The Hook Up: Diddy (then Puff Daddy) and J Lo met in 1999 and engaged in a whirlwind romance that lasted for nearly two years.
The Break Up: J Lo reportedly initiated the breakup with Puff as a result of the negative press that the pair earned as a result of the Club New York shooting that Puff and his artist Shyne were involved in in 2001.
The Mess They Left: This breakup left a lot of gossipmongers wondering, 'What could have been?' Despite going through several high-profile relationships, Diddy has never married. And as recently as this year, he's said that he still loves J Lo. And who can forget his "All I touch is J Lo's" line from the recent "O Let's Do It" remix?!