You remember that green Versace dress, right? The one with the neckline that basically ended at her belly button. It’s the dress that literally forced Google to invent Google Images because everyone was searching for it. Most people forget that Sean "Diddy" Combs (then known as Puff Daddy) was the guy standing right next to her on that 2000 Grammy red carpet.
But when did JLo date Diddy, exactly? It wasn't just a quick summer fling. It was a two-year whirlwind that fundamentally changed both of their careers. It was glamorous. It was loud. And honestly, it was kind of a mess by the end.
The Start of the "Puffy" Era
They met in 1999. Jennifer was transitioning from being a respected actress in movies like Selena to becoming a global pop star. She was working on her debut album, On the 6, and Diddy was brought in to help produce and mentor her.
At the time, Jennifer was just coming off a divorce from her first husband, Ojani Noa. Diddy was the king of the world, running Bad Boy Records and living a life of total excess. The chemistry was instant. By the time the MTV Video Music Awards rolled around in September 1999, they were the "It" couple.
They were everywhere. You couldn't open a magazine without seeing them. But behind the scenes, things were already getting heavy. Jennifer later described the relationship as "tumultuous." She was a Bronx girl who liked staying in; he was a mogul who lived for the club.
That Night at Club New York
If you want to know when things took a dark turn, you have to look at December 27, 1999. This is the moment most people point to when they ask about the JLo and Diddy timeline.
The couple was partying at Club New York in Manhattan when a fight broke out. Gunshots were fired. Three people were injured. In the chaos, Diddy and Jennifer fled the scene in a Lincoln Navigator, allegedly running red lights before being pulled over by the NYPD.
The police found a gun in the car. Both were arrested.
Can you imagine? One of the biggest stars in the world, handcuffed to a bench in a precinct for 14 hours. Jennifer was eventually cleared of all charges, but Diddy had to go through a massive, televised trial for gun possession and bribery.
He was eventually acquitted in early 2001, but the damage to the relationship was done. Being a "ride or die" is one thing, but facing potential prison time for your boyfriend's night out is a whole different level of stress.
Why They Actually Broke Up
They officially split on Valentine’s Day in 2001. Talk about a brutal day to announce a breakup.
For years, people speculated about why they ended it. Was it the shooting? Was it the fame? Jennifer finally got real about it in a 2003 interview with Vibe magazine. She admitted that she spent a lot of the relationship "totally crying, crazy, and going nuts."
Basically, she couldn't trust him.
She never actually caught him in the act, but she "just knew" he wasn't being faithful. He’d say he was going to a club for a few hours and then just... not come home. It was her first time dealing with a partner who wasn't faithful, and it took her life into a tailspin.
There was also the Kim Porter factor. Diddy was constantly on and off with Kim, the mother of his children, even while he was with Jennifer. It was a crowded relationship.
A Quick Timeline of the Relationship
- Summer 1999: They meet while working on her music.
- September 1999: Make it official at the MTV VMAs.
- December 1999: The infamous nightclub shooting and arrest.
- February 2000: The iconic Green Versace Dress at the Grammys.
- February 2001: The Valentine's Day breakup announcement.
The Aftermath and Renewed Interest
After the split, Jennifer moved on fast. She married backup dancer Cris Judd just months later. Diddy, meanwhile, called Jennifer one of his "greatest loves" in interviews years later.
Why are we talking about this in 2026?
Because of the massive legal cloud currently hanging over Sean Combs. As his past behavior comes under the microscope, people are looking back at every woman he’s ever been with. Jennifer has mostly stayed silent about the current allegations, but the history is there.
She’s often called the "one that got away" for him, but for her, it seems like a period of her life she’s happy to leave in the rearview mirror.
What This Means for Us Now
Looking back at the JLo and Diddy era is a masterclass in how much a relationship can impact a personal brand.
For Jennifer, it was her "rebel" phase that established her as a music powerhouse, but it also nearly derailed her career. For Diddy, it was the peak of his social influence.
If you’re looking for lessons here, it’s basically this:
- Trust your gut. If you feel like someone isn't being faithful, you're usually right.
- Separate your business from your heart. Mixing a producer role with a romantic one made their split messy and public.
- Know when to walk. Jennifer realized she couldn't have the family life she wanted with someone who lived at the club until 4 AM.
If you want to understand the full context of their history, it’s worth looking at Jennifer's later interviews where she discusses her "self-worth journey." She’s spent decades trying to figure out why she picked the men she did, and the Diddy years were a huge part of that puzzle.
For those tracking the current legal cases involving Diddy, keep an eye on court filings from the early 2000s. Many of the names resurfacing now were the same ones hanging around the Bad Boy inner circle during the time Jennifer was in the picture.
Watching old footage of them now feels like looking at a different world. They were the king and queen of New York, but beneath the diamonds and the white parties, it was a relationship built on shaky ground.
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Stay updated on the ongoing legal developments by checking official news outlets, as the situation surrounding Sean Combs is evolving rapidly. Understanding the timeline of his past relationships provides necessary context for the allegations being discussed today.
Check back for more updates as new details from that era continue to surface.