The year 1999 was a wild time in Hollywood because it allowed couples like Jennifer Lopez and Sean “Diddy” Combs to exist. He was known as “Puffy” during that era, but it’s hard to believe the good girl from the Bronx hooked up with a rap producer who had a pretty sketchy past. Now, that Combs’ legal issues are rising to the surface after years of whispers, so is J.Lo’s two-year relationship with him.
Fans probably best remember the couple at the 2000 Grammys when Lopez wore the daring green Versace dress that plunged at the neckline and showed off her toned dancer legs. They had never seen that side of J.Lo, but that’s when a star was born. However, there was a dark side to their romance, one that the now-54-year-old performer doesn’t love to revisit because it wasn’t the easiest of relationships. 
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It was the first time I was with someone who wasn’t faithful,” J. Lo told Vibe magazine in 2003, via Entertainment Weekly. ”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 even addressed the rumors that she would often knock on hotel room doors to find her then-boyfriend. ”I can’t remember right now, but I won’t say it didn’t happen,” she explained. ”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.” Combs reportedly overlapped in his Lopez relationship with the late Kim Porter.
The anxiety-ridden situation also made her think about her romantic future. She noted, ”I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?” It wasn’t just the infidelity, though, there was a high-profile legal situation that also dominated the headlines. In December 1999, the former couple was at the Shyne nightclub in Times Square when a clubgoer started an altercation with the rapper. It led to gunfire with Lopez and Combs escaping the scene and a police chase through the city.
The cops eventually caught up to them and found what Page Six described as “a stolen and loaded 9mm semiautomatic weapon” in the car. Everyone in the vehicle was charged with weapons possession — and Lopez found herself crying in a holding cell for over 12 hours. It’s the last place she wanted to be. Even though Lopez’s charges were dropped, and Combs was acquitted, the damage was done.
Lopez has been pretty diplomatic about their time together, revealing to Access Hollywood in 2014, via Page Six, that she’s “grateful” to Combs for launching her music career. “I love that he can be so supportive of me so many years later and there’s still so much mutual respect, admiration, and love there.” We’d love to know how she feels about him now. Related story Taylor Swift Has Made This Intention Clear About Her Personal Life After Dating Joe Alwyn
Before you go, click here to see a complete timeline of Ben Affleck and Jennifer Lopez’s relationship.
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