Sean ‘Diddy’ Combs and Cassie: Relationship Timeline

Diddy and Cassie at dinner
Diddy and Cassie at dinner

Cassie and Sean “Diddy” Combs were in an on-and-off relationship for over a decade before parting ways in 2018.

Despite the ups and downs in their relationship over the years, the 37-year-old “Me & U” singer and the 54-year-old Ciroc founder eventually went their separate ways in 2018. Both of them found new partners after their breakup.

Cassie (real name Casandra Ventura), married fitness trainer Alex Fine in late 2019, a year after they first met. The couple is now happily parenting their young daughters, Sunny and Frankie.

On the other hand, Combs went on to have relationships with City Girls rapper Yung Miami and Dana Tran. He welcomed a child with Dana Tran in 2022.

One year later, in November 2023, New York City native Combs faced a lawsuit filed by Cassie, alleging him in a bombshell legal action of trafficking, rape, and physical abuse.

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

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

The filing stated, “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.”

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

Continue reading to explore the complete timeline of Combs and Ventura’s relationship.

2007

The couple first met in 2005 and started dating two years later. At that time, the rapper had recently ended a relationship with his late ex, Kim Porter. Ventura got involved in both Combs’ work and personal life, initially hired for his clothing line, Sean John, and later signed to his record label, Bad Boy Records, in 2007. Their connection grew as they navigated both work and romance, shaping their relationship during Ventura’s time at Sean John and Bad Boy Records.

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

2012

Their relationship was officially confirmed when they made a public appearance at Kanye West’s Paris Fashion Week runway show in March.

2013

She shared details about her relationship with Combs in an interview with Madame Noir, describing their love as “a completely inspiring experience.”

2014

Engagement rumors started swirling when the founder of Bad Boy Records posted a picture on Instagram that showed off a big rock on that finger.

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

However, Combs and Cassie never confirmed nor denied a proposal.

2015

Fans began speculating about a possible breakup when Ventura posted a meme on social media featuring a baby sleeping, with the caption, “How I sleep … knowing that I’m single and nobody cheating on me.” However, she quickly deleted the post after sharing it. Around the same time, a source informed Page Six that she “was acting very much like a single woman” at a social event.

2016

In August, police were called following reports of an “explosive argument” between Ventura and Combs while they were driving in Los Angeles.

Sources informed 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.

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

Later that year, it seemed they had reconciled, and Combs made an appearance 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.’ ”

Cassie Diddy
Cassie and the Bad Boy Records CEO attend a party at Mr Jones on Dec. 31, 2017 in Miami.

2018

In January, Diddy stopped by the Power 105.1 station’s show again and revealed that he wanted to expand his family with Cassie.

At that time, he was already a father to children named 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 Cassie
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 ended their relationship.

“They are indeed no longer together and haven’t been for months,” Ventura’s representative stated in a statement at the time.

That December, she announced she was dating Fine, now 30, with social media post featuring a kiss.

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

Ventura and Fine met through Combs when the latter introduced Fine as her personal trainer.

2019

When Fine and Ventura announced their engagement in August, the relationship between her and the Diddy seemed friendly.

Combs congratulated the pair on their happy news, expressing 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 lawsuit, filed in Manhattan federal court, came with a “trigger warning,” alleging that Combs had abused her from 2005 through 2018 throughout their on-and-off relationship.

Some of her claims included allegations that Combs allegedly “savagely” and “frequently” beat her on multiple occasions over the years. In January 2009, she claimed that Combs became “enraged” when he saw her talking to another music manager at a party in LA. According to her, he then pushed her out of the club and into a car, where he allegedly 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 found out that she and Cudi had dated during a period when she wasn’t with Combs.

Ventura and Combs
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. “Around that time, Kid Cudi’s car exploded in his driveway.”

Kid Cudi confirmed Ventura’s account through a spokeswoman, stating to the New York Times, “This is all true,” he said.

Years later, in 2018, Ventura claimed that she ended her relationship with Combs over dinner. Afterward, when they arrived at her residence, he allegedly pushed her inside and raped her.

Ventura has garnered support from numerous individuals amidst her allegations, including members of Danity Kane (which Combs formed through MTV’s “Making the Band” in 2005) and her husband, Fine.