The instant Sean "Diddy" Combs and J.Lo descended upon the red carpet at the 2000 Grammys, the world
was forever changed. While J.Lo's green Versace dress stole the show, the couple's then-fresh
relationship was more of a mystery. Here's why Diddy and Jennifer Lopez couldn't make it work.
In 1999, Sean "Diddy" Combs and Jennifer Lopez started dating,
and they would be the first to admit that period of time was eventful.
On a 2019 episode of CBS Sunday Morning, Lopez said of the relationship,
"We had this kind of crazy, tumultuous relationship that ended in, like,
a bang, let's say."
This was reminiscent of her 2003 interview with Vibe, when Lopez revealed,
"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, as she told CBS Sunday Morning,
"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."
After less than two years together, the 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. [...] Mr. Combs is confirming this today, as he wanted to put all the rumors surrounding
their relationship to rest. At this difficult time, we ask that you respect his privacy."
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, he was acquitted.
It was in the middle of the trial that Diddy announced he and Lopez were no more.
Diddy told Access Hollywood that the trial was not easy on his and Lopez's relationship. He revealed,
"It was a rough year and I just want her to be happy [...] 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, Lopez also opened up about the difficult time and explained,
“It was a stressful year [...] I had come off three movies, then to make an album.
To deal with everything and the trial. It was extremely painful and draining,
but I’m sure not half as much as it was for him. I was always worried and preoccupied."
Though it put a strain on their romance, it did not cause their split. In 2002, Lopez told
Oprah Winfrey the nightclub incident was not to blame for her split from Diddy. She clarified,
"No, we were together for a year after that."
"It was a hard time."
Another thing working against this particular pairing? Jennifer Lopez
had a hunch Diddy was cheating on her. Speaking with Vibe in 2003, she claimed,
"It was the first time I was with someone who wasn’t faithful [...] 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."
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 of infidelity. And following his own split from Lopez, Marc Anthony told ABC
News in 2011 that the stories alleging he was unfaithful to J.Lo were untrue.
Plus, during a 2003 appearance on The Tonight Show with Jay Leno, Lopez's then-fiancé Ben
Affleck shut down tabloid reports that claimed acts of infidelity happened at his bachelor party.
"The whole thing was heartbreaking."
While the world found out that Lopez and Diddy had split in February 2001,
apparently that was not the first time they'd called things off. Lopez told Vibe in 2003 that
she and Diddy broke up and got back together a bunch of times over the course of their courtship.
In a Rolling Stone interview that evidently was conducted before their split,
the "Waiting for Tonight" singer said 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?'"
However, the former couple seems to have put all of the drama behind them now,
as Lopez 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 of unwinding. 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 said she worried about how
these late-night outings could impact their relationship down the line, and told Vibe,
"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 have lined up,
but they found common ground in 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."
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 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,
"It is hard being a celebrity in a relationship."
In a Vanity Fair story about Lopez, Diddy also recalled,
"We'd always say to each other that I was Frank [Sinatra] and she was Ava [Gardner],
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.
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. After that, Diddy and Lopez became an item. In a 2009 interview with Essence, Diddy
admitted he was trying to get Porter's attention when he started seeing Lopez. He told the outlet,
"Jennifer was my perfect match in terms of energy [...] I thought,
‘I’ll test the waters and hopefully Kim will see I’m serious and come running after me.'"
However, when Porter didn't come running back to Diddy, he was confused, and told Essence,
"So I was back at the house, trying to figure out what the hell was going on."
However, Porter was well aware that Diddy was still into her,
even while he was dating Lopez, and told the publication,
"He was calling fifty, sixty times a day. 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----. Like, this is not going down."
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 revealed on a 2013 episode of Oprah: Where Are They Now?,
it was the moment the world got introduced 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 the two wed in September the same year. A source later
suggested that Diddy's refusal to accept that his relationship with Lopez was over for good
might have pushed the singer to walk down the aisle with someone else. The source told People,
"I think she needed to get away from Puffy,
and [Judd] was great solid grounding for her [...] I think she got married as a way to say,
‘Let me go.' [...] I think it was Puffy’s refusal to accept things that drove her to [Judd]."
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 just a regular guy to someone whose
name was splashed across magazine covers. Of the experience, he told Us Weekly in 2014,
"You know it's very tough [...] Your privacy is breached. You're no longer a normal person.
[Our wedding] was a circus. I think several people got arrested trying to climb up a
mountain [...] trying to sneak in. We actually rented the airspace."
After more than 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. She noted that she does not
blame her former significant others for the way things went. J.Lo explained,
"For me, the relationship journey has been very up and down. But 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.
Once you do that, you can have relationships that are based on love and respect."
That same year, Lopez told People that she ended up in some relationships
because she had a fear of being alone. The superstar explained,
"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."
Even though their romantic relationship didn't work out, all is not lost,
as Jennifer Lopez and Sean Combs seem to be better off as friends.
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 post-split. Consider the 2015 American
Music Awards, where Diddy gave J.Lo a shout-out following her performance and then hung out with
her afterwards. Diddy also 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.
Per People, 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.
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