Jennifer Lopez has been in the press more recently due to the breakup of her marriage to Ben Affleck. However, the recent arrest involving hip hop mogul Sean “Diddy” Combs, an ex-boyfriend from Lopez’s past, has brought her tumultuous late 90s relationship with Diddy back into the media, with a list of all of Sean Combs’ relationships with other celebrities, friends who attended the mogul’s “White Party.”

Jennifer Lopez and Sean “Diddy” Combs were in a relationship that lasted from 1999 to 2001, between the end of J.Lo’s marriage to her first husband, Ojani Noa, and her marriage to her second husband (the other being dancer Cris Judd).

What did Jennifer Lopez say about her relationship with Sean “Diddy” Combs?

Jennifer Lopez was one of many stars mentored by Sean Combs in the late 1990s and 2000s. They began dating in 1999 and ended their relationship in 2001. The singer and actress has spoken very warmly about Combs in later years. In a 2014 interview with Access Hollywood, she said that Combs “gave me a lot of advice and taught me a lot of things,” adding that “there’s still a lot of mutual respect and admiration.”

According to USA Today, these comments came after Diddy announced that Jennifer Lopez was the winner of the “best butt” battle (with another candidate, Kim Kardashian).

But in reality, Lopez’s comments around the time she and Diddy broke up weren’t all that positive. In 2003, Lopez confirmed in an interview with Vibe magazine that they broke up because Diddy cheated on her and that the relationship caused her great emotional distress.

Sean “Diddy” Combs and Jennifer Lopez at the 42nd Annual Grammy Awards, when the two were still in love. (Photo: Getty/Kevin Winter)

She said: “It was the first time I was with someone who was unfaithful to me. I was in this relationship with Diddy. I cried and I went crazy and I went nuts, it really ruined my whole life. It became chaotic.”

Speaking about her brief marriage to Cris Judd, Lopez said: “After getting out of a passionate relationship, I met someone sweet, which was very refreshing.”

As Forbes reported, in Lopez’s 2024 documentary, The Greatest Love Story Ever Told, Lopez compared her relationship with Ben Affleck to previous relationships where she was “treated roughly and some other nasty things.” But she didn’t say who it was.

Sean “Diddy” Combs and the 1999 New York nightclub shooting

In 1999, 31-year-old Sean “Diddy” Combs was arrested after a 1991 New York City nightclub shooting. At the time, Combs was accompanied by bodyguard Anthony “Wolf,” 21-year-old rapper Jamal “Shyne” Barrows and his girlfriend Jennifer Lopez, 30.

According to Forbes, the incident began with a disagreement and ended with a shooting that injured three people. Sean Combs and Jamal “Shyne” Barrows faced multiple charges, and Combs was acquitted. However, the most seriously injured person always insisted that Combs was the one who shot him in the face. Natania Reuben told News Nation that she was willing to allow “a doctor to remove part of the 9mm bullet from my face so I could use it as evidence.”

Reuben filed a lawsuit seeking $130 million in damages from Combs in 2008, which was settled out of court in June 2011. Reuben claimed that Combs shot him in the face.

“I saw it,” she told The Daily Beast. “I saw it with my own eyes.” Natania Reuben called Diddy’s arrest “the best day of her life.”

Sean ‘Diddy’ Combs arrives for trial on weapons and bribery charges in the 1999 nightclub shooting. (Photo: Getty/Doug Kanter)

What was Sean “Diddy” Combs accused of in 1999?

After a fight, Combs left the scene with Lopez and Jones. The three were involved in a chase with a police car. According to the Washington Post, police found a stolen gun in the car. Both Combs and Lopez were arrested and, as The Guardian reported, initially charged with possession of stolen property. The charges against Lopez were dropped, but Sean Combs and Jamal Barrow appeared in court. Diddy faces additional bribery charges; he allegedly gave the car’s driver $50,000 to say the gun was his.

Diddy was acquitted. His co-defendant, Jamal “Shyne” Barrow, 21, was charged with five counts, including first-degree assault, reckless endangerment and unlawful possession of a weapon. Barrow was acquitted of attempted murder but served 10 years in prison for his crimes, according to The New York Times. In reality, no one was charged or convicted in the shooting.

What did Jennifer Lopez say about the shooting?

Jennifer Lopez rarely talks about the shoot, but in 2000 she mentioned it in an interview with British magazine ELLE. She said that “it was a complete nightmare. I had absolutely no idea what was going on. Nobody knew.”

Jennifer Lopez has not yet commented on the arrest of Sean “Diddy” Combs.