Suge Knight’s recent claims about Sean ‘Diddy’ Combs being behind the Jennifer Lopez and Ben Affleck divorce have sparked renewed interest in Diddy’s highly publicized romance with Lopez. Their relationship, which dominated headlines in the late 1990s, was filled with both glamour and controversy, capturing the public’s attention.
In September, Diddy was arrested in New York on serious charges, including sex trafficking and racketeering, landing him in Brooklyn’s Metropolitan Detention Centre as he awaits trial. That same month, Lopez announced her separation from Ben Affleck, ending their two-year marriage.
Lopez and Diddy first crossed paths in the late ‘90s on the set of her hit music video “If You Had My Love.” Their relationship quickly became a media sensation, with the two regularly appearing together at red carpet events and exclusive parties. The pair represented a blend of hip-hop and Latin crossover success, embodying the vibrant entertainment scene of the time. However, their relationship also faced significant turbulence.
One such moment was Diddy’s extravagant white parties, which became legendary. Photographer Selma Fonseca, who attended many of these gatherings, recalled a pivotal moment when she captured Lopez and Diddy sharing a kiss on a balcony at one of his Hamptons parties, which confirmed their romantic involvement to the public.
The most dramatic chapter of their relationship unfolded in 1999, during a night out at a New York club. A confrontation between Diddy, his bodyguard Anthony ‘Wolf’ Jones, and rapper Jamal ‘Shyne’ Barrow led to gunfire, leaving several injured. Both Diddy and Lopez were arrested, although Lopez was later released without charges. The scandal, however, deeply impacted her burgeoning career and placed additional strain on their already rocky relationship.
Diddy faced serious legal challenges following the incident, including charges for illegal possession of a firearm and bribery, after allegedly attempting to pay his driver to take the blame for the weapon. While Diddy ultimately avoided conviction, Barrow was sentenced to 10 years in prison. The intense media scrutiny and rumors of Diddy’s infidelity pushed Lopez to end the relationship, marking the conclusion of their two-year romance.
Looking back, Lopez has described her time with Diddy as a significant but difficult period in her life, acknowledging that their relationship, though important, was filled with a lifestyle she eventually outgrew. After the breakup, she shifted her focus toward her music and acting career. Diddy, on the other hand, has consistently spoken fondly of Lopez, referring to her as a special person in his life. The two even shared a lighthearted reunion in 2020 during a charity livestream.
Though their romance ended decades ago, the lingering impact of their relationship remains a topic of public fascination, especially as new claims bring their past into the spotlight once again.
