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Jennifer Lopez and Sean "Diddy" Combs Throwback Pictures

Why Jennifer Lopez's Relationship With Diddy Took Her "Whole Life in a Tailspin"

September 2000
Image Source: Getty / KMazur

Jennifer Lopez may currently be dating Alex Rodriguez, but once upon a time, she and Sean "Diddy" Combs were a hot item. In fact, Diddy wasn't even known as Diddy back then — he was Puff Daddy. After her 1998 divorce from Ojani Noa, Jennifer famously dated Diddy for almost a year and a half in 1999, and together, they weathered through getting arrested and alleged infidelities on Diddy's part. And who could forget those matching white outfits?

Back in December 1999, the rapper and his girlfriend were arrested in New York and charged with criminal possession of a weapon and of stolen property in connection with a nightclub shooting. Neither Jennifer nor Diddy were injured, but two men and a woman suffered minor injuries to their faces and shoulders. The couple had been at a midtown Manhattan club when gunfire erupted at around 2:20 a.m., and they were stopped by police after they ran a red light while driving away. Police allegedly found a stolen gun in their vehicle and they were both charged with criminal possession of a weapon and stolen property, though Jennifer's count was dropped within an hour when the Manhattan district attorney decided not to prosecute her. In 2011, Diddy was finally acquitted of all the charges related to the case, and he settled with the three victims of the shooting.

In addition to their arrest, the tumultuous relationship marked the first time Jennifer "was with someone who wasn't faithful." Jennifer opened up about the split in a 2003 interview with Vibe magazine, saying, "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." During their time together, there were reports that Jennifer would hunt Diddy down and knock on hotel room doors looking for him. "I can't remember right now, but I won't say it didn't happen," she said. "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." Jennifer also explained that she and Diddy split so often that he didn't believe it when she left him for good in February 2001. "I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?" The two have since gone their separate ways but appear to be on good terms. If you're feeling nostalgic, look back on their happier times.

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