Jennifer Lopez & Puff Daddy
The lasting image from the J-Lo and Puffy relationship is that green dress Lopez wore to the Grammys in 2000. You know the one we’re talking about. While the relationship may have seemed like a match made in musical heaven, it was actually pretty short-lived.
The couple began dating in 1999 but were split up by 2001. They did have another memorable incident in their relationship besides the Grammy’s. They were arrested together in Times Square, and as a result, Puffy went to jail for criminal possession of a weapon.