Year: 2000

Cause: At one point in time, Diddy and J.Lo were hip-hop's, if not all of pop culture's, premier power couple. The relationship's highlight happened when the couple attended the 2000 Grammys together where Jennifer wore some dress or something (VERSACE!). Ultimately the relationship fell apart due to Diddy's alleged infidelity. Can't turn a Bad Boy good, we guess. 

Currently: As most people do after a breakup, they have moved on. Jennifer Lopez has dated many a person and has had children while Puff has Cassie. What remains? Endless pics of J.Lo in that dress and an excuse for Diddy to ceaslesly brag about it.