There was a time when Sean “Diddy” Combs had it all. Through the ’90s and early 2000s, he lived a life few could even dream about. He was a rich and famous music mogul with the world at his fingertips. He also had one of the world’s most beautiful women on his arm at the height of her fame: Jennifer Lopez. One would think that to Diddy, she was the one that got away. However, there’s another celebrity bombshell he couldn’t quite get out of his head.
In a recently resurfaced interview from 2014, Diddy revealed it was the one and only Cameron Diaz, who recently returned to the spotlight after taking a decade off to focus on raising a family. Diddy and Diaz reportedly dated on and off from 2008 to 2012. They first sparked dating rumors when they went to the 2008 Academy Awards together, where Diaz was a presenter.
Then in 2011, Diaz is said to have rebounded with Diddy after her relationship with baseball legend Alex Rodriguez didn’t work out. At the time, reports said they were just friends but things were still physical.
According to a source from that time: “Since they first hooked up, when she’s single, she’ll booty call him.” That turned into a more public fling where the lovebirds were spotted out and about around Beverly Hills. They were seen “making out and acting romantic.”
Fortunately for Diaz it wasn’t meant to be. She eventually met the man she was going to marry: Good Charlotte singer Benji Madden. Those two met at an event put on by Benji’s brother Joel and his wife Nicole Ritchie. They got engaged the same year they met, when Diaz was 42 and Benji Madden was a spry 35.
That meant there wasn’t really any room for Diddy in Diaz’s life. She loved Benji and her new family enough that she gave up showbiz for a good, long time. Diddy, for his part, would go on to marry Cassidy, the star of that infamous beating tape which helped lead to the former music mogul’s arrest. That doesn’t mean he still doesn’t think about what could have been.
A source told US Weekly that at one point Diddy just couldn’t stop talking about Diaz and his relationship with her. “He was at a dinner and the subject turned to Cameron dating Benji Madden,” the source said. “He said, ‘If I could turn back time, things would be different!’” Even more eye-opening is the fact that he called her “the sexiest girl in the world.” He probably has a lot of time to think about how he could do things differently sitting in that jail cell.