Jennifer Lopez and P. Diddy at the MTV Video Music Awards on September 7, 2000
After divorcing Ojani Noa, Jennifer immediately began dating hip hop mogul Sean Combs (aka P. Diddy). Unfortunately, the high-profile relationship was not meant to be. In December of 1999, the couple was arrested over a nightclub shooting in New York. Jennifer and P. Diddy called it quits soon after and she later described the shooting as "one of the worst nights of my life."