Sean ‘Diddy’ Combs and Cassie: Their complete relationship timeline

Sean “Diddy” Combs and Cassie endured a tumultuous, decade-long relationship before calling it quits in 2018.

After the on-again, off-again couple ended their romance, Cassie moved on with Alex Fine.

The “Me & U” singer married the personal trainer in 2019, going on to welcome daughters Frankie and Sunny.

Diddy, for his part, went on to date City Girls rapper Yung Miami and welcome a baby girl with Dana Tran.

In 2023, Cassie 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.

Back to the beginning

Diddy met Cassie 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 four kids prior to her 2018 death. However, the exes broke up in 2007 after he welcomed a daughter with Sarah Chapman.

That same year, Diddy sparked romance rumors with Cassie as the duo were often photographed on red carpets together.

Laying low

After many outings, the pair seemingly confirmed their romance by sitting side by side at Kanye West’s Paris Fashion Week show in 2012.

Cassie claimed in her lawsuit that around this time, she and Diddy 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.”

Engagement ring rumors

Cassie and Diddy sparked engagement speculation in February 2014 when the Grammy winner posted a picture of a diamond ring Cassie 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!”

Diddy and the model never addressed whether a proposal took place.

Trouble in paradise

In December 2015, Cassie 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 Cassie “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.

Diddy 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.’”

Future family plans

Diddy made a rare comment about Cassie 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.”

It’s over

The news of Cassie and Diddy’s 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.

Amicable exes

Despite Cassie writing “F–k these hoes” via Instagram after splitting from Diddy, she and the songwriter appeared friendly after she announced her engagement and first pregnancy with Fine in 2019.

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“Congratulations @Cassie and Alex,” Diddy captioned a photo of the couple. “I wish you all nothing but love and happiness.”

He concluded, “God bless ❤️❤️❤️ L O V E.”

Going to court

In Cassie’s November 2023 court documents, obtained by Page Six, she accused Diddy of forcing his way into her home and raping her toward the end of their romance.

She also claimed that Diddy 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 Diddy’s lawyer claimed Cassie had demanded $30 million from the rapper in “persistent … blatant blackmail,” her attorney said she “rejected” Diddy’s alleged offer of “eight figures to silence her and prevent the filing of this lawsuit.”

In a statement to Page Six, Cassie 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.”

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