Sean Combs, known by his stage name “Diddy” (or Puffy, P. Diddy, Puff Daddy, and Love, depending what year you asked him), has quite the track record of celebrity relationships.
Diddy’s dating history, which includes Jennifer Lopez and Naomi Campbell, is a list that’s pretty long. But a fling he had going into the 2010s is the only one he’s ever seemed reminiscent of, and that is of his relationship with actress Cameron Diaz.
The two initially hooked up in 2008 and were somewhat together for four years, eventually ending things in 2012. By 2014, Diaz had started dating Benji Madden, the lead guitarist of the pop punk band Good Charlotte.
The news of them dating, at the time, made Diddy miss the years they spent together.
“He was at a dinner and the subject turned to Cameron dating Benji Madden,” a source told Us Weekly in 2014. “He said, ‘If I could turn back time, things would be different!’”
“He was bummed,” the source added, “saying, ‘She’s the sexiest girl in the world.’”
When Diaz and Combs were together, they were notorious for repeatedly engaging in PDA. Most notably, in 2012, Diaz was spotted “straddling” Combs at a party in West Hollywood.
An eyewitness told Us Weekly at the time, “Her hair was all crazy, her makeup was smeared and they made out in front of everyone. She was acting like a teenager!”
Since their split, Diaz ended up marrying Madden in 2015 and the two have welcomed their only child together, Raddix.
In 2020, she went on Instagram Live and talked about her experience being a parent alongside Benji.
“I love being a mother. It’s the best, best, best part of my life,” she said at the time. “I’m so, so grateful and so happy and it’s the best thing ever and I’m so lucky to get to do it with Benji and we’re just having the best time. It’s so great. I’m just thrilled.”
As for Diddy, he has had a few on-and-off flings in the years since his and Diaz’s split, including with model Lori Harvey and singer Cassie Ventura. Most recently, though, Diddy has been involved with rapper Yung Miami.
Drama ensued among fans late last year when Diddy welcomed his sixth child, daughter Love, and it was clarified that Yung Miami is not mother, despite having been with each other for six months at the time.
As of now, they seem to still be in a relationship, having spent New Year’s together.