Why Diddy And Jennifer Lopez Couldn't Make It Work

The instant Sean "Diddy/P. Diddy/Puff Daddy/Puffy" Combs and Jennifer Lopez descended upon the red carpet at the 2000 Grammys, the world was forever changed. Diddy and J.Lo, who were dating at the time, attended the music awards show together that year, and under most circumstances, their relationship would have been the only thing anyone wanted to talk about. But Lopez did something that evening that ripped the spotlight off of their personal lives for a short while: she wore that green Versace dress.

That gown, with its sheer silk chiffon and plummeting neckline, made fashion history and tech history. Internet dwellers wanted photos of Lopez in the garment, and the high demand ended up an impetus for the creation of Google Image. In a 2015 essay for Project Syndicate, former Google CEO Eric Schmidt wrote, "At the time, it was the most popular search query we had ever seen. But we had no surefire way of getting users exactly what they wanted: J­Lo wearing that dress. Google Image Search was born." Diddy told Entertainment Tonight in 2017 that he had a feeling the dress was going to be a moment, but "didn't know how big it was gonna be." 

...Wow, would you look at that? We wanted to revisit Diddy and Lopez's relationship, but ended up talking about what Lopez wore to the Grammys two decades ago. The dress strikes again! Let's start over: Superstar multi-hyphenates J.Lo and Diddy dated for a while, but things didn't work out. Here's what happened.

In 1999, Sean "Diddy" Combs and Jennifer Lopez started dating, and they would be the first to admit that period of time was, uh, eventful. On a 2019 episode of CBS Sunday Morning, Lopez called her years with Diddy a "kind of crazy, tumultuous relationship that ended in, like, a bang, let's say." This was reminiscent of what she said about their romance in a 2003 interview with Vibe: "I was in this relationship with Puff where I was totally crying, crazy and going nuts, and it really took my life in a whole tailspin."

Regardless, Lopez does not regret their years together. In the aforementioned CBS Sunday Morning interview, she said she believes her relationship with Diddy "was necessary." She continued, "He was meant to be in my life at that moment to teach me what I needed to know about the music business, about what kind of artist I wanted to be in the music industry."

After under two years, the piping hot A-list couple cooled off — and Diddy made the announcement on Valentine's Day 2001. According to ABC News, his publicist stated, "Mr. Combs confirmed that he and his love, Jennifer Lopez, have, in fact, broken up." The statement went on to say that Diddy "wanted to put all the rumors surrounding their relationship to rest." The Puffy and J.Lo era was officially done. 

About six months into their relationship, Diddy and Jennifer Lopez ended up in some legal trouble. In December 1999, they were arrested after fleeing a nightclub in Manhattan where a triple shooting occurred. Lopez's charges were dropped, but Diddy's were not. He went on trial for bribery and gun possession in January 2001, and as ABC News reported that March, he was acquitted. It was in the middle of the trial that Diddy announced he and Lopez were no more.

Diddy told Access Hollywood (via the Daily Mail) at the time that the trial was not easy on his and Lopez's relationship. "It was a rough year and I just want her to be happy," he said. The "Can't Nobody Hold Me Down" rapper also shared that he regretted going out that night, saying, "I had a better party at home than I could get anywhere else. I should have just stayed in with her."

In an interview with Vanity Fair that August, Lopez called the trial "extremely painful and draining," adding, "But I'm sure not half as much as it was for him." Though it put a strain on their romance, it did not cause their split. In 2002, Lopez told Oprah Winfrey that her and Diddy's breakup was "gradual," noting that the nightclub incident was not to blame for the dissolution of their relationship: "No, we were together for a year after that."

Another thing working against this particular pairing? Jennifer Lopez had a hunch Diddy was cheating on her. Speaking with Vibe (via Entertainment Weekly) in 2003, she claimed, "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." J.Lo told the publication that her relationship with Diddy "was the first time [she] was with someone who wasn't faithful." When Vibe asked about reports claiming she would go from hotel room to hotel room searching for him, Lopez said, "I can't remember right now, but I won't say it didn't happen." 

