Diddy and Jennifer Lopez met on the set of the music video for “If You Had My Love” off Lopez’s debut album in September 1999.

In December 1999, they were fleeing a nightclub in New York City where a triple shooting had just taken place. The couple’s Lincoln Navigator ran a red light and they pulled over. A stolen gun was found in the car.

Lopez spent 14 hours handcuffed to a bench at the police station before the charges against her were dismissed. However, Diddy was charged with battery and gun possession and went on trial. He was eventually acquitted of all charges in January 2001.

The whole incident put a big strain on their relationship, but Lopez stood by Diddy while he was on trial. They even attended the 2000 Grammy Awards together after the incident.