The celebrity romance that went off with a bang. Welcome to MsMojo, and today we’re taking you back to when Diddy met JLo and the rollercoaster of a relationship that ensued.
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00:00At first, I didn't like him at all, you know? I didn't. I thought he was, like, you know, it."
00:08Welcome to Ms. Mojo, and today we're taking you back to when Diddy met J-Lo
00:12and the rollercoaster of a relationship that ensued.
00:15"...tough time and, you know, what can you do? You just gotta go through it."
00:22Part 1. If You Had My Love
00:24The year was 1999. Sean Diddy Combs was still going by Puff Daddy,
00:29with his second studio album Forever on the horizon.
00:32Jennifer Lopez, meanwhile, was better known as a dancer and actress. Two years earlier,
00:37Lopez appeared in Diddy's Been Around the World music video and starred in the biopic Selena.
00:42"'This turned out good. Susie did a good job."
00:47"'Yeah, I dig it. I like it if you like it.'"
00:50"'I like it. It looks good.'"
00:51Her portrayal of Selena Quintanilla-Perez marked a stepping stone to music,
00:55followed by the release of her debut album On the 6.
00:59In addition to serving as one of the album's producers,
01:02Diddy was featured on the track Feelin' So Good. He was also heavily involved in the music video
01:07for Lopez's lead single, If You Had My Love, suggesting a website theme as the dot-com bubble
01:13neared its peak.
01:14Rumors started circulating that Diddy was dating Lopez,
01:17whose marriage to Ohani Noah had recently ended.
01:20"'Cause they're always trying to make something of you and Puffy."
01:22"'Yeah, me and Puffy, me and Max Loma, tons of people. Me and Mark Anthony,
01:26who I did a duet with.'"
01:28Although Lopez initially told talk show hosts like David Letterman that Diddy was just a friend,
01:32their relationship became official following the MTV Video Music Awards
01:36for Best Actress in a Music Video.
01:39With Diddy becoming a music mogul and Lopez being a rising superstar,
01:43the courtship was bound to attract media attention.
01:46"'Things started to happen. I started looking into her eyes,
01:49more spending more time with her, and I just fell in love with her.'"
01:52Less than a year into the relationship,
01:55Diddy and Lopez were in the spotlight for more notorious reasons.
01:59On December 27, 1999, Diddy and Lopez were married.
02:04Part 2. I'll Be Missing You.
02:07On December 27, 1999, Diddy and Lopez were at a Times Square nightclub
02:12with Bad Boy Records artist Shine.
02:14"'At the club, they partied with a large entourage,
02:16including Bad Boy rapper Jamal Shine Barrow.'"
02:20"'They were in the VIP section. People were looking at them.
02:23Puffy was dancing. He had two bubblies in his hand.'"
02:26Diddy and Shine reportedly entered a confrontation with felon Matthew Scar Allen,
02:31all three drawing firearms.
02:33Gunshots were heard, with three bystanders being injured.
02:36Diddy, Shine, and Lopez were arrested,
02:39although the latter was quickly released without facing any charges.
02:42"'They say that we were evading police and I had a gun.'"
02:47"'Puffy was booked and held on gun possession charges, igniting a media frenzy.'"
02:52Diddy and Shine were both indicted, however.
02:54Despite the negative press,
02:56Lopez and Diddy managed to overshadow the shooting headlines
02:59with an iconic red carpet moment.
03:01The following February,
03:02the couple attended the 42nd Annual Grammy Awards.
03:05Diddy draped himself in a gray and white suit,
03:08but all eyes were on Lopez's green Versace dress.
03:11"'When Puffy showed up at the 2000 Grammys with Jennifer Lopez on his arm
03:15in a Versace dress that defied the laws of physics,
03:19it was the envy of men everywhere.'"
03:21Defined by its tropical pattern and deep neckline,
03:24the dress became instantly recognizable
03:26and a symbol of Lopez's coronation into the A-list.
03:31"'What are you talking about?'
03:32I said, oh, they just want me to come again to see what I'm gonna wear.'"
03:35Up until this point,
03:36some might have argued that Lopez was riding on the coattails of Diddy's success.
