, Diddy’s homes in Los Angeles and Miami were raided by federal agents with Homeland Security Investigations and other law enforcement officials.
The searches were part of an investigation launched by federal authorities in New York.
On May 17, CNN released a shocking surveillance video from 2016 of Diddy assaulting Ventura in the hallway of the InterContinental Hotel in Century City, Calif.
“I hit rock bottom – but I make no excuses,” Diddy said in an apology video after the footage was released. “My behavior on that video is inexcusable. I take full responsibility for my actions in that video.”
Ventura’s lawyers quickly responded to the rapper’s apology, saying, “Combs’ most recent statement is more about himself than the many people he has hurt.”
The “Long Way 2 Go” singer also released a statement.
“Domestic Violence is THE issue,” she wrote on Instagram at the time. “It broke me down to someone I never thought I would become. With a lot of hard work, I am better today, but I will always be recovering from my past.”
Four months later, on Sept. 16, Diddy was arrested at the Park Hyatt Hotel in Manhattan and charged with racketeering, sex trafficking, and transportation to engage in prostitution.
An indictment unsealed one day later accused Diddy of creating a “criminal enterprise” whose members both engaged in and attempted to engage in sex trafficking, forced labor, kidnapping, arson, bribery and obstruction of justice.
He pleaded not guilty and denied all the allegations against him. The rapper was held at the Metropolitan Detention Center in Brooklyn, where he remained as his trial kicked off.
2025
Diddy’s federal trial officially started with jury selection in a Manhattan courtroom on May 5.
Ventura, who is took the stand on May 13.
She testified about the early stages of the pair’s relationship, her allegations of abuse and Diddy’s alleged interest in watching her “be in intercourse” with another man.
Ventura also testified about Diddy’s purported “Freak Offs” and the altercation caught on surveillance video at the InterContinental hotel in 2016.
Douglas Wigdor, Ventura’s attorney, said that he was “super proud” of the singer as they left the NYC courthouse on May 13.
“It was a long day,” he said, per CNN. “I’m just super proud of her.”
Ventura is set to return to the witness stand on Wednesday, May 14, to continue her testimony and be cross-examined by Diddy’s defense attorney, Anna Estevao.