Sean “Diddy” Combs and Jennifer Lopez had a 2-year relationship. However, their love affair did not end well.

Jennifer Lopez has been in the news a lot lately due to the breakdown of her marriage to Ben Affleck. However, the recent arrest of hip hop mogul Sean “Diddy” Combs – Lopez’s former boyfriend – has brought her tumultuous relationship with Diddy back into the spotlight in the late ’90s – along with a list of all the other celebrity relationships Sean Combs has had with the mogul, friends who attended his “White Party.”

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

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

Jennifer Lopez was one of many stars who was mentored by Sean Combs in the late ’90s and 2000s. They began dating in 1999 and the relationship ended in 2001. The singer-actress has spoken glowingly about Combs in recent years. In a 2014 interview with Access Hollywood, she said that Combs “gave me a lot of pointers and taught me a lot,” adding that “there’s still a lot of mutual respect and admiration there.”

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

But in fact, Lopez’s comments around the time of her and Diddy’s split were not so positive. In 2003, Lopez confirmed in an interview with Vibe magazine that they broke up because Diddy cheated on her and that the relationship had caused her significant emotional distress.

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

“It was the first time I’d been with someone who wasn’t faithful. I was in that relationship with Diddy – I was crying, I was going crazy, I was going crazy, it really turned my whole life into chaos,” she said.

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

In Lopez’s 2024 documentary, The Greatest Love Story Never Told, Lopez compared her relationship with Ben Affleck to previous relationships where she was “treated roughly and had a few other unpleasant things happen,” Forbes reported, but she didn’t specify who.

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

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

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

“I saw him,” she told The Daily Beast. “I saw it with my own eyes.” Natania Reuben said Diddy’s arrest was her “best day ever.”

Sean ‘”Diddy'” Combs arrives at court to stand trial on weapons and bribery charges in the 1999 nightclub shooting. (Photo: Getty/Doug Kanter)

What was Sean “Diddy” Combs charged with in 1999?

After a fight, Combs fled 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 initially charged with possession of stolen property, The Guardian reported. The charges against Lopez were dropped, but Sean Combs and Jamal Barrow went to trial. Diddy faces additional bribery charges; he allegedly offered the driver of the car $50,000 to say the gun was his.

Diddy was acquitted. His 21-year-old co-defendant, Jamal “Shyne” Barrow, was charged with five counts, including first-degree assault, reckless endangerment and illegal possession of a weapon. Barrow was acquitted of attempted murder but served a decade in prison for his crimes, according to The New York Times. No one was ever charged and convicted of the actual shooting.

What did Jennifer Lopez say about the shooting?

Jennifer Lopez rarely spoke about the shooting, but in 2000 she addressed 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. No one knew.”

At this time, Jennifer Lopez has not commented on the arrest of Sean “Diddy” Combs.