03:40Seeing Lopez slay the red carpet, though,
03:43she was the one making him look good.
03:45"'Has the trouble affected the relationship?'
03:50"'No.'"
03:51"'Okay.'"
03:52Whether intentional or not,
03:54their Grammys appearance sent a message.
03:56The gun trial isn't going to hold us down.
03:58That said, the charges were not going away.
04:01Diddy recalled being scared leading up to the trial's verdict in March 2001.
04:05"'It was a scary situation,
04:06because you had, you know, 12 people who hold the fate of your life.
04:13But, you know, I put it in God's hands,
04:15and, you know, he brought me out of it,
04:17and I give all glory to God, and I'm forever grateful.'"
04:19While Diddy was acquitted,
04:21Shine got the short end of the stick,
04:23serving almost a decade in prison.
04:25Since being released in 2009,
04:28Shine has returned to his birthplace of Belize,
04:30where he's become a political leader.
04:32"'Let us not lose sight of what the cold hard facts are.
04:36This was not someone who I vacationed with,
04:39and who he and I enjoyed this great intimate relationship of brotherhood.
04:46This is someone who destroyed my life.'"
04:48The gun trial essentially ended his friendship with Diddy,
04:51who was also down one girlfriend.
04:53A month before Diddy was cleared of all charges,
04:56his two-year relationship with Lopez ended.
04:59We'd be surprised if the shooting and trial
05:01didn't put a strain on the relationship.
05:03"'I, at that time, was, uh, cared very deeply, uh, for, for Shine,
05:11and, um, you know, we just, we just didn't have the same kind of ideals
05:16about life and family and stuff like that,
05:19and it just wasn't a good relationship for me.'"
05:22According to Lopez, though,
05:24infidelity was at the root of their breakup,
05:26saying it was, quote,
05:27"'the first time she was with someone who wasn't faithful.'"
05:30While Lopez didn't catch him cheating,
05:32she could sense what Diddy was up to every night he didn't return home.
05:36"'He felt like he loved me very much, and I know he did,
05:39and I, I felt like the same way,
05:40so if I was unhappy in some way,
05:43then I was the one who had to do something.
05:45Not him, he was doing everything he wanted to do.'"
05:47Lopez remembered crying and feeling she was, quote,
05:51conceding that Diddy would never fully commit.
05:54Diddy wasn't quite ready to give up on Lopez,
05:57sending her 100 white doves and 100 pink balloons.
06:00"'And they released, like, hundreds of doves, white doves.
06:05Oh my God, I can't breathe.
06:07Right, and I was like, oh, oh my God.
06:12Did it work? Did you go back with him?
06:14No, it didn't work.
06:15All right.'"
06:16He also asked singer Luther Vandross to serenade her,
06:19and had employees, quote,
06:20"'camp outside MTV's TRL studios with signs to win Lopez back.'"
06:25Lopez wasn't swayed, and both went their separate ways.
06:28Diddy got back together with his ex, Kimberly Porter, for a period.
06:32Lopez married backup dancer Chris Judd in September 2001,
06:36although they divorced in 2003.
06:38"'My last marriage made me very cautious to
06:43kind of fall in love with anybody, you know,
06:45and I know it may not seem like that to people,
06:48but too bad.'"
06:50Before her marriage ended,
06:51Lopez entered a relationship with Ben Affleck.
06:54Even as the Bennifer saga came to define her love life,
06:57Lopez received questions about Diddy.
07:00Lopez often described Diddy as a friend and mentor
07:03in interviews that admittedly played differently
07:05through a modern lens.
07:06"'He helped me a lot.
07:08He was kind of like a mentor in a way.
07:11Not a mentor, but like guided me.
07:13You know, he had a rough way of doing it,
07:16but he did guide me.'"
07:19Still, one can see how Diddy influenced
07:21Lopez's career and business instincts.
07:24Like Diddy, Lopez didn't stop with music,
07:26launching beauty and fashion lines.
07:28"'You've got a surprise for these guys.
07:30You're gonna let them try on clothes.'"
07:31"'I do, you know, I have my new clothing line.'"
07:34Lopez wasn't just an actress, dancer, or singer.
07:37She was a brand.
