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Sean ‘Diddy’ Combs has a lengthy dating history, but he kept some relationships under wraps — including his years-long situationship with actress Cameron Diaz.
Hip-hop mogul Sean ‘Diddy’ Combs has somewhat of a lengthy dating history. The “I Need a Girl” rapper came onto the hip-hop scene in the 1990s, and with the help of his record company, Bad Boy Records, he became one of the most successful stars in the industry.
In September 2024, Diddy was arrested on charges including sec trafficking and racketeering, and he is currently sitting in jail awaiting trial. It’s caused us to go down a rabbit hole regarding Diddy’s dating history, and there is on celebrity that he was linked to, but things didn’t last — what really happened between Diddy and Cameron Diaz?
Did Sean ‘Diddy’ Combs and Cameron Diaz ever date?
Diddy dated a number of high-profile women over the years, and some he was more public with than others. Of course, he had a lengthy relationship with Kim Porter, and he dated Jennifer Lopez for quite a while, too. But Diddy was also linked to Cameron Diaz for some time, though the two never went public with a relationship.
Not much is known about Diddy and Diaz’s relationship, though sources close to the couple said that the two were “on and off” from 2008 to 2012. The timeline is lengthy, given that neither ever truly acknowledged the relationship while it was happening. However, a source close to Diddy said that while out to dinner once, Diddy expressed regret that he didn’t take Diaz more seriously.
“He was at a dinner and the subject turned to Cameron dating Benji Madden,” the source told Us Weekly in 2014. “He said, ‘If I could turn back time, things would be different.’” The source also added that Diddy was “bummed” when he learned that Diaz had started dating Good Charlotte singer Benji Madden, to whom she is now married. However, in true celebrity fashion, things always remained under wraps between Diddy and Diaz, and nobody knows the whole truth.
Many celebrities have distanced themselves from Sean ‘Diddy’ Combs
Combs has received a ton of backlash since his arrest, and rightfully so. Many celebrities have gone to lengths to disassociate from the hip hop mogul, with Ray J even claiming that some celebs attempted to pay off some of Diddy’s victims in an effort to avoid having their names mentioned.
Suge Knight, a former rival of Diddy’s, said that Diddy’s “life is in danger” because of how much he knows about the celebrities who attended his parties. It seems that nobody is certain what’s on camera or what the feds have seen, and Knight seems to think that Diddy should watch his back because some people will go to great lengths to hide things.
