PHOTOSSean 'Diddy' Combs and Jennifer Lopez's Relationship Timeline: How It All Began, Why It Ended and More
Sean 'Diddy' Combs and Jennifer Lopez dated for two years.
1999: Sean 'Diddy' Combs and Jennifer Lopez Started Dating
Sean 'Diddy' Combs dated Kim Porter before Jennifer Lopez.
Sean "Diddy" Combs and Jennifer Lopez struck up a romance after they filmed the music video for her single "If You Had My Love." They immediately scored media attention when they made their first public appearance as a couple at the MTV Video Music Awards in September 1999.
December 1999: Sean 'Diddy' Combs and Jennifer Lopez Were Arrested
He called Jennifer Lopez one of his greatest loves.
Just a few months after they started dating, Combs and Lopez were arrested on gun possession charges following a 1999 nightclub shooting that left three people injured. Both were later acquitted of the charges.
"It was a complete nightmare from beginning to end. I was scared to death in the car. I had absolutely no idea what was going on. No one did," the Atlas actress told Elle.
2000: Sean 'Diddy' Combs and Jennifer Lopez Made a Notable Appearance at the Grammys
Sean 'Diddy' Combs moved on with Sarah Chapman after his relationship with Jennifer Lopez ended.
After the ordeal, Combs and Lopez came back stronger and attended the 42nd Annual Grammy Awards in Los Angeles, Calif. The "Let's Get Loud" singer made headlines at the time when she arrived in her famous plunging green gown.
Looking back at Lopez's iconic look, Combs told Entertainment Tonight, "We were just stepping up our game as far as what we were wearing and how we were gonna use fashion. I thought it was gonna really change the game as far as for her and fashion. I didn't know how big it was gonna be, but it was a great moment for her. She deserved it. She is one of the fliest out there."
2001: They Called It Quits
Jennifer Lopez was married to Ojani Noa for 11 months.
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Several news outlets received a press release that confirmed Combs and Lopez's breakup after two years of dating.
2003: Jennifer Lopez Broke Her Silence Over Their Controversial Relationship
Sean 'Diddy' Combs and Jennifer Lopez started dating after her divorce from Ojani Noa.
Speaking in an interview two years after the split, Lopez disclosed that the record executive's infidelity triggered them to go separate ways.
She told Vibe it was the first time she dated someone who was unfaithful, adding, "I was in this relationship with Puff where I was totally crying, crazy and going nuts, it really took my whole life in a tailspin. I never caught him but I just knew. He'd say he was going to a club for a couple of hours and then never come back that night."
2018: They Reunited Years After Their Breakup
Sean 'Diddy' Combs and Jennifer Lopez remained amicable after their split.
Combs and Lopez reunited again at her All I Have Las Vegas residency party. At the time, the exes shared a friendly hug, showing they were on good terms after their breakup.
2021: Sean 'Diddy' Combs Posted a Throwback Photo
Sean 'Diddy' Combs and Jennifer Lopez's relationship is being talked about again after his arrest.
In May 2021, Combs surprised fans when he uploaded a throwback photo of himself with Lopez after her reunion with Ben Affleck. He later took down the post.
Asked about the post, Combs told Vanity Fair, "It wasn't no trolling involved, that's just my friend. And I don't have nothing to say about her relationship or her life."
