Reports suggest that Sean Diddy Combs' ex-girlfriend
Jennifer Lopez could be called for his trial more than two decades after their infamous 1999 club incident.
Now the commencement of Sean ‘P Diddy’ Comb’s trial has drawn attention away from Bennifer 2.0, and to her tumultuous late 90s relationship with the incarcerated rapper and music producer. P Diddy’s relationship with Jennifer Lopez has come under renewed interest.
Jennifer Lopez and Sean Combs had an on-again, off-again relationship from 1999 to 2001, during the period between the end of her marriage to her first husband, Ojani Noa, and her subsequent marriage to dancer Cris Judd. Jennifer Lopez and Sean Diddy Combs began dating in 1999, but their relationship ended in 2001. In recent years, Lopez has spoken fondly of Combs. In a 2014 interview with Access Hollywood, she said, “He gave me so many cues and taught me so many things,” adding that there remains “so much mutual respect and admiration” between them.
According to USA Today, these remarks came in response to Combs publicly naming Lopez the winner of a "best booty" contest, in which she was compared to Kim Kardashian. However, Lopez’s comments around the time of their breakup were notably less positive.
In a 2003 interview with Vibe magazine, Lopez revealed that the relationship ended because Combs had been unfaithful, and she described the emotional toll it took on her. “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 sent my whole life into a tailspin.” Reflecting on her brief marriage to Cris Judd, she remarked, “Coming out of a torrid relationship, I meet this sweet person who’s so refreshing.”
In her 2024 documentary The Greatest Love Story Never Told, as reported by Forbes, Lopez contrasted her current relationship with Ben Affleck to past ones in which she had been “manhandled and a couple of other unsavoury things.” She did not name anyone specifically.
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In 1999, Sean Combs, then 31, was arrested in connection with a nightclub shooting in New York City that occurred earlier that year. At the time of the incident, Combs was accompanied by his bodyguard Anthony “Wolf,” 21-year-old rapper Jamal “Shyne” Barrow, and his then-girlfriend, 30-year-old Jennifer Lopez.
According to Forbes, the altercation began with an argument and escalated into gunfire, injuring three people. Combs and Barrow were both charged, but the charges against Combs were later dropped. However, one of the victims, Natania Reuben—who suffered a gunshot wound to the face—has consistently claimed that Combs was the shooter. In an interview with NewsNation, Reuben stated she is willing to have part of the 9mm bullet removed from her face for forensic testing.
Reuben filed a $130 million civil lawsuit against Combs in 2008, which was settled out of court in June 2011. She has continued to assert that she saw Combs fire the shot, telling The Daily Beast, “I watched him. I saw him with my own eyes.” She described his arrest as “the best day ever.”
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Following the shooting, Combs, Lopez, and Barrow fled the scene and were involved in a police chase. As reported by The Washington Post, a stolen gun was found in their vehicle. Both Combs and Lopez were arrested and initially charged with criminal possession of stolen property. The charges against Lopez were dropped the following day.
Combs went to trial along with Barrow. In addition to the weapons charges, Combs faced a bribery charge for allegedly offering the driver of the vehicle $50,000 to claim ownership of the gun. Ultimately, Combs was acquitted of all charges.
Barrow, however, was convicted on five charges, including first-degree assault, reckless endangerment, and criminal possession of a weapon. Although he was acquitted of attempted murder, he was sentenced to ten years in prison, according to The New York Times. No one has ever been convicted for the actual 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.”
