Before P. Diddy and Cassie became hip-hop’s most infamous situationship gone bad, the Bad Boy mogul seemingly kept a circle of famous women around him that he wined and dined. They were spotted with Diddy on yachts, at parties in the Hamptoms and getting cozy at award shows, which has led many to wonder how much they saw and knew about the Diddy’s alleged behavior behind the scenes.
Yes, everyone remembers when Diddy was with J.Lo, but you might have forgotten that he was also allegedly dating the following famous women.
Naomi Campbell Gave Diddy Fashion Cred
When Diddy and Naomi got together in the ’90s, the headlines were all about high fashion meeting hip-hop. It all started with the pair being photographed together several times in American and British Vogue, and though the two have never confirmed a relationship, photos of them over years reveal that they appear to be very close.
Cameron Diaz Gave Diddy Hollywood Cred
When a Hollywood A-list actress is showing up to your parties and showing you love, you’ve made it. And that’s exactly what was happening between Diddy and Cameron Diaz between 2008 and 2012. Diaz was spotted sometimes looking tipsy and very at home in Diddy’s presence. In 2014, when Diaz started publicly dating rocker Benji Madden, Diddy reportedly told a source things would be different “If I could turn back time.” He reportedly called her the “sexiest girl in the world.” But perhaps things didn’t last for the best.
Lori Harvey Rebounded With Diddy
In 2019 when Diddy, 49, was spotted vacationing in Italy with Lori Harvey,22, many social media commentators wondered if her parents knew that she was allegedly dating a man so much older than her. Well, it turns out her parents, Steve and Marjorie Harvey were right there watching the whole situation go down.
But what’s more is that Harvey was initially thought to be dating Diddy’s son Justin before she was swept off her feet by Diddy. Harvey has denied that version of events, but no one really knows what was happening behind the scenes.
Kim Porter Was His Mainstay
Even though Diddy was connected to multiple women in the music and entertainment industry, he appeared to always consider his longtime on and off girlfriend Kim Porter the queen. She had several children with Diddy, including D’Lila Star Combs and Jessie James Combs, in 2006, and Christian Combs back in 1994. So many thought that if the Bad Boy mogul was ever going to settle down, it would be with her Porter. However, when Porter died in 2018, rumors about the true nature of their relationship began to paint a different picture of Diddy.
Sienna Miller
Diddy’s connection with actress Sienna Miller started around the time he was rumored to have been trying to break it into Hollywood. Miller was fresh off of a break up, and Diddy appeared to have been looking to pair up with someone who could give him the cred he needed in Hollywood. Together they made headlines as it was reported that Diddy dumped Kim Porter to be with Miller. unlikely pair and were rumored to be dating. But like all relationships under the spotlight, Miller and Diddy insisted they were just friends who liked to party together.