It was 1999. Jennifer Lopez was transitioning from "the girl from Selena" to a global pop juggernaut. Sean Combs, then known as Puff Daddy, was the undisputed king of hip-hop glamour. When they got together, it wasn't just a relationship; it was a cultural shift. If you want the short answer to when did j lo date diddy, the timeline is fairly straightforward: they were a pair from roughly 1999 to early 2001.
But that’s just the Wikipedia version.
The reality was a whirlwind of diamonds, red carpets, a world-famous green dress, and a literal shootout that almost ended Lopez’s career before it truly peaked. Honestly, looking back from 2026, the intensity of their two-year run feels like a fever dream. People remember the outfits, but they often forget how much the relationship actually changed J.Lo.
The Spark: If You Had My Love
They met on a music video set. Standard industry stuff, right? Diddy was producing tracks for her debut album, On the 6. Specifically, he worked on the video for "If You Had My Love." At the time, J.Lo was freshly divorced from her first husband, Ojani Noa.
She was 29. He was 30.
They were both at this massive, hungry tipping point in their careers. For the first few months, they played the "just friends" card. Lopez even told David Letterman they were just hanging out, but the chemistry was too loud to ignore. By September 1999, after the MTV Video Music Awards, the secret was out. They were the "It Couple."
They moved through New York like royalty. Diddy was known for his "White Parties" and his "Bad Boy" lifestyle, while J.Lo was the Bronx girl making it big. It felt like a match made in tabloid heaven.
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That Night at Club New York
Everything changed on December 27, 1999. This is the part of the story that people still whisper about. The couple was at Club New York in Times Square when a fight broke out. Shots were fired. Three people were injured.
In the chaos, Diddy and J.Lo fled the scene in a Lincoln Navigator. They didn't get far. Police pulled them over after they allegedly ran a red light, and a stolen gun was found in the vehicle.
Imagine that today. A global pop star and a rap mogul handcuffed in the back of a squad car.
J.Lo spent 14 hours in a jail cell. She was eventually released, and the charges against her were dropped, but the trauma remained. Diddy, on the other hand, went to trial for bribery and gun possession. He was eventually acquitted in March 2001, but the damage to the relationship was already done.
The Green Dress and the Infidelity Rumors
Despite the legal drama, they stayed together through most of 2000. This was the year of the Grammy Awards. You know the one—the green Versace dress with the neckline that plunged past her navel. Diddy was on her arm that night. It’s one of the most iconic images in fashion history, and it literally led to the creation of Google Images because so many people were searching for it.
But behind the scenes, things were crumbling.
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Lopez later admitted that the relationship was "emotionally exhausting." In a 2003 interview with Vibe, she got real about why they couldn't make it work. She talked about his infidelity. She never caught him in the act, she said, but she just knew.
"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," she confessed.
She described a pattern of him saying he was going to a club for a few hours and then just... never coming back that night. It was the first time she had ever been with someone who wasn't faithful, and it clearly shook her.
When Did J Lo Date Diddy? The Final Breakup
The end came officially on Valentine’s Day, 2001. Talk about a bad date for a breakup. Diddy’s publicist released a statement confirming they had split.
Why then?
The trial was wrapping up, and the stress was immense. J.Lo was also starting to distance herself from the "Bad Boy" image. She needed stability. Shortly after, she met backup dancer Cris Judd on the set of her "Love Don't Cost a Thing" video. She married him later that year, which many saw as a direct reaction to the chaos of the Diddy years.
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The Long-Term Impact
It’s interesting to see how J.Lo talks about him now. In 2024 and 2025, during interviews about her documentary The Greatest Love Story Never Told, she alluded to "unsavory" things in past relationships. While she didn't name names, fans were quick to point toward the Diddy era.
Yet, for years, they seemed to be on good terms. Diddy even complimented her "booty" on Instagram in 2014, and they were seen hugging at a 2018 after-party.
But as Diddy's legal troubles have mounted in recent years—including his federal trial in May 2025—the public's view of their 1999-2001 era has darkened. People are looking back at that nightclub shooting with fresh eyes. Was she a victim of the environment he created? Or was she just a woman in love with the wrong guy at the wrong time?
What You Should Take Away
If you're tracking the history of Jennifer Lopez, the Diddy years represent her "wild era." It was when she went from a talented actress to a legendary persona.
Here is the reality of their timeline:
- Spring 1999: Met during the "On the 6" recording sessions.
- September 1999: Went public after the MTV VMAs.
- December 1999: Arrested together after the Club New York shooting.
- February 2000: The iconic Grammy dress moment.
- February 2001: The official Valentine's Day breakup.
The biggest lesson here is about the cost of fame. J.Lo survived that era because she had the drive to pivot. She moved on to Ben Affleck (the first time), Marc Anthony, and eventually back to Ben. But the 1999-2001 window remains the most explosive chapter of her life.
To understand J.Lo’s current career choices, you have to look at the "tailspin" she mentioned. She values peace now because, for two years at the turn of the millennium, she had none.
If you’re researching this to understand the current legal headlines surrounding Sean Combs, the best next step is to look into the specifics of the 2001 trial testimony. Many of the details coming out today in 2026 echo the testimonies from the weapons and bribery charges he faced while dating Lopez. Understanding the "Club New York" incident provides essential context for the patterns being discussed in the media today.