P. Diddy and Lori Harvey
With decades of experience in the entertainment industry, Sean Combs has been linked to a number of high-profile relationships, including those with Jennifer Lopez and Jennifer Hudson. One of the lengthiest relationships, however, was with the singer Cassie.
When this relationship came to an end, the entrepreneur began dating Lori Harvey, who was his girlfriend for several years. The two had a 28-year age gap, and that may be why the relationship only lasted three months. After breaking up with Lori, P. Diddy found love in Joie Chavis, who is 18 years his junior. Before Diddy, she was seen in the arms of Bow Wow, another figure in the ‘90s to early 2000s hip-hop scene.