Trigger Warning: This article discusses alleged sexual assault and sex trafficking.
Throughout Sean ‘Diddy’ Combs’ career in the public eye as a rapper, record producer, and record executive starting in the 1990s, he’s had a slew of high-profile girlfriends.
Most notably, R&B singer Cassie Ventura, whose lawsuit against Combs opened up a pathway for other brave women to come forward and assist with the federal indictment case currently awaiting trial.
As the rap mogul’s arrest in New York over charges relating to sex trafficking, racketeering, and transportation to engage in prostitution, draws renewed focus on everyone in his orbit, including the artists he mentored, the women he dated and had children with, we take a look back at his past relationships, from the early nineties, until now.
Sean ‘Diddy’ Combs’ Relationship With Misa Hylton
Diddy – then known as ‘Puff’ or ‘Puff Daddy’, started dating fashion designer Misa Hylton in the early nineties, after she began working with him as he rose through the ranks at Uptown Records.
In a 2023 interview with BET, Hylton spoke about working with Combs on the styling for music group, Jodeci, after which her own career really kicked off.
In December of 1993, the pair welcomed their first – and only – child, Justin, only to break up shortly after.
While the couple’s relationship was short-lived, they have seemingly maintained a close co-parenting arrangement, confirmed when Hylton was photographed at Diddy’s 50th Birthday party.
Diddy’s Relationship With Kim Porter
In 1994, not long after Combs and Hylton parted ways, he would begin his near decade-long on-again, off-again relationship with model, Kim Porter.
“The first time I saw her, she was at the studio with her ex-boyfriend,” Sean ‘Diddy’ Combs shared in an interview with Essence. The rapper was referring to Kim’s ex -boyfriend, singer AI B. Sure, the father of Kim’s child Quincy.
“She kind of made me nervous,” Combs continued. “She wasn’t like a New York girl. She was Bohemian, mixed with Georgia-peach hospitality. I got the idea she’d like doing stuff like walking barefoot in the grass. I didn’t think I could get her to like me. She was smooth, you know, like ice. She’s cool and collected and thinks before she speaks. You meet a lot of young ladies, and they just don’t do that. Kim was never pressed; she was always in control.”
The tumultuous relationship was not without its flaws. After welcoming Christian “King” Combs, their first child together in 1998, the couple ended things just a year later in 1999, when Diddy began dating actress and singer, Jennifer Lopez.
After the breakdown of Lopez and Combs’ relationship, Kim and Diddy rekindled theirs, getting back together in 2003 and welcoming twin daughters D’Lila Star and Jessie James Combs in 2006.
The one-year-after-kids pattern seemed to rear its ugly head again, as the couple parted ways for the final time in 2007.
It was revealed later, that Kim had found out about Diddy fathering a child with friend, Sarah Chapman, the same year she gave birth to their twins.
The ex-partners remained on good terms right up until Porter tragically passed away in November 2018 at age 47.
Sean ‘Diddy’ Combs’ Relationship With Jennifer Lopez
The year was 1999 and J. Lo’s debut album On The ^6 produced by Combs, had just been released, earning Lopez her well-deserved A-list status.
But while they may have started work as colleagues, their relationship soon turned romantic, with the pair announcing their relationship in 1999.
During this time, J. Lo’s star was rising at a rapid speed, with a global hit record and of course, that green Versace dress, catapulting her into the pop culture stratosphere. But that same year, the couple were involved in a disagreement at a Manhattan club in which shots were fired resulting in three people being injured.
While Combs and Lopez were both arrested after leading police on a chase through New York City before a stolen gun was found inside their car, charges against Lopez were quickly dropped.
Combs, however, was forced to stand trial for gun possession and alleged bribery, before being acquitted.
Despite the scandal, J. Lo and Combs stayed together until 2001.
Two years after the pair broke things off, Lopez spoke with Vibe magazine about Diddy’s infidelity. “It was the first time I was with someone who wasn’t faithful.” ”I never caught him, she continued, “but I just knew. … I had to think, ‘Do I want to be home with kids in 10 years wondering where somebody is at three in the morning?’”
Did Diddy Date Cameron Diaz?
Though neither Diddy or Cameron Diaz ever confirmed either way, the pair were surrounded by dating rumours briefly in 2008.
Cassie and Diddy’s Relationship
R&B singer, whose real name is Cassandra Ventura, was first linked to Sean ‘Diddy’ Combs in 2007 shortly after he and ex-girlfriend Kim Porter had split for the final time, but didn’t go public with their relationship until 2012.
However, Cassie was first introduced to Combs in 2005, when he began work producing the then-teenager’s first album.
According to a lawsuit filed against Combs in the Federal District Court in Manhattan, on Thursday 16 November, 2023, Cassie claimed that Combs began abusing her soon after that initial meeting in 2005, up until Cassie was able to finally end the relationship in 2018.
“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,” Ventura said in a statement at the time of filing, per The New York Times.
While Sean ‘Diddy’ Combs denied the allegations filed against him in November 2023, the complaint obtained and shared by PEOPLE, stated that: “All aspects of Ms. Ventura’s life were controlled by either Mr. Combs or his management companies.”
Sean ‘Diddy’ Combs and ex-girlfriend Cassie reached a legal settlement before the case made its way to court, but her brave testimony set in motion the events we’re seeing play out today.
Lori Harvey Linked To Diddy
Sean Combs, 49, and then-22-year-old Lori Harvey sparked dating rumours in July 2019, after they were spotted by photographers walking together through New York City’s SoHo.
Shortly after their initial link, the pair were snapped holidaying with Lori’s mum and stepdad, Steve Harvey, in Nerano, Italy.
Since then, Diddy has been linked to various other women, but has maintained his single status.
