Who: Three-time Grammy winner Sean Combs, 49 (aka P. Diddy, Puff Daddy, Diddy, Puffy, Brother Love, and briefly Swag), and Golden Globe and Grammy-nominated singer and actress Jennifer Lopez, 49 (sidebar: How has this woman not won a Grammy?!).
How They Met: Sean (Puff Daddy at the time) and Jennifer began dating around the release of Lopez’s debut album On The 6, which came out in the summer of ’99. J. Lo had recently finalized her first divorce after wedding actor Ojani Noa in 1997.
Why We Loved Them: Jen and Diddy had their own exclusive White Party on the VMA’s red carpet in 2001 and fashion has never again reached such heights.
When They Peaked: Lopez’s plunging Versace gown was so jaw-dropping that it actually inspired the creation of Google Images. And OK, Diddy probably didn’t have a lot to do with that, but his presence kind of counts for something. He told Entertainment Tonight he thought the daring gown “was gonna really change the game as far as for her and fashion,” and he was right on the money.
Where to begin …
In late December of 1999, Lopez and Combs found themselves in legal trouble after a night out in N.Y.C. evolved into a dance club shooting that left three people seriously injured.
According to New York Magazine, Puffy accidentally knocked a drink from the hand of one of the club’s patrons, instigating a verbal and physical fight that quickly escalated into a shoot-out.
Combs and Lopez were arrested after fleeing the scene with a gun in the trunk of their Lincoln Navigator. The charges against Jen were soon dropped, but it’s unclear exactly how soon that was — according to an inflammatory front page from the New York Daily News, Jen’s “Night In Hell” culminated in 14-hours spent in jail. Other sources reported that Lopez was released after just one hour. The arrest drama buoyed a stream of endless breakup rumors until their ultimate split in 2001.
Puff Daddy, represented in part by former O.J. Simpson defense lawyer Johnnie Cochran, was eventually acquitted as well — but not before he and Jen had called it quits. Just one month ahead of his trial, Sean released a statement confirming that he and his “love” had broken up. Fun fact: the entire incident inspired the era of P. Diddy. After his acquittal, the rapper told MTV News there was “no more Puff Daddy.”
Though the legal proceedings no doubt put a strain on their relationship, Jen claims that wasn’t the true source of their issues. In 2003, Lopez told Vibe that her relationship with Diddy marked “the first time I was with someone who wasn’t faithful.”
“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,” Lopez continued, “I never caught him [cheating] 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.”
J. Lo’s “torrid” relationship with Diddy made her reevaluate her future, and ultimately led her to husband no. 2, Cris Judd. “I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?” she shared.
Infidelity aside, Lopez and Combs remain ridiculously friendly. Diddy isn’t afraid to admit that Jen was “without a doubt” one of his great loves, and he even “absolutely approves” of her current beau Alex Rodriguez. The exes have been spotted together at various functions throughout the years, most recently at the final performance and after-party for Lopez’s Las Vegas residency.
Where They Are Now:
Combs has released three albums since his and Lopez’s split. The rapper even edged into his ex’s territory in 2008 when he received critical acclaim for his role in the made-for-TV adaptation of A Raisin in the Sun.
Though Combs never married, he has six children — four of which he shares with the late Kim Porter (Quincy, 27, Christian, 20, Jessie, 11, and D’Lila, 11). He shares his oldest biological son (Christian, 24) with fashion designer Misa Hylton Brim. Diddy also has a 12-year-old daughter, Chance, with Sarah Chapman.
After finalizing her divorce from Judd, Lopez had a whirlwind relationship with then-fiancé Ben Affleck before they called things off in early 2004. Jen quickly moved on, marrying singer Marc Anthony, with whom she welcomed twins (Max and Emme, both 10) in 2008. After their marriage ended in 2011, Lopez dated back-up dancer Casper Smart and was rumored to have had a fling with Drake before she got together with (in my opinion, the love of her life) retired MLB star Alex Rodriguez.
Since splitting from Diddy, Lopez’s career has flourished. The multi-hyphenate has since released six albums, 18 films (and a 19th premiering next month), starred in her own TV show, and created numerous best-selling product lines.