Sean “Diddy” Combs and Cassie, his ex-girlfriend, navigated a tumultuous romance before officially parting ways in 2018. Despite Cassie’s subsequent marriage to Alex Fine and the birth of her child, the saga with Diddy continues to make headlines. In November 2023, The New York Times reported Cassie filing a lawsuit against Diddy, alleging a history of abuse during their time together over ten years.
According to court documents obtained by WMV, Cassie claimed that Diddy coerced her into drug use, physically assaulted her, and compelled her into sexual encounters with male sex workers while recording them. She further accused Diddy of forcibly entering her home and raping her in 2018. Diddy vehemently denied these allegations, deeming them “offensive and outrageous.”
WMV takes a closer look at the key moments in Diddy and Cassie’s relationship:
2007: The couple first met in 2005 and became romantically involved two years later. Casie was formerly with singer Ryan Leslie who introduced her to Diddy. After they broke up Ryan stated, “I love Cassie. I fell in love with her, I fell in love with the music, I fell in love with her family.”
2012: Cassie and Diddy publicly confirmed their relationship by attending various events together, including Kanye West’s Paris Fashion Week runway show.
2013: In an interview with Madame Noir, Cassie describes her relationship with Diddy as inspiring, “just being around him is a completely inspiring experience.” She also mentioned how honesty “and communication were huge factors in their romance.”
February 2014: Engagement rumors sparked when Diddy posted an Instagram photo of a diamond ring with a caption expressing affection. Although Cassie was later seen wearing the ring, neither party confirmed an engagement.
December 2015: Rumors of a breakup circulated after Cassie posted a suggestive meme on Instagram. However, the post was quickly deleted. They did an interview with The Breakfast Club, where Diddy shared his 25/75 relationship rule. “If I’m in a relationship with you, like 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,’” Diddy said. “But then there’s 75 percent of ‘I’mma make you the happiest woman in the whole wide world,’ and I promise you’ll smile the most.”
August 2016: Following a TMZ publicized argument in Beverly Hills, breakup rumors surfaced. Nevertheless, it was confirmed that Cassie and Diddy were still together, with the altercation being characterized as a mere argument.
January 2018: Diddy expressed his desire for more children during a radio appearance, stating he wanted to have them with Cassie. They attended the Met Gala in May and she posted the event, while Diddy posted on her birthday in August, captioning “Go BEST FRIEND ! ITS YOUR BIRTHDAY — HAPPY BIRTHDAY to MY LOVE ?? @cassie LOVE YOU 4eva #CassieDay”.
October 2018: It was announced that Cassie and Diddy had permanently parted ways. The split coincided with Diddy being seen with model Jocelyn Chew in Miami.
January 2019: Cassie moved on with personal trainer Alex Fine, causing a reported blow to Diddy’s ego. The insider claimed it was their most significant breakup after a decade of on-and-off romance.
June 2019: Diddy congratulated Cassie and Alex Fine on their pregnancy via social media, expressing his well-wishes.
September 2019: After news of Cassie and Fine’s wedding, Diddy shared a cryptic message on Instagram. Cassie later welcomed their first daughter, Frankie, and expanded their family in March 2021 with the birth of daughter Sunny.
November 2023: Cassie filed a lawsuit against Diddy, alleging abuse and assault. Diddy denied the claims, and a settlement was reached the following day, ending the legal dispute. Cassie expressed her desire for an amicable resolution, thanking her family, fans, and lawyers for their support. Diddy echoed the sentiment, stating they had decided to resolve the matter amicably.
