The Insane True Story of Diddy & JLo, Explained

The Insane True Story of Diddy and JLo Explained

Welcome to MsMojo, and today we’re taking you back to when Diddy met JLo and the rollercoaster of a relationship that ensued.

Part One: If You Had My Love

The year was 1999. Sean ‘Diddy’ Combs was still going by Puff Daddy with his second studio album, “Forever,” on the horizon. Jennifer Lopez, meanwhile, was better known as a dancer and actress. Two years earlier, Lopez appeared in Diddy’s “Been Around the World” music video and starred in the biopic “Selena.” Her portrayal of Selena Quintanilla Pérez marked a stepping stone to music followed by the release of her debut album, “On the 6.” In addition to serving as one of the album’s producers, Diddy was featured on the track “Feelin' So Good.” He was also heavily involved in the music video for Lopez’s lead single “If You Had My Love,” suggesting a website theme as the dot-com bubble neared its peak.

Rumors started circulating that Diddy was dating Lopez, whose marriage to Ojani Noa had recently ended. Although Lopez initially told talk show hosts like David Letterman that Diddy was just a friend, their relationship became official following the MTV Video Music Awards in September 1999. With Diddy becoming a music mogul and Lopez being a rising superstar, the courtship was bound to attract media attention. Less than a year into the relationship, Diddy and Lopez were in the spotlight for more notorious reasons.

Part Two: I’ll Be Missing You

On December 27, 1999, Diddy and Lopez were at a Times Square nightclub with Bad Boy Records artist Shyne. Diddy and Shyne reportedly entered a confrontation with felon Matthew “Scar” Allen, all three drawing firearms. Gunshots were heard with three bystanders being injured. Diddy, Shyne, and Lopez were arrested, although the latter was quickly released without facing any charges. Diddy and Shyne were both indicted, however. Despite the negative press, Lopez and Diddy managed to overshadow the shooting headlines with an iconic red carpet moment. The following February, the couple attended the 42nd Annual Grammy Awards. Diddy draped himself in a gray and white suit, but all eyes were on Lopez’s green Versace dress.

Defined by its tropical pattern and deep neckline, the dress became instantly recognizable and a symbol of Lopez’s coronation into the A-list. Up until this point, some might’ve argued that Lopez was riding on the coattails of Diddy’s success. Seeing Lopez slay the red carpet, though, she was the one making him look good. Whether intentional or not, their Grammys appearance sent a message: the gun trial isn’t going to hold us down. That said, the charges weren’t going away. Diddy recalled being scared leading up to the trial’s verdict in March 2001. While Diddy was acquitted, Shyne got the short end of the stick, serving almost a decade in prison.

Since being released in 2009, Shyne has returned to his birthplace of Belize where he’s become a political leader. The gun trial essentially ended his friendship with Diddy, who was also down one girlfriend. A month before Diddy was cleared of all charges, his two-year relationship with Lopez ended. We’d be surprised if the shooting and trial didn’t put a strain on the relationship. According to Lopez, though, infidelity was at the root of their breakup, saying it was “the first time [she] was with someone who wasn’t faithful.” While Lopez didn’t catch him cheating, she could sense what Diddy was up to every night he didn’t return home. Lopez remembered crying and feeling she was “going nuts,” conceding that Diddy would never fully commit.

Diddy wasn’t quite ready to give up on Lopez, sending her 100 white doves and 100 pink balloons. He also asked singer Luther Vandross to serenade her and had employees “camp outside MTV’s TRL studios with signs to win [Lopez] back.” Lopez wasn’t swayed and both went their separate ways. Diddy got back together with his ex Kimberly Porter for a period. Lopez married backup dancer Cris Judd in September 2001, although they divorced in 2003. Before her marriage ended, Lopez entered a relationship with Ben Affleck. Even as the Bennifer saga came to define her love life, Lopez received questions about Diddy. Lopez often described Diddy as a friend and mentor in interviews that admittedly play differently through a modern lens.

Still, one can see how Diddy influenced Lopez’s career and business instincts. Like Diddy, Lopez didn’t stop with music, launching beauty and fashion lines. Lopez wasn’t just an actress, dancer, or singer. She was a brand. Between Lopez’s media ventures and new romances, her relationship with Diddy became an afterthought. Diddy still came up on occasion. In 2015, Wendy Williams asked Lopez if she would ever get back together with Diddy. Let’s just say Lopez’s mother didn’t approve. The two nonetheless seemed to be on good terms in 2018 when Diddy attended Lopez’s “All I Have” Vegas party. During the 2020 pandemic, Lopez and Diddy participated in an Instagram Live dance-a-thon charity.

After Lopez rekindled her relationship with Affleck in 2021, Diddy seemingly threw shade with a throwback photo of himself and his ex on Instagram. After deleting the pic, Diddy stated, “I don’t have nothing to say about her relationship or her life,” calling Lopez his “friend.” Although there seemed to be no ill will, Lopez’s relationship with Diddy was put under a microscope again with the release of her 2024 documentary, “The Greatest Love Story Never Told.” In the doc, Lopez said she “was never in a relationship where [she] got beat up,” but had “definitely been manhandled.” While Lopez didn’t name names, it was hard not to think of Diddy as he became the face of an abuse scandal.

Part Three: Bad Boy For Life

Shortly before Lopez’s documentary dropped, Diddy faced a sexual assault lawsuit from his ex, Cassie Ventura. Despite settling out of court, footage of an altercation between Ventura and Diddy effectively destroyed the latter’s image. The abuse claims and lawsuits didn’t stop with Ventura either. More than a hundred people have pursued legal action against the music mogul. The controversy has not only reshaped how the public views Diddy, but has also raised questions about those closest to him.

Months before Diddy’s arrest, Lopez and Affleck separated. Diddy’s longtime rival and convicted felon Suge Knight theorized the FBI found compromising videos of Lopez during a home raid. Knight believes Lopez lied during the 1999 gun case, sparing Diddy from prison and selling out Shyne. That’s supposedly why Affleck wanted out of their marriage, although Knight provided no evidence backing up these accusations. Rodney “Lil Rod” Jones has also claimed that Diddy used Lopez to smuggle the gun into the club. Amid Diddy’s arrest, an old photo resurfaced depicting him in bed with Lopez, Aaliyah, and several others at a 2000 party. The context of the photo is unclear, but it epitomized a question on everyone’s minds: How many people were in bed with Diddy?
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If the allegations about Diddy’s infamous white parties and freak-offs are true, it’d take a village to keep a secret like this under wraps. Lopez has remained quiet thus far, although an insider says she’s “horrified by all of the accusations” against Diddy. The unnamed source added, “She and Diddy had talked about marriage at one point, but she left him for a reason. Now people want to know why and what she saw.” We still don’t know what Lopez might’ve seen during those two years. According to the insider, though, “there were many wild moments with Diddy.” Lopez was apparently afraid to leave Diddy - receiving death threats - and is creeped out that she stayed with him for so long.

As highly publicized as their relationship was, many questions about Diddy and JLo remain unanswered. Was Lopez a victim of Diddy’s alleged abuse? Did she witness him inflicting abuse toward others? Was Lopez aware of the sex trafficking and racketeering that supposedly took place? We may never know… unless Lopez is called to testify at Diddy’s trial. For now, the early 2000s seem like a simpler time when he was Puff Daddy, she was Jenny from the Block, and the discharge of firearms was as shocking as celebrity scandals got.

What do you make of Diddy and JLo’s relationship? Let us know in the comments.