The Messiest Parts Of Diddy & J. Lo's Relationship Aren't A Secret

Jennifer Lopez and Sean "Diddy" Combs' relationship history is remarkably messy — in addition to alleged infidelity, there's a shooting, police chase, and disastrous romantic gesture. J. Lo's documentary "The Greatest Love Story Never Told" also brought the exes' relationship under renewed scrutiny in the wake of Cassie Ventura's disturbing allegations about Diddy.

In her documentary, Lopez reveals that she was mistreated by one or more of her exes. "I've definitely been manhandled and a couple of other unsavory things. Rough. Disrespectful," she says. One source told the Daily Mail Lopez isn't talking about Diddy, but NewsNation quoted another insider as saying, "He definitely manhandled her, but it's a little low to bring this all up now. It's kicking a man when he's down." Months before Lopez's doc dropped, Cassie had filed a civil lawsuit accusing Diddy of physically assaulting and raping her during their relationship.

In recent years, Lopez hasn't shown any signs that she bears Diddy any ill will. She and then-boyfriend Alex Rodriguez participated in Diddy's virtual dance-a-thon in 2020, and she greeted Diddy with a hug when he attended the last show of her Las Vegas residency in 2018. "Jennifer saw Diddy in the crowd and sang to him," an attendee told the Daily Mail. But when describing what dating Diddy was like to CBS Sunday Morning in 2019, Lopez did say, "We had this kind of crazy, tumultuous relationship that ended in a bang." Its beginning was also explosive.

When they were interviewed by Essence in 2009, Diddy and Kim Porter had rekindled their on-and-off relationship. Porter had some choice words for Jennifer Lopez, dismissing her as a temporary distraction with a "big booty and a smile."

Porter was dating Diddy when Lopez appeared in his 1997 music video for "Been Around the World." After the two singers' relationship went from being professional to romantic, a furious Porter booted Diddy from their shared abode. However, she expected him to come crawling back someday. "He was still in love with me," she said. According to Porter, Diddy kept her phone ringing throughout his highly publicized romance with Lopez. Adding to the messiness of the situation was the arrival of Diddy and Porter's second child shortly before Porter learned about the affair.

Lopez's first husband, Ojani Noa, was also upset when he learned that Diddy and Lopez had started stepping out together. "I rang Jen and asked why she was going out with him on dates and she said, 'It's just business. This is what I'm being told I have to do,'" he told the Daily Mail. "I was jealous and would scream, 'But you are married!'" Lopez and Noa divorced in 1998, a year before she and Diddy walked their first red carpet together at the 1999 MTV VMAs. Explaining why he cheated with Lopez, Diddy told Essence that Porter "wasn't really conforming to how I wanted her to conform." Ick.

After fleeing from the scene of a shooting in 1999, Jennifer Lopez and Diddy were arrested. The couple had been partying at Club New York in Manhattan when Diddy reportedly got into an altercation with another patron, Matthew "Scar" Allen, over a spilled drink. Allen testified that he saw Diddy and another rapper, Jamal "Shyne" Barrow, firing guns during the resulting fray. Diddy then hopped into a vehicle with Lopez, his chauffeur Wardel "Woody" Fenderson, and his bodyguard Anthony "Wolf" Jones. The foursome led police on a short chase before giving themselves up. A gun was found in the car, and Diddy was charged with bribery and gun possession. Fenderson testified that the gun belonged to Diddy and claimed that the rapper told him, "I'm Puff Daddy — I can't take the gun," per the New York Post. He also said that Diddy offered him a bribe to tell police that the gun belonged to him, and part of the bribe was a pinkie ring Lopez had given Diddy as a gift.

Lopez was released without any charges, but not before she spent many tearful hours in custody at a Manhattan station house. To add insult to injury, a cop later took a dig at Lopez's appearance, telling the Daily News, "She's a beautiful woman, no doubt about it, but she looked kind of Plain Jane-ish." Diddy was later acquitted, while Shyne was handed a 10-year prison sentence for attempted murder.

After Jennifer Lopez testified in court, a source told the New York Post that she assured a grand jury that Diddy did not have a gun on his person when he entered Club New York that fateful night. "Look, I danced with him, I had my arms around him — no gun,'" she reportedly said. But in a 2024 civil suit, music producer Rodney "Lil Rod" Jones claims that Diddy boasted about being the gunman who shot one clubgoer in the face. That victim, Natania Reuben, has insisted that it was Diddy who shot her and not Shyne.

On "Elizabeth Vargas Reports," Reuben called for the investigation into the shooting to be reopened. She pointed to some of Jones' allegations when arguing that Diddy's involvement was worthy of a second look, specifically a claim he made about Lopez. In his lawsuit, Jones alleges that Diddy told him Lopez "carried the gun into the club for him and passed him the gun after he got into an altercation with another individual." Cassie similarly claimed that Diddy used to make her carry guns for him. In her lawsuit, she suggested that he did this "to reinforce to his young girlfriend that he was violent, powerful, and dangerous." Another parallel between Cassie and Lopez is the power dynamic in their relationships with Diddy; he was a successful record exec when he began dating both women, while they were young artists whose careers were just starting to take off.

Diddy and Jennifer Lopez couldn't make it work for several reasons, one of which was Lopez's suspicions about Diddy's nocturnal activities. She already knew he had a history of being unfaithful, and she eventually got a small taste of what Kim Porter experienced. "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," Lopez told Vibe (via Entertainment Weekly).

In February 2001, Rolling Stone published an interview with Lopez that was conducted while she and Diddy were still dating. "It's a lot," she said of their relationship. "He's said to me many times, 'I want a divorce.'" But there was no divorce attorney needed when the couple split up that same month. Diddy's Valentine to the world was his February 14 announcement that they had called it quits.

A few months later, Diddy told Vanity Fair (via Entertainment Weekly) that he tried to win Lopez back by wooing her with a chorus of cooing; he released dozens of doves outside her home. Unfortunately, some of the birds died in flight, much to the delight of a famous neighbor's dogs. Lopez heard from Halle Berry about the unwanted chew toys that plopped down in her backyard. "It was a situation," she said on "The Wendy Williams Show." The fallen fowl were symbolic of the results Diddy got; his stunt fell flat and went splat.

Celebrity photographer Selma Fonseca believes that Ben Affleck and Jennifer Lopez's magical reunion was just a ploy to get Diddy's attention. After snapping pictures of Lopez and her leading men for years, Fonseca concluded that Diddy was the love interest J. Lo had the most intense connection with. In a 2021 interview with The U.S. Sun, Fonseca even suggested that Lopez had Diddy on her mind while engaging in some PDA with Affleck. "The other day they went to paparazzi-infested Nobu Malibu and passionately made out and I think it's all an attempt to get Diddy's attention," the photog said. 

The Bennifer reboot definitely didn't escape Diddy's notice; shortly after news of the couple's reunion broke, he posted a since-deleted throwback photo of himself and Lopez holding hands on Instagram. But according to the rapper, he wasn't trying to suggest that Lopez had rekindled the wrong flame. "It wasn't no trolling involved, that's just my friend," he told Vanity Fair.

According to Diddy's former bodyguard Gene Deal, Ben Affleck was present at a party where Diddy wanted to fight Will Smith. Deal told "The Art of Dialogue" that Diddy believed Will and Jada Pinkett Smith were trying to seduce his then-girlfriend. "Puff could scrap, now, but I don't think he could beat Will Smith," said Deal. When Diddy was asked about the rumor on "Jimmy Kimmel Live!," he joked, "I don't know what you're talking about. Jimmy, I thought we was friends."