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.

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."

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." 

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?

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.

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.