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Sean “Diddy” Combs and Cassie’s relationship was tumultuous and a focal point of the hip-hop mogul’s scandal. The pair dated for years, ending with an out-of-court settlement after Cassie accused Diddy of abuse, violence, and sex trafficking.

The relationship, which ended in 2018, went back under the microscope following Combs’ September 2024 arrest on charges related to racketeering, sex trafficking by force, and transportation for purposes of prostitution. While other celebrities raised red flags about Combs, his hypocrisy toward Cassie provides an unsettling look at his behavior.

Cassie raised questions after Diddy reunited with ex Jennifer Lopez

Sean “Diddy” Combs and Jennifer Lopez broke up in 2001 after a relationship that had its share of controversy and scandal. But the two remained relatively close, even after Lopez married and Diddy began dating Cassie.

Cassie’s 2023 lawsuit claimed Diddy raped and abused her when she tried to leave the relationship. However, Diddy appeared to have a different perspective on fidelity in his comments about reuniting with Lopez at the 2015 American Music Awards.

In Diddy’s interview with The Breakfast Club, he claimed Cassie didn’t have a problem with his being friendly toward an ex. But at the same time, he suggested Cassie wasn’t initially thrilled.

“She had some questions,” Diddy said. “She had some questions but not, not…you know, Casper [Smart, Lopez’s boyfriend] was there. Me and Jennifer, people gonna be friends, man, people gonna grow, and, any of my exes, they smile and they’re happy to see me, and that’s all that was about. And, you know, I answered the question and we kept it moving.”

Diddy’s claim that any of his ex-girlfriends are happy to see me certainly didn’t apply to Casandra Ventura.

Diddy had approval over Cassie’s love scenes in a movie

Cassie’s career extended beyond music. She also has a handful of acting credits on her resume, including the 2016 romantic comedy The Perfect Match.

Cassie’s co-star Terrance J reached out to Diddy prior to filming. The actor wanted to get the hip-hop mogul’s approval regarding love scenes with Cassie.

In a 2016 interview with The Breakfast Club, Diddy claimed he wanted Cassie’s love scenes to feel as real as possible. “I wanted him to know that it’s a movie, man, go do your thing. I respect the art,” he said.

But Diddy changed his tune later in the interview, sharing that he wasn’t always comfortable watching Cassie’s performance. “I was a little bit sick. I was watching the movie and I’m like, ‘This is the third love scene.’ I’m tapping her, I’m like, ‘Yo, you really in the movie.’ 

“They had a little screening for me, Terrence had a little screening for me. Because they were like, ‘Puff, we want to make sure that everything’s cool.’ So, I’m looking at her like, ‘Yo, you getting smashed three times in the joint and you ain’t even say nothing.’ I’m like, ‘Where the arc in your character?’ And she’s just like, ignoring me.”

Considering Diddy once admitted that his partners should expect him to cheat and lie “25% of the time,” it’s hypocritical for him to get defensive over a movie.

Diddy’s apology after leaked video showed him abusing Cassie didn’t seem sincere

@showbizcheatsheet

A body language expert weighs in on Diddy’s apology.

♬ original sound – Showbizcheatsheet

Sean “Diddy” Combs’ attorney denied Cassie’s allegations of domestic violence outlined in her 2023 lawsuit. But a leaked video proved there was some truth to Cassie’s claims.

The 2016 video shows Diddy physically assaulting Cassie in a hotel. It came just a year before Diddy rebranded himself as “Love,” a hypocrisy not lost on anyone who saw the leaked footage.

Diddy’s 2024 apology video was met with skepticism and criticism. One source claimed Diddy believes the video didn’t tell the whole story. A body language expert told Showbiz Cheat Sheet the apology sounded too rehearsed and lacked authenticity. 

How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area. 

How to get help: In the U.S., call the National Domestic Violence Hotline at 1-800-799-7233 or text START to 88788.