Sean “Diddy” Combs’ recent litany of sexual assault lawsuits and an ongoing sex trafficking investigation has put the limelight back on the “Bad Boy for Life” rapper’s past – including his high-profile romances.

Perhaps one of his most memorable relationships to date, though, was with pop superstar Jennifer Lopez.

Although the former couple only dated for two years, they went through the highest highs and lowest lows in the public eye together.

Jennifer Lopez and Sean "Diddy" Combs.
Jennifer Lopez and Sean “Diddy” Combs dated from 1999 to 2001.Getty Images

Jennifer Lopez and Sean "Diddy" Combs.
The couple had a very tumultuous relationship during their nearly three years together.FilmMagic, Inc

Sean "Diddy" Combs.
All aspects of Combs’ past are under a microscope given his recent legal issues.Xavier Collin/Image Press Agency / SplashNews.com

In 1999, when Lopez was riding the wave of her success from the box office hit “Selena,” she was preparing to release her debut album, “On the 6.”

Combs was hired to co-write and produce her track “Feelin’ So Good” featuring Big Pun and Fat Joe, which is how they met and sparks flew.

The mega producer reportedly even played a big role in how Lopez got ahold of her debut single, “If You Had My Love.”

Singer Chanté Moore previously told NPR News and Notes that Combs persuaded Rodney Jenkins to give Lopez the same arrangement that he had already been working on for her track “If I Gave Love.”


“I heard that it was because Puff Daddy walked in and heard my song and said ‘I want that song,’ and he [Jenkins] was like, ‘Well that’s already taken. We wrote that for Chanté,’ and [Combs] was like, ‘I want that song,’” she claimed.

Lopez and Combs went public with their romance for the first time in September 1999 at the MTV Video Music Awards, where the singer wore a bedazzled white crop top, white jeans and a matching bandana.

She was nominated that night for best female video, best new artist in a video, best pop video and best dance video for “If You Had My Love.”

Jennifer Lopez and Sean "Diddy" Combs.
Lopez and Combs debuted their romance at the 1999 MTV Video Music Awards.Getty Images

Jennifer Lopez and Sean "Diddy" Combs.
The pair showed PDA and held hands on the carpet.FilmMagic, Inc
Combs and Lopez continued to dominate Hollywood red carpets with their glamorous fashion moments, but the most standout appearance was at the 2000 Grammys the following February.

The “Let’s Get Loud” singer broke the internet — before that term even existed — by wearing a jaw-dropping, low cut, green Versace dress that led to the creation of Google Images.

Although most people may not remember that Combs was her date that night, Lopez did indeed walk hand-in-hand with the record executive, who wore a silver suit with a lavender hue and sunglasses.

While they appeared to be a picture-perfect couple in many ways, Lopez was secretly realizing that they had intrinsic differences regarding their interests.

Jennifer Lopez and Sean "Diddy" Combs at the Grammys.
Combs and Lopez shared an iconic red carpet moment at the 2000 Grammys.FilmMagic

Jennifer Lopez and Sean "Diddy" Combs at the 2000 Grammys.
Lopez wore an unforgettable green Versace dress that night.WireImage
“Puff loves to go out,” the “Get Right” singer told Rolling Stone for their February 2001 issue, calling Combs by his then-monicker, “Puff Daddy.”

“He’s been a going-out-to-clubs person all his life, doing his thing. I’ve always been a homebody.”

A top industry source told The Post at the time, “She wanted to end it for a long time, but she wanted to do it gracefully – especially with a guy like that, with his bad temper and high profile.”

Ironically, it was a party night out that seemingly caused the most strain in the pair’s relationship.

Jennifer Lopez and Sean "Diddy" Combs.
Lopez reportedly felt she and Combs liked two different lifestyles.MediaPunch/Shutterstock

Jennifer Lopez and Sean "Diddy" Combs.
Lopez considered herself more of a “homebody.”Paul Bruinooge/Patrick McMullan via Getty Images


In December 1999, Lopez and Combs were hanging out at Shyne nightclub in Times Square when a fellow clubgoer reportedly tossed a wad of bills at the “It’s All About the Benjamins” rapper, setting off a heated argument that broke out into gunfire.

Lopez and Combs reportedly fled the scene in a Lincoln Navigator SUV, and police had to chase them down as they sped past 11 red lights.

Once cops pulled them over, they found a stolen and loaded 9mm semiautomatic in their vehicle, and all parties were arrested on a weapons possessions charge.

Jennifer Lopez and Sean "Diddy" Combs.
Lopez and Combs were involved in a club shooting in 1999.WireImage

Jennifer Lopez and Sean "Diddy" Combs in a convertible.
They were arrested after fleeing the scene of the crime.PAY PER USE
Lopez was held in a cell for more than 12 hours where she bawled her eyes out, per police.

The “Enough” star reportedly wanted to end things with Combs then, but played the supportive girlfriend role for a while longer while his case was tried in court.

The “Can’t Nobody Hold Me Down” rapper was acquitted following the trial, and he later quietly settled civil suits with the victims for undisclosed amounts.

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Jennifer Lopez and Sean "Diddy" Combs.
Lopez recalled the shooting ordeal being a “complete nightmare.”Getty Images

Sean "Diddy" Combs.
Combs was acquitted during the shooting’s trial.ASSOCIATED PRESS
“It was a complete nightmare from beginning to end,” Lopez told Elle magazine for their July 2000 issue, reflecting on the ordeal. “I was scared to death in the car. I had absolutely no idea what was going on. No one did.”

Lopez broke up with Combs for good in February 2001, with his alleged infidelity being the final nail in the coffin.

A lawsuit filed that year claimed the “Making the Band” exec had been carrying on a sexual relationship with the now-late Kim Porter from 1995 to 2000, while he was still dating the “Wedding Planner” star.

Two years after the split, Lopez spoke to Vibe magazine about her relationship with Diddy for her 2003 cover story, admitting, “It was the first time I was with someone who wasn’t faithful.”

Jennifer Lopez and Sean "Diddy" Combs.
Combs was allegedly also unfaithful to Lopez during their relationship.Ron Galella Collection via Getty Images

Kim Porter and Sean "Diddy" Combs.
Combs allegedly cheated on Lopez with Kim Porter, the mother of three of his kids.Lester Cohen/WireImage.com
”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 also said, according to Entertainment Weekly.

At the time, Lopez further addressed claims she “hunt down” Combs at hotel rooms – and didn’t deny it.

”I can’t remember right now, but I won’t say it didn’t happen,” the “Love Don’t Cost a Thing” singer said.

”I never caught him but I just knew. … I had to think, ‘Do I want to be home with kids in 10 years wondering where somebody is at three in the morning?’”

Jennifer Lopez and Sean "Diddy" Combs.
Lopez said she broke up with Combs because she didn’t always want to “wonder” what he was up to.AFP via Getty Images

Jennifer Lopez and Sean "Diddy" Combs hugging.
The exes have remained friendly over the years.Getty Images for Caesars Entertainment