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Sean ‘Diddy‘ Combs and Jennifer Lopez have a long history dating back to the late 1990s. The former hip-hop and R&B power couple met on the set of J.Lo’s music video for ‘If You Had My Love’ in 1999 and went on to date until 2001.

Diddy, who was fresh out of his relationship with Kim Porter, went on to become a big part of Lopez’s debut album On the 6, which was released in 1999. He produced the song ‘Feelin’ So Good’, which featured Big Pun and Fat Joe.

At the time of their relationship, Diddy and J.Lo were one of the biggest celebrity couples through their romance, red carpet appearances and controversies. On December 27th, 1999, Diddy and Lopez were at a nightclub in Manhattan when a fight broke out, with gunshots being fired and three people getting injured. The couple, along with bodyguard Anthony ‘Wolf’ Jones, quickly fled the scene and were chased through the New York City borough.

When the police eventually stopped them, Lopez and Diddy were taken into custody; she was released and cleared of the charges, while Diddy was indicted on gun possession. However, he went on to be acquitted after a trial that lasted a week. Bad Boy rapper Shyne ended up spending 10 years in prison after being convicted of assault and unlawful possession of a weapon.

Diddy and J.Lo broke up in 2001, with the rapper issuing a statement through his publicist confirming the news. “Mr. Combs confirmed that he and his love, Jennifer Lopez, have, in fact, broken up,” the statement read. “He wanted to put all the rumours surrounding their relationship to rest. At this difficult time, we ask that you respect his privacy.”

The ‘I’ll Be Missing You’ rapper once claimed that he only dated Lopez to make Porter jealous and want him back in her life. “Jennifer was my perfect match in terms of energy,” he told Essence. “I thought, ‘I’ll test the waters and hopefully Kim will see I’m serious and come running after me.” Porter, who passed away in 2018 of pneumonia, was the mother of his three children, Christian, and twin daughters, Jessie and D’Lila.

Lopez addressed her breakup with Diddy in 2003, citing infidelity as the main reason for them parting ways. ”It was the first time I was with someone who wasn’t faithful,” she told Vibe. ”I was in this relationship with Puff where I was totally crying, crazy and going nuts. It really took my whole life in a tailspin.”

She added, ”I never caught him but I just knew. He’d say he was going to a club for a couple of hours and then never come back that night. I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?”

Her first husband, Ojani Noa, blamed Diddy for their divorce. During an episode of Despierta América, Noa said that J.Lo had begun working closely with Diddy in New York on her first album during the fallout of their marriage; at the time, Noa was in Los Angeles working at Lopez’s Madre’s restaurant. “There, in that distance, in that separation, was where the deception started,” he said.

Many people have questioned whether Lopez was aware of Diddy’s alleged crimes, with the rapper currently detained in Brooklyn on sex trafficking and racketeering charges. He’s also been hit with dozens of sexual assault charges on top of that.

One of her former staffers claimed that she was clueless about his actions, writing on Threads, “If you knew Jennifer Lopez, if you ever worked with her like I did, or if you were close with people who are like family to her like I am, you would know she did not have any idea about Diddy. She barely drinks, she is not a partier, she isn’t a good time girl, she is a workaholic who uplifts [women] and who was charmed by him for a brief time in her life.”

Photos recently resurfaced of Diddy’s 2000 VMAs after-party, showing J.Lo arguing with Diddy on the night he allegedly raped a 13-year-old girl alongside Jay-Z. The lawsuit, filed on December 8th, claimed a female celebrity was in the room at the time of the assault, although there’s no evidence suggesting it was Lopez.