Jennifer Lopez and Puff Daddy

While Jennifer Lopez and Sean "Diddy" Combs didn`t publicly acknowledge their relationship until September, 1999, they were dating for months before that. Lopez was with Combs the night that his entourage got into a night club argument in New York that ended in gun fire. While Lopez was cleared of charges early on, Combs was eventually acquitted only after a two year criminal process that took a toll on the couple`s relationship. By the end, she was already rumored to be seeing back-up dancer Cris Judd.