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Jennifer Lopez and Sean “Diddy” Combs dated between 1999 and 2001 after meeting on the set of a music video. Lopez said their relationship was exciting at first, but things quickly took a turn for the worse. Early in their relationship, police arrested Lopez and Diddy for the latter’s involvement in a nightclub shooting. Lopez described the night as a nightmare.

Jennifer Lopez said she had a terrifying night out with Sean ‘Diddy’ Combs

In 1999, Lopez and Diddy were at Club New York in Manhattan when a disagreement broke out between Diddy, his bodyguard Anthony “Wolf” Jones, and rapper Jamal “Shyne” Barrow. The fight escalated and ended in gunfire, leaving three people injured. In the aftermath, Lopez, Diddy, and Jones fled with police in pursuit. They arrested Lopez and Diddy, but quickly dropped charges against her. Lopez described this as “the worst thing that ever happened to me.”

“It was a complete nightmare from beginning to end,” she told Elle Magazine in 2000, per the New York Post.

Jennifer Lopez and Sean 'Diddy' Combs walk together and hold hands. They both wear white.
Jennifer Lopez and Sean ‘Diddy’ Combs | Ron Galella/Ron Galella Collection via Getty Images

She said that neither she nor Diddy knew what was going on when gunfire broke up.

“I was absolutely terrified from the moment the whole thing started in the club,” she said. “People around me were being shot. I didn’t know what was happening. I just wanted to get out of there.”

She added that the car chase terrified her.

“I was scared to death in the car,” she said. “I had absolutely no idea what was going on. No one did.”

Lopez said that looking back, she wished the whole thing had never happened.

Jennifer Lopez said this wasn’t the only tumultuous moment in her relationship with Sean ‘Diddy’ Combs

Lopez said that the period of time surrounding the shooting was dark for her. This wasn’t the only low point in her relationship, though.

“It wasn’t a great time in my life,” she told Vanity Fair in 2011. “It was scary. And we broke up many times before that, and got back together and broke up again, and nobody knew about it. It was very tempestuous. Towards the end it was emotionally exhausting. It was good that I was young.”

After breaking up and getting back together several times, Lopez and Diddy broke up for good in 2001.

He reportedly continued to pursue her after they broke up

Following their final break up, Diddy reportedly continued to pursue Lopez. An investigation by Rolling Stone found that Diddy often continued to pursue his partners after they left him. Former Bad Boy intern Damien Vasquez alleged that Diddy made employees “camp outside MTV’s TRL studios with signs to win her back.”

Sean 'Diddy' Combs wears a suit and sits with his arm around Jennifer Lopez's shoulder. She wears a shiny halter dress.
Sean “Diddy” Combs and Jennifer Lopez | Kevin Winter/ImageDirect
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It did not work, though. Lopez felt certain that Diddy cheated on her throughout their relationship and no longer wanted to be with him.