Jennifer Lopez has continued her streak of silence regarding Sean “Diddy” Combs despite constantly making major headlines. At this point, it is common knowledge that the influential Latin American entertainer had a brief, at times interrupted relationship with the now-disgraced mogul from 1999 to 2001. The high-profile affair was embroiled in controversial developments in the wake of a spate of bombshell lawsuits alleging the Rappers accused of sexual misconduct came to the surface again.

Despite his arrest in September, the Bad Boy Records founder continues to pursue his ex-girlfriend, presumably as a source of emotional turmoil during an already tense period of her life – her ongoing divorce from ex-boyfriend Ben Affleck.

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Jennifer Lopez leaves book signing when asked about ex Sean “Diddy” Combs

According to emerging reports – as also highlighted by The Mirror US – Lopez recently faced a difficult situation during an autograph signing. One person in the crowd asked the dreaded question, “JLo, do you have any comments regarding P. Diddy and the allegations?” The swirling tension seemed to immediately bring the “On the Floor” hitmaker to a halt. She dodged the question, abruptly ended the book signing, distanced herself from the fans and left with her team. Many others shouted from behind, urging them not to leave, but their pleas were brushed aside. JLo was soon out of sight.

Over the years, Lopez has kept most of the details of her Diddy romance under wraps. Cut to 2024, she is one of the many Hollywood personalities keeping quiet about Combs' allegations despite her previous involvement with the embattled star. However, she has previously hinted that their personality differences were the trigger for their breakup. Despite their largely “sacred and private” relationship, one moment has notoriously gone down in history. Several industry insiders have also heavily speculated that this was the reason behind her breakup with Ben Affleck.

Additionally, Lopez and Combs' turbulent relationship was also cited as one of the triggers for her divorce from her first husband, Ojani Noa. “Jenny from the Block” was married to him from February 1997 to January 1998.

Most infamous public detail about Jennifer Lopez and Diddy's previous relationship

Diddy, now behind bars awaiting trial in 2025 on three felony charges including sex trafficking and extortion, was once implicated in the infamous New York nightclub shooting in 1999. His then-girlfriend Lopez, bodyguard Anthony “Wolf” Jones and former protégé Jamal “Shyne” Barrows accompanied him at the time. Combs and JLo were arrested and initially charged with criminal possession of stolen property when they fled the scene with Jones and became involved in a police car chase. A stolen gun was found in the car.

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Charges against Lopez were dropped overnight, but Combs and Shyne appeared in court on multiple charges. Ultimately, Diddy was acquitted of the allegations. However, his co-defendant was charged with five felonies, including first-degree assault, reckless endangerment and criminal possession of a weapon. Although Barrow was acquitted of attempted murder, he served 10 years in prison, according to the New York Times.

In a rare moment in 2000, JLo spoke about the shooting, calling it a “complete nightmare” and that she “had absolutely no idea what was going on. Nobody did.” As a result, no one was found guilty of the actual shooting , although Natania Reuben, who insisted that Combs shot her in the face, filed a $130 million lawsuit against Combs in 2008. Although the matter was eventually settled out of court in June 2011, Reuben has been vocal about Combs' alleged active role in the shooting.

Cut to today: Texas attorney Tony Buzbee is leading the charge and plans to file 120 lawsuits against Diddy over allegations of sexual misconduct on behalf of his clients, including minors. While the rapper is locked up in Brooklyn, the lawyer continues his attack, recently filing two new lawsuits accusing the Bad Boy Records manager of sexually abusing underage boys ages 10 and 17 during auditions.