In August 2024, Jennifer Lopez dropped a bombshell that she was divorcing her ‘greatest love,’ Ben Affleck, on their second wedding anniversary.
One month later, Sean “Diddy” Combs was arrested in New York City. He was charged with disgusting crimes against defenseless people, including his former girlfriend, Cassie Ventura.
Many of us remember when JLo and Diddy were allegedly a serious item two decades ago. Did their breakup have anything to do with his secret life?
RELATED: The Tragedy of JLo’s Kids
The JLo and Diddy relationship lasted two years, from 1999 to 2001. Their romance is once again a search term on the Internet. Outlets like Hollywood Life are warming the old tea back up to spill it again.
Hollywood Life got right to it when they reminded us that JLo and Diddy “broke up once infidelity rumors started to swirl.” They dished on everything related to “the former couple” who “apparently had a rollercoaster relationship.”
Shockingly, JLo’s mom had a hunch that something was up with Diddy. Hollywood Life claimed she “disapproved of their romance” from the start.
You have to hand it to JLo’s mom, Guadalupe Rodríguez, for knowing the real truth back then. This includes the crazy moment when JLo was by Diddy’s side, and they both got arrested.
JLo and Diddy Were Chased by the Police
Hollywood Life reported that Diddy and JLo “were arrested in December 1999.” They’d been enjoying a night out at Club New York when Diddy “got involved in an argument” with a rapper named Jamal “Shyne” Barrow.
Diddy’s bodyguard, Anthony “Wolf” Jones, was also by his side at the club. After the fight broke out, Diddy, JLo, and Wolf took off and “were chased by police.”
Hollywood Life got another bombshell from an old report in Forbes. Allegedly, law enforcement “found a stolen [weapon] in the car” that Diddy and JLo were in. They “were subsequently arrested on weapons and bribery charges.”
Jennifer’s charges “were promptly dropped,” and Diddy was acquitted of his charges in 2001. You have to wonder if Diddy will have the same luck in court this time.
Hollywood Life repeated that JLo and Diddy “broke up in February 2001 once rumors of his infidelity began to circulate.” The outlet wrote that Diddy never confirmed the cheating rumors, but JLo exposed more in an interview with Rolling Stone.
JLo Used to Be a Homebody
JLo spoke with Rolling Stone in the months following her breakup with Diddy. Hollywood Life wrote that Diddy “went by Puff Daddy at the time.” JLo claimed that she and Puff “had different ways of thinking.”
JLo offered a crazy explanation to Rolling Stone. If she were telling the real truth, Ben might have preferred to marry that version of JLo.
According to JLo, Puff Daddy loved to “go out” when they were together. Shockingly, she told Rolling Stone she was “more of a homebody.” That’s not the image we have of JLo today.
It’s common knowledge now that JLo craves the spotlight and always prefers to be out. On the other hand, Ben is infamously more private, so he’s the real “homebody.” It’s crazy that JLo described herself that way so long ago before she fell for Ben.
Wendy Williams Wanted JLo and Diddy Back Together
It took a couple of years after her split from Diddy for JLo to drop another bombshell. This time, Vibe was interviewing her, and JLo exposed a gut feeling she had about Diddy cheating, even though she told Vibe that she never actually “caught him.”
JLo revealed that Diddy would often tell her he was going to a club for a couple of hours, but he would “never come back that night.” She confessed that it was the “first time” she’d been seriously involved with a guy “who wasn’t faithful.”
It sounded like JLo’s relationship with “Puff” became a nightmare. She complained to Vibe that she was “totally crying,” she felt “crazy,” and that she was “going [more] nuts.” JLo added, “It really took my whole life in a tailspin.”
Hollywood Life jumped forward to 2015 when JLo appeared on The Wendy Williams Show. Since Diddy was recently thrown in jail, the Internet dug up this nine-year-old interview with JLo and Wendy.
Wendy always loved stirring the pot with her guests and firing up old rumors. Wendy put JLo on the spot when she claimed she’d “always” pictured JLo and Diddy getting back together.
JLo looked awkward, and the audience went nuts. However, one person was there who had inside information, and they obviously disapproved of Wendy’s suggestion.
In case you didn’t guess, Guadalupe was sitting in the audience listening to Wendy tell JLo she should get back with Diddy. JLo could only laugh with embarrassment. Guadalupe waved off the comment like she thought Wendy was nuts, and she had a disgusted look on her face.
JLo May Have Shaded Diddy in Her Documentary
In March 2024, JLo was still officially married to Ben, and Diddy was still a free man. However, storm clouds were brewing for both of them.
Media outlets like Stylecaster took another look back at JLo and Diddy’s bad romance. Shockingly, Stylecaster alleged that Diddy treated JLo “rough” and disrespectfully. Could this be the real truth, and if so, did JLo experience trauma like Diddy’s other victims?
Stylecaster made that huge assumption based on JLo’s “2024 documentary, The Greatest Love Story Never Told.” The outlet alleged that JLo “might have referenced why Diddy broke up with her” when she “referenced her past relationships” in her documentary.
One of the more shocking parts of her documentary was JLo’s on-air confessional that she’d been mistreated in some of her previous relationships. She revealed, “There were people in my life who said, ‘I love you,’” but these lovers never acted in ways that “were kind of in line with the word, love.”
JLo also said she’d been “thrown around and mishandled” in past relationships, which wasn’t “fun.” Her bombshell was getting explosive.
Then, JLo claimed in her documentary that she was “never in a relationship when [she] got beat up, thank God.” No one deserves to get treated like that.
She alleged that she’d “definitely been manhandled, and a couple of other unsavory things.” JLo called it “rough” and “disrespectful,” but she never mentioned Diddy’s name directly.
JLo “Just Knew” Diddy Was Cheating
Stylecaster also mentioned something else that JLo told Vibe back in the day. This was after she claimed that she’d “never caught [Diddy] cheating, but [she] just knew.” Stylecaster wrote that JLo and Diddy “officially called it quits” after she thought about it long and hard, and JLo explained why.
She had to ask herself a crazy question: “Do I want to be home with kids in 10 years, wondering where somebody is at 3 in the morning?” Thankfully, her answer was no.
RELATED: Diddy’s Life In Prison
In March 2024, US Weekly reported on all of JLo’s “quotes about Diddy through the years.” This was bound to get juicy, especially when JLo revealed what it felt like getting arrested with Diddy in that getaway car.
JLo was interviewed by Elle magazine in July 2000, and she shockingly described the night of her arrest as a “complete nightmare from beginning to end.” She also confessed that she was “scared to death in the car.”
JLo claimed she had “absolutely no idea what was going on.” She added, “No one did.”
JLo Still Has Love for Diddy
US Weekly revealed that JLo and Diddy met “on the set of a music video” the year they started dating. Their relationship wasn’t just a rollercoaster behind the scenes. US Weekly wrote that JLo and Diddy “experienced some major highs and lows” together in public.
One of the most famous moments in JLo’s relationship with Diddy was the Grammy Awards in 2000. Diddy was JLo’s date that night when she wore that super-revealing “green Versace dress” that everyone still talks about today.
A decade ago, JLo was interviewed by Access Hollywood, and she dropped the craziest bombshell possible about Diddy. It’s crazy because JLo spoke fondly of her time with Diddy. You need to hear this.
She claimed that Diddy “gave [her] so many cues and taught [her] so many things.” Shockingly, JLo claimed she would “always be grateful” to Diddy, and she alleged, “There’s still so much mutual respect, admiration, and love there.”
