8. Sarah Chapman
Diddy’s relationship with Sarah Chapman has been a source of media frenzy and plenty of drama over the years since he was involved with her at the same time he was involved with his main lady Kim Porter. At one point Chapman was pregnant with her second child with Diddy at the same time that Porter was pregnant with twins while with him. Diddy tried to deny that it was his child, but a DNA proved him wrong and clearly got him in big trouble. She has since come forth with a tell-all interview that claims she was never trying to step on Porters’ toes and that she and Diddy are just friends.
7. Sienna Miller
Sienna Miller is a model, actress and fashion designer of American and British nationality. She is famous for many of her big screen roles and also for her relationship and failed engagement to Jude Law. She and Law split up because of his highly publicized relationship with the nanny of their children. Soon after their separation, she was spotted hanging out and partying with none other than Sean Diddy Combs. The paparazzi loved catching them out and loved it, even more, when they found them out for breakfast the morning after. Diddy ended his relationship with his infamous ex soon after this was publicized.
6. Penelope Cruz
The famously stunning and sexy model and actress Penelope Cruz is rumored to have had relations with Diddy in the summer of 2007. She is known for her many strongleads and supporting roles in top movies. She is also known for her charity work and volunteering in Uganda, India, and Nepal. The two had been known to be close friends since about 2005, but the rumors didn’t start until later. At the time, she was supposedly being fought over by Diddy and his buddy Pharrell but Diddy seemed to have the upper hand since he had her ride with him to a Prince concert and the two were seen getting pretty cozy that night.
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