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Jennifer Lopez and Diddy’s Relationship Timeline: The Way They Were

Jennifer Lopez and Sean Diddy Combs Relationship Timeline

Jennifer Lopez and Sean “Diddy” Combs were once one of Hollywood’s hottest A-list couples.

The pair started dating after meeting on the set of Lopez’s “If You Had My Love” music video in 1999. Diddy and his on-off partner, Kim Porter, called it quits earlier that year. (They later rekindled their romance, but Porter ended things for good in 2007).

Lopez and Diddy split in 2001 after two years together. In a 2003 interview with Vibe, Lopez opened up about why they went their separate ways, telling the outlet that Diddy “wasn’t faithful” to her.

“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 came back that night,” she recalled. “I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?”

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Though they eventually became friendly with one another after their split, Lopez spoke about past abusive relationships in her 2024 documentary, The Greatest Love Story Never Told. It is unclear which ex she was referring to.

“There were people in my life who said ‘I love you’ and then didn’t do things that were kind of in line with the word ‘love.’ Being thrown around and manhandled like that is not fun,” Lopez shared in the Amazon Prime doc, which hit the streaming platform in February 2024.

She added, “I mean, I was never in a relationship where I got beat up, thank God, but I’ve definitely been manhandled and a couple of other unsavory things. Rough. Disrespectful.”

Lopez’s candid admission came a month before Diddy’s Los Angeles and Miami homes were raided by the FBI in connection to a sex trafficking investigation.

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His lawyer Aaron Dyer slammed the allegations about his client in a statement at the time, telling Us Weekly that the “unprecedented ambush” was “a premature rush to judgment of Mr. Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits.”

Scroll down to take a look back at Lopez and Diddy’s relationship.

Jennifer Lopez and Sean Diddy Combs Relationship Timeline


The couple started dating in 1999 after meeting on the set of her “If You Had My Love” music video.


Diddy accompanied the “Let’s Get Loud” singer to the 42nd Annual Grammy Awards in Los Angeles, where she donned her famous plunging green Versace gown.

Diddy later opened up about Lopez’s iconic dress while chatting with Entertainment Tonight in 2017.

Jennifer Lopez Dating History

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“Just wow,” the rapper said when recalling his ex’s look. “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.”

He added, “She deserved it. She is one of the fliest out there.”


The couple called it quits in 2001 after two years together.


In an interview with Vibe two years after their split, the Maid in Manhattan actress opened up about why she and Diddy went their separate ways, telling the outlet that being with him was “the first time I was with someone who wasn’t faithful.”

She continued, “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. 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.”

Jennifer Lopez and Sean Diddy Combs Relationship Timeline


The exes reunited at her All I Have Las Vegas residency party in 2018, where they shared a hug and chatted with Lopez’s now-ex, Alex Rodriguez.


Diddy shared a since-deleted Instagram photo of the former couple on Instagram in May 2021, simply captioning the snap, “#tbt.” One day prior, Us Weekly reported that Lopez and Ben Affleck – who dated in 2002 and called off their engagement in 2004 – were “full-on dating” again and “very happy” to rekindle their romance.

Diddy later clarified his intentions with the throwback photo, telling Vanity Fair that August, “It wasn’t no trolling involved, that’s just my friend. And I don’t have nothing to say about her relationship or her life.”

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