Jennifer Lopez and Diddy’s Relationship Timeline: The Way They Were

Jennifer Lopez and Sean 'Diddy' Combs' dated from 1999 to 2001

WireImage Jennifer Lopez and Sean “Diddy” Combs were once one of Hollywood’s hottest A-list couples. The pair started dating after meeting on the set of Lopez’s “If You Had My Love” music video in 1999. Diddy and his on-off partner, Kim Porter, called it quits earlier that year. (They later rekindled their romance, but Porter ended things for good in 2007).

Lopez and Diddy split in 2001 after two years together. In a 2003 interview with Vibe, Lopez opened up about why they went their separate ways, telling the outlet that Diddy “wasn’t faithful” to her. “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,” she recalled. “I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?”

Though they eventually became friendly with one another after their split, Lopez spoke about past abusive relationships in her 2024 documentary, The Greatest Love Story Never Told. It is unclear which ex she was referring to. “There were people in my life who said ‘I love you’ and then didn’t do things that were kind of in line with the word ‘love.’ Being thrown around and manhandled like that is not fun,” Lopez shared in the Amazon Prime doc, which hit the streaming platform in February 2024. She added, “I mean, I was never in a relationship where I got beat up, thank God, but I’ve definitely been manhandled and a couple of other unsavory things. Rough. Disrespectful.” Lopez’s candid admission came a month before Diddy’s Los Angeles and Miami homes were raided by the FBI in connection to a sex trafficking investigation.

His lawyer Aaron Dyer slammed the allegations about his client in a statement at the time, telling Us Weekly that the “unprecedented ambush” was “a premature rush to judgment of Mr. Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits.” Scroll down to take a look back at Lopez and Diddy’s relationship.