Look Back a Diddy and Cassie's Complex Decade-Long Relationship

Sean "Diddy" Combs and his ex-girlfriend Cassie Ventura had a tumultuous relationship before they called it quits for good in 2018. Fans assumed the couple had a loving relationship before their split. However, in the wake of Cassie’s sexual abuse lawsuit against Diddy, it paints a different picture of their romance.

Here's a look back at Diddy and Cassie’s decade-long relationship.

Rumors about Diddy and Cassie's relationship started in 2006 after Diddy signed her to his record label, Bad Boy Entertainment, where she released her first album. Cassie's relationship with Diddy and Bad Boy Record's support helped propel her music career.

In 2007, Diddy appointed her as the spokesmodel for his clothing line, Sean John, sparking more rumors about the two being a pair. At the time, they didn't publicly acknowledge their relationship.

At the time, Cassie was 21 years old and Diddy was 38.

After a long on-and-off relationship with Kim Porter, Diddy officially parted ways with his ex in 2009, cementing Diddy and Cassie's relationship.

Around 2010, it was reported that Diddy paid for Cassie’s apartment, a few minutes drive from where he lived. In addition to covering the apartment expenses, he also bought her a car. In 2012, the duo made their relationship public by attending different events together.

It wasn't until 2013, during an interview with MadameNoire, that Cassie publicly admitted their relationship, terming it "an inspiring experience."

However, in 2013, Diddy denied any plans to marry Cassie, telling The View co-hosts, “It definitely would be a dream come true for me to just one day be ready for that ... I’m not really looking because I know the responsibility that comes with that and I think that a lot of people, they jump into that and they’re not honest with themselves. I’m brutally honest with myself. I don’t want to get married and not make that woman be the best.”

In 2015, the power couple split up briefly and got back together. After reconciling, reports emerged of an altercation between Cassie and Diddy that involved the confiscation and return of her phone. Cassie called her mom, who reported the incident. Law enforcement responded and filed a domestic incident report, but no charges were filed against Diddy. Despite the fight, the couple didn't break up.

Diddy and Cassie's final public appearance was documented on social media in 2018. Cassie's post on Instagram featured them at the Met Gala, while Diddy’s last post celebrated her birthday. In October of that year, Cassie's representative admitted they weren't a couple and hadn't been for months.

A year after splitting up, Cassie began dating her personal trainer, Alex Fine. Today, the couple is married and share two daughters.

In November 2023, five years after their split, Cassie sued her ex-boyfriend Diddy for $30 million, accusing him of rape and physical abuse during their relationship.

They settled just one day after Cassie filed her lawsuit — the amount of the settlement is unknown — but Diddy’s attorney made it clear it was not an admission of guilt.

“Mr. Combs' decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims,” his attorney said in a statement. “He is happy they got to a mutual settlement and wishes Ms. Ventura the best."

Hopefully, Cassie finally got the closure she needed.