Jennifer Lopez has been in the news recently following the breakup of her second-round marriage with Ben Affleck. But the recent arrest of Sean ‘P Diddy’ Combs has drawn attention away from Bennifer 2.0, and to her tumultuous late 90s relationship with the recently arrested rapper and music producer.

Jennifer Lopez and Sean Combs had an on-and-off-again relationship between 1999 and 2001, between the end of J.Lo’s marriage to her first husband Ojani Noa, and her marriage to her second husband dancer Cris Judd.

As with all of Sean Combs’s celebrity relationships, from friends who attended his “white parties” to protegees like Justin Bieber, P Diddy’s relationship with Jennifer Lopez has come under renewed scrutiny. Here’s everything you need to know about J.Lo and Sean ‘P Diddy’ Combs’s relationship, and their arrests in 1999.

What Has Jennifer Lopez Said About Her Relationship With Sean ‘P Diddy’ Combs?

Jennifer Lopez was one of the many stars Sean Combs mentored during the late 90s and 2000s. They started dating in 1999, and the relationship ended in 2001. The singer and actress has talked warmly about Combs in recent years.

In a 2014 interview with Access Hollywood she said that Combs “gave me  so many cues and taught me so many things,” adding “there’s still so much mutual respect and admiration there.”

According to USA Today, these comments were prompted by news that Diddy had declared Jennifer Lopez the winner of the “best booty bum” war (the other contender was Kim Kardashian).

(Credit: Getty/Kevin Winter ) Jennifer Lopez and Sean P Diddy Combs at the 42nd Annual Grammy Awards
But Lopez’s comments closer to the time of their split were less glowing.

In 2003, J.Lo confirmed in an interview with Vibe magazine that they broke up because P Diddy cheated on her and that the relationship had caused her significant emotional distress.  “It was the first time I was with someone who wasn’t faithful,” she said, “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.” When she spoke about her short lived marriage to Cris Judd she said: “Coming out of a torrid relationship, I meet this sweet person who’s so refreshing.”

“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.”

Jennifer Lopez on Sean Comb’s infidelity.

As reported by Forbes, in Lopez’s 2024 documentary, The Greatest Love Story Never Told Lopez compared her relationship with Ben Affleck to previous relationships in which she had been “manhandled and a couple of other unsavoury things.” She didn’t specify by who.

Sean ‘P Diddy’ Combs And The 1999 New York Night Club Shooting

(Credit: Getty/Kevin Winter ) Jennifer Lopez and Sean Combs at the 1999 Vogue Fashion Awards
In 1999 a then 31- year old Comb’s was arrested following a shooting at a New York city nightclub in 1991. At the time, Combs was accompanied by his bodyguard Anthony “Wolf”, 21-year-old rapper Jamal “Shyne” Barrows and then 30-year-old girlfriend Jennifer Lopez.

As reported by Forbes, the incident started with a disagreement and ended in gunfire that left three people injured. Sean Combs and Jamal “Shyne” Barrows faced multiple charges, and Comb’s were dropped.

But, the most seriously injured person has always insisted that it was Comb’s who shot her in the face. Natania Reuben told News Nation that she is willing to have “a doctor remove part of the 9 mm bullet in my face so they can use it as evidence.”

Reuben filed a $130 million lawsuit for compensation against Combs in 2008, which was settled out of court in June 2011. Reuben maintains Combs shot her in the face. “I watched him,” she told The Daily Beast, “I saw him with my own eyes.” She said that his arrest was “the best day ever.”

What Were The 1999 Charges Against Sean ‘P Diddy’ Combs?

(Credit: Getty/Doug Kanter) Sean ‘P Diddy’ Combs arriving at trial for weapons and bribery related to a 1999 nightclub shooting
Following an altercation, Combs left the scene with Lopez and Jones. The three were involved in a police car chase.

According to the Washington Post, police found a stolen gun in the car. Both Combs and Lopez were arrested and, as reported by The Guardian, initially charged with criminal possession of stolen property. The charges against Lopez were dropped overnight, but Sean Combs and Jamal Barrow went to trial. Diddy faced additional charges of bribery; he had allegedly offered the driver of the car $50,000 to say the gun was his.

Diddy was acquitted of the charges. His 21-year-old co-defendant, Jamal “Shyne” Barrow, was charged with five offences, including first-degree assault, reckless endangerment and criminal possession of a weapon. Barrow was acquitted of attempted murder but served ten years for his charges, according to The New York Times. Nobody was ever charged and found guilty of the actual shooting.

What Did Jennifer Lopez Say About The Shooting? 

Jennifer Lopez has rarely spoken about the shooting, but, in 2000 she did address it in an interview with British ELLE. She said “it was a complete nightmare.” “I had absolutely no idea what was going on. No one did.”

J.Lo is yet to comment on the Sean Combs arrest.