Moment of Then: When Jennifer Lopez Dated Puff Daddy

Jennifer Lopez’s love life hasn’t exactly played out like a Nora Ephron movie, but it’s still hard to believe that she actually dated Diddy at one point in time in her life.

Lopez got with Diddy at the tail-end of the ’90s, back when he was known to his millions of fans as Puff Daddy. Their relationship fell apart shortly after a shootout at Club New York on Dec. 27, 1999, in which police found weapons inside their car. Diddy was arrested on possession charges and was later found not guilty.

Of course, they were also together for some high points, too — like the time J-Lo wore that Versace dress to the 2000 Grammys. Then there was this photo particular photo, taken at the ’99 MTV Video Music Awards, which pretty much sums up their entire relationship.