Jennifer Lopez and Sean ‘Diddy’ Combs: Full Relationship Timeline

Jennifer Lopez and Sean “Diddy” Combs were one of Hollywood’s most talked-about couples at the turn of the millennium. Their romance kicked off in 1999 after they met on the set of Lopez’s “If You Had My Love” music video. At the time, Diddy had recently split from longtime partner Kim Porter, though they would later rekindle their relationship before ending things for good in 2007.

J.Lo and Diddy’s two-year relationship quickly became a pop culture phenomenon. Known for their glamorous red carpet appearances—like Lopez’s iconic Versace Grammy gown—the pair also navigated their fair share of drama, from legal troubles to Diddy’s alleged infidelity. Lopez later cited trust issues as a key reason for their split in 2003.

“I never caught him [cheating] but I just knew. He’d say he was going to a club for a couple of hours and then never came back that night,” Lopez told Vibe. “I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?”

Scroll through our gallery below to uncover their complete relationship timeline: