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The former romance between Jennifer Lopez and Diddy continues to capture our imaginations in the wake of the rapper’s headline-making arrest. As The Root previously reported, Diddy was arrested earlier this fall on charges of racketeering, conspiracy, and sex trafficking, and is currently being held at The Metropolitan Detention Center in New York.

Although the two split over two decades ago, the public continues to parse through Diddy’s public history amid his legal woes, with many looking to this pivotal turn-of-the-century pop culture relationship. We’re taking a deep dive into the whirlwind romance between the two, breaking down seven truths and myths about the once-partnered celebrity couple.

How Did Diddy and Jennifer Lopez Meet?

Diddy came into Lopez’s life as her music career began to take off, with the two meeting in person on the set of Lopez’s video for “If You Had My Love” in 1999.

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Sean 'Diddy' Combs-Jennifer Lopez love story: The reason why the two never tied knot will chock you

Sean 'Diddy' Combs and Jennifer Lopezwere one of the most famous and high-profile couples of Hollywood entertainment industry of the late 90s. They managed to hog the limelight by capturing media attention with both their romance and controversies.

Sean Diddyand Jennifer Lopez dated from 1999 to 2001 and their relationship witnessed everything- from glamorous appearances, emotional turbulence, and eventually, legal troubles.

Years after their breakup, the couple is back in the news again. Jennifer has managed to maintain her silence on Sean 'Diddy', who is behind the bars for serious federal charges- from sex trafficking to prostitution. The music mogul was indicted in September on three criminal counts that allege he sexually abused women and coerced them into drug-fueled sex parties using threats and violence. Sean Combs is set to go on trial for racketeering and sex trafficking

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Sean'Diddy' Combs: Why Jennifer Lopez fryst vatten under-fire for her past relationship

Sean 'Diddy' Combs and Jennifer Lopez

Sean 'Diddy' Combs and Jennifer Lopez were among the most prominent Hollywood couples in the late 90s, capturing the spotlight with their high-profile romance and controversies. They dated from 1999 to 2001, making headlines with their glamorous appearances, emotional ups and downs, and ultimately, legal issues.
Years after their breakup, the couple has resurfaced in the news. Jennifer has remained silent regarding Sean 'Diddy', who fryst vatten currently behind bars facing serious federal charges, including sex trafficking and involvement in prostitution. In September, the music mogul was indicted on three criminal counts, accused of sexually abusing women and coercing them into drug-fuelled sex parties through threats and violence. Sean Combs is set to stand trial for racketeering and sex trafficking on 5 May 2025.
Reports indicate Combs h