This would not be the last of Lopez's relationships to be hit with affair rumors. In 2016, a source claimed to People that Lopez broke things off with Casper Smart "because he cheated on her and he got caught." Following his split from Lopez, Marc Anthony told ABC News in 2011 that the stories alleging he was unfaithful were "absolutely not" true. During a 2003 appearance of The Tonight Show with Jay Leno, Lopez's then-fiancé Ben Affleck shut down the tabloid reports that claimed acts of infidelity happened at his impromptu bachelor party. 

And more recently, José Canseco claimed Alex Rodriguez cheated on Lopez with his ex-wife, Jessica Canseco, in 2019. While Jessica denied the accusation on Twitter, Lopez talked about it on The Breakfast Club: "I mean, it doesn't matter, I know what the truth is. I know who [Rodriguez] is." J.Lo will not be bested by gossip.

The world found out they split once and for all in February 2001, but apparently, that was not the first time Jennifer Lopez and Diddy called things off. Lopez told Vibe in 2003 (via Entertainment Weekly) that she and Diddy broke up and got back together a bunch of times over the course of their courtship, sharing (via British Vogue) that they split up so often that Diddy "didn't believe it was over when it finally ended." When it did end, that was that: On Valentine's Day 2001, Diddy's rep unleashed the scoop to ABC News that he and J.Lo were no more. 

In a Rolling Stone interview that evidently was conducted before their split, the "Waiting for Tonight" singer said her relationship with Diddy was "a lot," but good. Lopez went on to share that even though they did not see any wedding bells in their future, that did not stop Diddy from throwing around the d-word. She explained, "He's said to me many times, 'I want a divorce.' I'll be away so much, or he'll be ... he can't get away, whatever, but he'll say, 'So, where do I send the papers?'" 

All of these ups and downs and "divorce" requests happened, as Lopez said on The Breakfast Club in 2019, "such a long time ago," that they are doing the opposite of holding grudges. As she told E! News in 2014, "We always root for each other, we always support each other." 

While they had a common interest in making music, when it came time to relax, Jennifer Lopez and Diddy had very different ways to unwind. She told Rolling Stone in 2001, "He's been a going-out-to-clubs person all his life, doing his thing. I've always been a homebody. So we switch off what we do when we're together." A couple years after they broke up, J.Lo expressed to Vibe (via Entertainment Weekly) that she worried about how these late-night outings could impact their relationship down the line: "I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?"

Lopez and Diddy's ideas of how to spend their downtime may not totally line up, but the same cannot be said about the way they go about their professional lives. In her Behind the Music episode, Lopez said of the rap mogul: "We were both very ambitious and both kind of had the same ideas about our careers. We loved working and wanted to do great things." And when the subject of work ethic and drive came up during her 2019 appearance on The Breakfast Club, she agreed when Charlamagne tha God called Diddy "a hell of a hustler." 

From 1999 to 2000, you could not stand in a grocery store checkout line, flip on an episode of Entertainment Tonight, or log into America Online without seeing at least one story about Jennifer Lopez and Sean "Puffy" Combs' relationship. The duo of Diddy and J.Lo was huge, and their drama was a fixture of the tabloids. Evidently, all of the attention and the spotlight took a toll on them. Diddy said it best in a 2001 interview with Access Hollywood (via the Daily Mail): "It is hard being a celebrity in a relationship."

In a Vanity Fair story about Lopez that August, Diddy recalled, "We'd always say to each other that I was Frank and she was Ava, you know what I'm saying? Everything always being up and down. Or Joe DiMaggio and Marilyn Monroe." Considering all of the publicity Lopez and Diddy got during their time together, it is not terribly shocking that they related to two incredibly famous couples who also happened to receive a lot of media attention. It is also pretty telling (and sort of grim?) that they connected with two infamously tumultuous romantic pairings. But hey, who knows J.Lo and Diddy's story better than J.Lo and Diddy do?

Before and after he was with Jennifer Lopez, Diddy was with the late Kim Porter. Over the course of their 13-year on-again, off-again courtship, Diddy and Porter had three children together, and Diddy adopted the model's son from a previous relationship. The two began dating in 1994, and as the New York Post reported in 2001, Diddy and Porter had their first very public split five years later. Then, Diddy and Lopez became an item.

