Sean ‘Diddy’ Combs and Cassie’s complete relationship timeline


Cassie and Sean “Diddy” Combs dated for more than a decade on-and-off before their split in 2018.

While the “Me & U” singer, 37, and the Ciroc founder, 54, 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.

Combs, for his part, would go on to have romances with City Girls rapper Yung Miami and Dana Tran, whom he welcomed a child with 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.

“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,” Cassie said in a statement via her attorneys at Wigdor LLP.

“Ms. Ventura has now fully escaped Mr. Combs, but the harm that the assaults and sexual abuse he caused her to experience for nearly a decade will forever haunt her,” the filing stated.

Combs has slammed the claims, with his attorney Ben Brafman saying that the rapper “vehemently denies these offensive and outrageous allegations.” He also alleged that Cassie had been demanding $30 million from Combs for the last six months “under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail.”

Cassie alleged that Combs raped and physically abused her in a new lawsuit she filed this month.

Keep reading to see Combs and Ventura’s full relationship timeline.


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.

Cassie (left) and Sean “Diddy” Combs had an on-again-off-again relationship for 11 years.
Matteo Prandoni/


Their relationship was confirmed when they stepped out for Kanye West’s Paris fashion week runway show in March.


She opened up about her rendezvous with Combs in an interview with Madame Noir, calling their love “a completely inspiring experience.”


Engagement rumors swirled when the Bad Boy Records founder posted a snap on Instagram that showed off a big rock on that finger.

Despite not dating until 2007, Cassie and Diddy met in 2005.

However, Combs and the “King of Hearts” crooner never confirmed nor denied a proposal.


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.


In August, police were called after Ventura and Combs had reportedly gotten into an “explosive argument” while driving in Los Angeles.

Cassie and Combs made their first public appearance together in 2012.
Joe Schildhorn/

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.’ ”

The “Step Up 2: The Streets” star (left) and the Bad Boy Records CEO attend a party at Mr Jones on Dec. 31, 2017 in Miami.
Getty Images


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.”

Diddy and Cassie dated on and off for 11 years beginning in 2007.

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.

Cassie and husband Alex Fine married in 2019 and share two daughters together.

Ventura and Fine met through Combs when the latter hired Fine to be her personal trainer.


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.”


Ventura’s Manhattan federal suit was filed with a “trigger warning,” with Ventura claiming 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.

Ventura and Combs.

“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 a dinner. When they got to her residence afterward, he allegedly pushed her inside and raped her.

Ventura has 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.

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