Diddy Shares Throwback Photo of Him and Jennifer Lopez Amid Rekindled Ben Affleck Relationship

Diddy must have been singing “I’ll Be Missing You” to himself on Thursday, May 27, when he shared a throwback photo of himself and former flame Jennifer Lopez. The post comes just days after In Touch confirmed that the “Love Don’t Cost a Thing” singer is officially back together with her old flame Ben Affleck.

Diddy (also known as Sean Love Combs), 51, posted a snap of himself and J. Lo, also 51, on Instagram in all their 2000s-era glory. The paparazzi pic showed Diddy and Jennifer looking about 20 years younger as they held hands and walked outside together.

The Bad Boy Records founder was photographed rocking his iconic gray Sean John sweatsuit, white sneakers and a baseball cap. Jennifer wore thong sandals, light wash jeans, a beige ribbed turtleneck and big brown shades.

The IT couple of the millennium began dating in 1999 after meeting on the set of a music video for her debut album, On The 6. On December 27 of that year, the Marry Me star and the frequent Notorious B.I.G. (RIP!) collaborator were arrested and charged with criminal possession of a weapon and of stolen property, after leaving the scene of a shooting at a Times Square club. Charges against Jennifer were dropped and Diddy was later acquitted.

The two split in February 2001 and she eventually moved on to Ben, 48. But there’s no bad blood between Diddy and Jen, as she spoke highly of him in a 2019 interview on The Breakfast Club. 

“The Puffy era was just kind of a crazy, heightened time in my life. You know, Puffy and I both grew up in the Bronx,” she said. “He had been in the music business and had all this success. I was just starting and making my first album when I met him. He became kind of a mentor to me in that moment. We had this kind of crazy, tumultuous relationship that ended in a bang.”

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Jennifer added that she doesn’t regret her relationship with Diddy. She even credited the Get Him to the Greek star with helping transform her music image. Diddy also produced four of her songs on her 2001 album, “J. Lo.”

Bennifer hit the scene in 2002 and lasted until 2004. However, 17 years later, Ben and Jen are dating again after her split with baseball player Alex Rodriguez. The Good Will Hunting actor has been spotted hanging with Jennifer in Miami, on a ski trip in Montana and at her Los Angeles home since mid-May.

A source recently revealed to In Touch that “Ben and Jen aren’t wasting any time” with moving forward with their rekindled relationship. “Actually, it’s like no time has passed at all. They’re right back in the thick of a red hot romance. They picked up right where they left off.”