SUMMARY
  • Cameron Diaz and P. Diddy Combs hooked up after her split from Alex Rodriguez.
  • Sean Diddy Combs regretted their relationship ending.
  • New details about Freak Offs were recently shared by a party planner.

Sean Diddy Combs, or P. Diddy, is one name that has been circling the entertainment world for a while now. The Grammy-winning record producer is credited with the discovery and development of the musical career of artists including Usher, Mary J. Blige, and more. He is one of the wealthiest and most influential musical artists in the industry. However, things haven’t been in Diddy’s favor since his former partner Cassie Ventura went ahead to file a multimillion-dollar s**ual assault lawsuit against him.

Diddy
Sean Diddy Combs at Ellen DeGeneres Show | Credits: Ellen DeGeneres’ YouTube

The two of them settled the case outside court the very next day, but what followed was a sea of lawsuits that alleged that Combs had s**ually abused multiple individuals between 1991 and 2009. The record producer was arrested in September and is now awaiting trial at the Metropolitan Detention Center in Brooklyn. The high-profile case has led to fans digging up Diddy’s past, which includes his hot and heavy affair with Cameron Diaz.

Cameron Diaz and Sean Diddy Combs reportedly ‘couldn’t help themselves in public’

Actress Cameron Diaz dated Alex Rodriguez in 2010, but the duo decided to focus on their careers and went their separate ways in 2011. It was reported that dear friend Gwyneth Paltrow was trying to play a matchmaker between Diaz and British star Jude Law, but P. Diddy ended up in the picture with Diaz instead. The duo first met at the Academy Awards 2008, and spent the whole evening together, laughing and flirting.

The Things noted that Diaz’s hooking up with P. Diddy helped her to get over her romance with Rodriguez. The two of them were caught making out numerous times but denied their relationship being anything other than platonic. The record producer at the time stated that a man and a woman can perfectly be just friends. But according to Life & Style magazine (via Glamour),

They were making out like teenagers.

It was reported that the sparks between Diaz and Diddy were so strong that they couldn’t even help themselves in public. Multiple eyewitnesses shared with US Weekly the time that they caught the duo making out in front of everyone at Soho House in West Hollywood. They said,

Her hair was all crazy, her makeup was smeared, and they made out in front of everyone. She was acting like a teenager.

Diddy was linked to Cameron Diaz
Cameron Diaz reportedly hooked up with P. Diddy following her split from Alex Rodriguez | Credits: Kevin Hart’s YouTube

Cameron Diaz’s representative denied all the claims. After things turned bitter between Diaz and Diddy, they went their separate ways, and it’s something Diddy regrets. A source shared with US Weekly,

He was at a dinner, and the subject turned to Cameron dating Benji Madden. He said, ‘If I could turn back time, things would be different’. He was bummed, saying, ‘She’s the sexiest girl in the world.’

The actress finally met Benji Madden at an event in May 2014, and the two of them started dating, and by 2015 they were married. They share two kids, Raddix Madden and Cardinal Madden. Diaz shared about her successful marriage during her appearance on Michelle Visage’s Rule Breakers podcast, stating that he’s taught her to value herself a lot more. Cameron Diaz added that their marriage is the most valuable thing she has.

With Diddy’s arrest last month and a lot of his past being dug out, which is nothing but extremely disturbing and shocking, his affair with Diaz also became a part of it just like his affair with Jennifer Lopez. But fans do wonder if the actress now regrets hooking up with the record producer. 

Party planner shares P. Diddy’s extremely particular about women attending his Freak Offs

In new details about Sean Diddy Combs’ case, one party planner who worked with Diddy in 2004 and 2005 spoke to the NY Post. She noted that Diddy was very particular about the women attending his alleged ‘Freak Off’ s*x parties. The party planner said,

We would do a weigh-in if necessary. The girls had to be young and hot, so I always had a scale nearby in case I needed to make sure. The number was 140 pounds, but if the girl was tall, there was a little bit of discretion involved. No flab, no cellulite, not overly pierced or tattooed. No short hair. And the girls had to be young and hot.

Diddy Combs
Sean Diddy Combs in an interview with Vogue| Credits: Vogue’s YouTube

The party planner said to the publication that the record producer had a strict dress code where girls had to wear dresses, preferably very short, just enough to cover their butt cheeks. They insisted on wearing stilettos. She added that they never asked the girls about their age, and she assumed that they weren’t asking because of drinking laws.

She, however, clarified that she never stayed around for the Freak Offs and had no idea that the girls were expected to have s*x with people who attended the parties. A dancer who performed at Combs’ 2005 VMA afterparty was allegedly paid $250 for the event but was told that an extra $1000 would be given if she went to P. Diddy’s house. She didn’t go.

The Post noted that Freak Offs wasn’t always consensual, and to ensure participation, Combs used violence and intimidation and leveraged his power over victims. He was arrested on the charges of s*x trafficking, racketeering, and transportation to engage in pr*stitution. Diddy has denied all the allegations and is awaiting his trial, which is scheduled for May 5, 2025.

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