J-Lo Was ‘Scared to Death’ by This Moment When She Was Dating Diddy—Look Back at Their Relationship

1999: Diddy and JLo become a couple

Diddy and JLo became a couple after meeting on the set of her “If You Had My Love” music video.

1999: J-Lo & Diddy were arrested after a New York City nightclub shooting

Diddy and J-Lo were arrested on gun possession charges on December 28, 1999. Three people were wounded in gunfire and Diddy’s colleague Jamal Barrows was charged with three counts of attempted murder and criminal possession of a weapon. The three fled in Diddy’s car but was ultimately apprehended by police who found a gun in their car. JLo was released because she was unaware that the gun was in the car and because she cooperated with the police. Diddy was acquitted of all his charges. Nobody was ever charged and found guilty of the actual shooting. 

J-Lo rarely spoke about the incident but noted to Elle, “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.”

2000: Diddy accompanies J-Lo at the 42nd Annual Grammy Awards

Diddy went with Jennifer Lopez to the 42nd Annual Grammy Awards. When looking back at the moment that J-Lo wore that iconic green Versace dress, Diddy told Entertainment Tonight in 2017, “Just wow. 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: Diddy & JLo break up

Diddy and JLo called it quits two years after dating. Diddy’s publicist said at the time, “Mr. Combs confirmed that he and his love, Jennifer Lopez, have, in fact, broken up. He wanted to put all the rumours surrounding their relationship to rest. At this difficult time, we ask that you respect his privacy.”

2003: J-Lo opens up about her relationship with Diddy

In an interview with Vibe, J-Lo talked about how she was spiraling in her relationship with Diddy. “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,” J-Lo told Vibe 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 come back that night.” The couple officially called it quits after J-Lo had a long reflection about her adult life. “I had to think, do I want to be home with kids in 10 years wondering where somebody is at 3 in the morning?” she said.

2014: Diddy comments on J-Lo’s music video for “Booty”

In 2014, Jennifer Lopez released her song “Booty” which Diddy had all the high praises for—the song and the real thing noting that her video “is great. It’s a work of art. It’s something that will go down in history,” Diddy told Access Hollywood. “She will never give up. She’s a great friend of mine … that thing is just incredible.”

“I am so lucky to have that great woman in my history. She is one of the greatest I’ve ever seen. Go girl!” he continued, adding that they are “great as friends” and he’s “great as a fan” rather than a love interest.

When J-Lo heard about the praise, she responded, “We spent three years of our lives together, you know, almost every single day,” she said. “Seeing him involved in Revolt and all the things that he’s done as a businessman and still being so true to his music and his art trying to uplift his community in his own way, and it’s the same thing that I try to do and I feel like I learned a lot from him coming up, watching him.” She also noted that she learned many “cues” from him. “I’ll always be grateful to him for that and I love that he can be so supportive of me so many years later and there’s still so much mutual respect, admiration and love there,” she said.

2018: Jennifer Lopez and Diddy hug after her Las Vegas residency

Diddy and Jennifer Lopez embrace at the afterparty of her last show of her 2018 Las Vegas residency JENNIFER LOPEZ: ALL I HAVE.

2021: Diddy posts a throwback photo of him and J-Lo

When rumors swirled that Ben Affleck and J-Lo were reuniting once again, Diddy posted a throwback with his ex. He was called out for the timing, but swore that it was nothing. “It wasn’t no trolling involved, that’s just my friend,” the rapper told Vanity Fair. “And I don’t have nothing to say about her relationship or her life.”

2024: Suge Knight claims that Diddy’s tapes made Ben Affleck divorce J-Lo

Diddy’s longtime rival Suge Knight claimed in his podcast “Collect Calls with Suge Knight” that Diddy’s raid was a factor in Ben Affleck and Jennifer Lopez’s divorce. “I’m quite sure they [FBI] probably called. It’s a white man who got respect in the white world. I’m quite sure they said, ‘We want to show you some things about your wife,” he said.

He also commented about her involvement in the 1999 shooting saying, “And they know the fact that J-Lo lied and said that the gun was Shyne’s or whatever and sent that man to prison, destroyed his life, and she knew it was Puffy’s.”