In a 2009 interview with Essence, Diddy admitted he was "making a statement" when he started seeing Lopez. He told the outlet: "I thought, 'I'll test the waters and hopefully Kim will see I'm serious and come running after me.'" When Porter did not come running after him, he said he was "back at the house, trying to figure out what the hell was going on."

Porter told the publication that Diddy was "still in love" with her and would call her "fifty, sixty times a day." She recalled, "Sometimes I wouldn't even talk to him because I was so angry. I couldn't be 'nice Kim.' I had to be, you know, that b**ch. Like, this is not going down." During an episode of E! True Hollywood Story, Diddy admitted that he "was still in love with Kim" when he was dating Lopez. Porter and Diddy got back together in 2003 and broke up in 2007. 

When giving a eulogy at her funeral in 2018, Diddy called Porter "irreplaceable."

In late 2000, Jennifer Lopez met dancer Cris Judd on the set of the music video for "Love Don't Cost a Thing." A handful of weeks after Diddy announced his and J.Lo's breakup, Lopez rebounded and brought Judd to the 73rd Academy Awards. This was a major moment for the two. As Judd said on a 2013 episode of Oprah: Where Are They Now?, it was the world's "first introduction" to J.Lo's new boyfriend. 

A few months after they walked the red carpet at the 2001 Oscars together, Judd proposed to Lopez. She accepted, and as People reported, the two wed in September of that year. A source later cited by the outlet claimed that "Puffy's refusal to accept" his and Lopez's breakup supposedly influenced her decision to walk down the aisle with Judd on some level, alleging, "I think she got married as a way to say, 'Let me go.'" Lopez and Judd split up in July 2002, and their divorce was made official the next year. 

In a span of only a few months, Judd went from being, as he put it in a 2014 interview with Us Weekly, "a normal person" to someone whose name was splashed across magazine covers. He told the magazine that being thrust into the limelight so suddenly was "tough," but "had no bearing on the outcome" of his and Lopez's marriage. "Unfortunately, it just didn't work out," Judd said. Well, you won't know if marrying one of the most famous people on the planet will work until you try.

After over two years of dating, Jennifer Lopez and baseball legend Alex Rodriguez announced in March 2019 that they were engaged. A lot has been made of J.Lo's past relationships, including ample speculation about why they did not work out, but she has moved on and continues to move forward. 

When speaking to Harper's Bazaar in 2019, Lopez opened up about what she believed went wrong with her previous romances. Admitting that the "journey has been very up and down," she noted that she does not blame her former significant others for the way things went. J.Lo explained, "It didn't have to do with anybody else but me — it was about me figuring out me. Until you learn to love yourself, you can't completely love [someone else] in a way that is pure and true." Lopez said a personal "evolution had to happen," adding, "I feel like I'm in a better place now."

That same year, Lopez told People that she ended up in some relationships "for the wrong reasons" because she "didn't like being alone," but added that "now that [fear] is gone." She shared, "When I really figured out you don't need anybody to complete you and you can be happy on your own, the shift happened (and) all of sudden I wasn't alone. You do actually find that person." We should all strive to J.Gro like J.Lo. 

Things did not pan out for them as far as being in a romantic relationship was concerned, but all is not lost: Jennifer Lopez and Sean Combs seem to be better off as buddies. As Diddy said during a 2016 appearance on The Breakfast Club, "Me and Jennifer, we gotta, people gonna be friends, man. People gonna grow, and, you know, any of my exes, they smile and they're happy to see me." 

These celeb exes really do seem to be in a good place all these years later. Consider the 2015 American Music Awards, where Diddy gave J.Lo a shout-out following her performance and then hung out with her at her after party. Or how about the time when Diddy attended Lopez's final Las Vegas residency show in 2018, where she gave him a shout-out during the performance before the two hung out once again at the after party.

Diddy and Lopez reunited again in April 2020 via Instagram Live for a quarantine dance party. As People reported, Diddy hosted a dance-a-thon on the social media platform to raise money for a nonprofit called Direct Relief. For one part of the virtual event, Lopez and her fiancé, Alex Rodriguez, joined Combs and his kids — and there was a lot of dancing and laughing and love. Over 22 years after they appeared in the "Been Around the World" music video, they danced together on Instagram Live. J.Lo and Diddy really do have a bond like no other pair of exes.