Rapper and business mogul Diddy, formerly known as Puff Daddy, was recently in the news after his former girlfriend and singer, Cassie, filed a lawsuit against him.
According to reports, Diddy consistently abused Cassie since they met in 2005, plying her with drugs, and forcing her to have sex with numerous male prostitutes while he filmed it all.
Per the suit, in the year 2018, as their relationship neared its end, Diddy forced his way into her (Cassie) home and took advantage of her.
However, many people have speculated that the 54-year-old rapper does not treat his women well, and that is why none of them stick around or move from the dating stage to marriage.
This article explores the five women that Diddy has dated in the past:
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Jennifer Lopez
Hollywood actress and renowned singer Jennifer Lopez and Diddy started dating in 1999, although Diddy was still in a relationship with Kim Porter.
In a recent interview with The Breakfast Club, Jennifer Lopez opened up about her relationship with Diddy saying “The Puffy era was just kind of a crazy, heightened time in my life. You know, Puffy and I both grew up in the Bronx.”
“He had been in the music business and had all this success; I was just starting and making my first album when I met him. He became kind of a mentor to me in that moment. We had this kind of crazy, tumultuous relationship that ended in a bang,” she recounted.
They officially broke it off in February 2001.
Kim Porter
Diddy and Kim Porter began dating in the 1990s and had their first child, a boy named Christian Casey, in 1998. In 1999, they ended the relationship and had a legal battle in court over child support for Christian.
Diddy then dated Jennifer Lopez for two years before getting back with Kim Porter in 2003. They welcomed twin girls, D’Lila Star and Jessie James, in December 2006. Unfortunately, Kim Porter sadly passed away from pneumonia in November 2018.
Caresha Brownlee
Caresha Brownlee, 29, and Sean “Diddy” Combs made their affair public in June 2022, but they made it clear that it was not a monogamous relationship.
Caresha Brownlee said she and Diddy, 54, “had our own situation” and refused to label their romance.
“We were f–king with each other hard. We were together every day at one point. He supported me, I supported him. I’ll let the internet call it whatever they want to call it,” she said.
Gina Huynh
In October 2018, rumors circulated that Diddy was dating Gina Huynh. In July 2019, the couple was photographed on a date.
However, Diddy was pictured with his ex Cassie, whom he had split with, in September 2019.
Diddy and Gina’s love life took a turn for the worse. Gina said in a June 2019 interview with Tasha K that Diddy physically mistreated her and paid her $50,000 to terminate her pregnancy not once, but twice.
Cassie Ventura
Diddy and Cassie had an on-and-off relationship for over 10 years. They began dating secretly in 2007, and their relationship was formally recognized in 2012.
Throughout 2015 until 2018, the pair was rumored to have broken up and gotten back together a number of times.
However, the pair officially split for the last time in October 2018, following reports that Diddy was hesitant about settling down with Cassie.
Cassie recently filed a lawsuit in 2023, which depicted Combs as an erratic, controlling individual with violent tendencies aimed at her and others. She also disclosed that Diddy forced her to have sex with numerous male prostitutes while he filmed it.
Later, reports went viral that Diddy had settled their issues out of court.