Check In: Diddy Briefly Dated Jennifer Lopez During a Break From His Relationship With Kim Porter

Diddy was JLo’s date when she debuted her viral, green Versace dress at the 2000 Grammy Awards. You know the one.

Ever since his arrest in mid-September, Diddy’s personal life has taken center stage. Following charges of sex trafficking, racketeering, “Freak Offs” and more, folks are trying to nail down exactly who he’s been associated with — especially in relation to his crimes. Some stars, like Usher and Ashton Kutcher, have been implicated thanks to their friendships with the music mogul, and now, even Diddy’s exes are being dragged into the mix.

At the center of a ton of recent drama is Diddy’s long-time ex-girlfriend, Kimberly Porter, who sadly passed away in 2018 — but one of the producer’s shorter-lived relationships has been placed under the microscope, as well.

For those too young to remember, Diddy dated Jennifer Lopez during a break from his high-profile romance with Kim. Let’s take a look at his and J.Lo’s relationship

Inside J.Lo and Diddy’s relationship timeline.
The year was 1999. Diddy and Kim Porter had just split, having welcomed their first son, Christian, just one year earlier. The two were embroiled in a heated custody battle for the child. Amidst all this, Diddy was tapped to work on rising pop sensation Jennifer Lopez’s “If You Had My Love” music video.

This is where the two musicians met, and things began to blossom.

Diddy and J.Lo were often spotted on nights out together, and they were considered to be something of an “it couple” at the time. One of their most famous outings, however, was a bit more dramatic than most other “it couples” — in 1999, they were involved in a shooting incident in a New York nightclub that ended with them both being arrested

While Jennifer’s charges were dropped, Diddy was forced to go to trial on charges of bribery and gun possession, though he was later acquitted.

J.Lo and Diddy ultimately called it quits in 2001.
Following the shooting, the couple fell into an on-and-off relationship that ultimately ended with a breakup on Valentine’s Day 2001 — but not before Diddy and J.Lo made their Grammy’s debut, with Jennifer donning her viral green dress. You know, the one that caused the invention of Google Images?

When asked about his ex-girlfriend’s groundbreaking fashion statement in 2017, Diddy told ET, “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.”

However, regardless of any fashion breakthroughs, the couple just couldn’t make it work and announced their breakup in February 2001 via Diddy’s publicist.

“Mr. Combs confirmed that he and his love, Jennifer Lopez, have, in fact, broken up,” she told ABC. “He wanted to put all the rumors surrounding their relationship to rest. At this difficult time, we ask that you respect his privacy.”

Diddy Briefly Dated Jennifer Lopez During a Break From His Relationship With Kim Porter
Diddy was JLo’s date when she debuted her viral, green Versace dress at the 2000 Grammy Awards. You know the one.

jlo and diddy
SOURCE: MEGA
Ever since his arrest in mid-September, Diddy’s personal life has taken center stage. Following charges of sex trafficking, racketeering, “Freak Offs” and more, folks are trying to nail down exactly who he’s been associated with — especially in relation to his crimes. Some stars, like Usher and Ashton Kutcher, have been implicated thanks to their friendships with the music mogul, and now, even Diddy’s exes are being dragged into the mix.

At the center of a ton of recent drama is Diddy’s long-time ex-girlfriend, Kimberly Porter, who sadly passed away in 2018 — but one of the producer’s shorter-lived relationships has been placed under the microscope, as well.

For those too young to remember, Diddy dated Jennifer Lopez during a break from his high-profile romance with Kim. Let’s take a look at his and J.Lo’s relationship.

Inside J.Lo and Diddy’s relationship timeline.
The year was 1999. Diddy and Kim Porter had just split, having welcomed their first son, Christian, just one year earlier. The two were embroiled in a heated custody battle for the child. Amidst all this, Diddy was tapped to work on rising pop sensation Jennifer Lopez’s “If You Had My Love” music video.

This is where the two musicians met, and things began to blossom.

Diddy and J.Lo were often spotted on nights out together, and they were considered to be something of an “it couple” at the time. One of their most famous outings, however, was a bit more dramatic than most other “it couples” — in 1999, they were involved in a shooting incident in a New York nightclub that ended with them both being arrested.

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While Jennifer’s charges were dropped, Diddy was forced to go to trial on charges of bribery and gun possession, though he was later acquitted.

J.Lo and Diddy ultimately called it quits in 2001.
Following the shooting, the couple fell into an on-and-off relationship that ultimately ended with a breakup on Valentine’s Day 2001 — but not before Diddy and J.Lo made their Grammy’s debut, with Jennifer donning her viral green dress. You know, the one that caused the invention of Google Images?

When asked about his ex-girlfriend’s groundbreaking fashion statement in 2017, Diddy told ET, “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.”

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However, regardless of any fashion breakthroughs, the couple just couldn’t make it work and announced their breakup in February 2001 via Diddy’s publicist.

“Mr. Combs confirmed that he and his love, Jennifer Lopez, have, in fact, broken up,” she told ABC. “He wanted to put all the rumors surrounding their relationship to rest. At this difficult time, we ask that you respect his privacy.”

Sean “Diddy” Combs
SOURCE: MEGA
Sean “Diddy” Combs, who is accused of assault along with his bodyguard, Joseph Sherman

Though no official statement was ever made as to why the pair split, later interviews from Jennifer hinted that infidelity on Diddy’s part, as well as lingering romantic feelings for his ex, Kim Porter, may have had something to do with it.

Following the short-lived relationship, Diddy did end up reconciling with Kim and went on to date her for several more years. J.Lo, on the other hand, began dating Ben Affleck — and we all know how that turned out.