07:38Between Lopez's media ventures and new romances,
07:41her relationship with Diddy became an afterthought.
07:43Diddy still came up on occasion.
07:45In 2015, Wendy Williams asked Lopez
07:48if she would ever get back together with Diddy.
07:50"'I was telling you that I could always see you
07:54getting back with Puffy in a little way.'"
07:59Let's just say Lopez's mother did not approve.
08:01The two nonetheless seemed to be on good terms in 2018
08:04when Diddy attended Lopez's All I Have Vegas party.
08:08During the 2020 pandemic,
08:10Lopez and Diddy participated
08:12in an Instagram Live dance-a-thon charity.
08:16After Lopez rekindled her relationship with Affleck in 2021,
08:24Diddy seemingly threw shade
08:25with a throwback photo of himself and his ex on Instagram.
08:29After deleting the pic, Diddy stated,
08:31quote,
08:31"'I don't have nothing to say about her relationship or her life,'
08:35calling Lopez his," quote,
08:36"'friend.'"
08:37Although there seemed to be no ill will,
08:39Lopez's relationship with Diddy
08:41was put under a microscope again
08:42with the release of her 2024 documentary,
08:45The Greatest Love Story Never Told.
08:47In the doc, Lopez said she, quote,
08:50"'was never in a relationship where she got beat up,'
08:52but had,' quote,
08:53"'definitely been manhandled.'"
09:05While Lopez didn't name names,
09:06it was hard not to think of Diddy
09:08as he became the face of an abuse scandal.
09:13Shortly before Lopez's documentary dropped,
09:16Diddy faced a sexual assault lawsuit
09:18from his ex, Cassie Ventura.
09:20Though Cassie and Diddy did not detail
09:22the terms of that agreement,
09:23the settlement quickly shuts down
09:25the potential for a trial
09:26and the process of legal discovery.
09:28That's when evidence in the case is often made public.
09:32Despite settling out of court,
09:33footage of an altercation between Ventura and Diddy
09:36effectively destroyed the latter's image.
09:38The abuse claims and lawsuits
09:40didn't stop with Ventura either.
09:42More than 100 people have pursued legal action
09:44against the music mogul.
09:46The controversy has not only reshaped
09:48how the public views Diddy,
09:49but has also raised questions
09:51about those closest to him.
09:53Many now asking how the man
09:55who allegedly behaves so abusively
09:58was able to do it so often
10:01and for so long.
10:02Months before Diddy's arrest,
10:04Lopez and Affleck separated.
10:06Diddy's longtime rival
10:07and convicted felon, Suge Knight,
10:09theorized the FBI found compromising videos
10:11of Lopez during a home raid.
10:20Knight believes Lopez lied
10:22during the 1999 gun case,
10:24sparing Diddy from prison
10:25and selling out Shine.
10:27That is supposedly why Affleck
10:29wanted out of their marriage,
10:30although Knight provided no evidence
10:32backing up these accusations.
10:42Rodney Little Rod Jones
10:45has also claimed that Diddy
10:47used Lopez to smuggle the gun
10:48into the club.
10:50Amid Diddy's arrest,
10:51an old photo resurfaced
10:52depicting him in bed with Lopez,
10:54Aaliyah, and several others
10:56at a 2000 party.
10:57The context of the photo is unclear,
11:00but it epitomized a question
11:01on everyone's minds.
11:03How many people were in bed with Diddy?
11:05If the allegations about Diddy's
11:07infamous white parties
11:08and freak-offs are true,
11:09it'd take a village
11:10to keep a secret like this under wraps.
11:19Lopez has remained quiet thus far,
11:21although an insider says
11:23she's, quote,
11:23horrified by all of the accusations
11:25against Diddy.
11:26The unnamed source added, quote,
11:28She and Diddy had talked about marriage
11:30at one point,
11:31but she left him for a reason.
11:33We're two human beings.
11:34It's not like I'm walking around
11:36the house, I'm a bad boy,
11:37and she's like, good girl.
11:38I mean, she has a little bit of age
11:39for her also.
11:40Now people want to know why
11:42and what she saw.
11:43We still don't know what Lopez
11:44might have seen during those two years.
11:46According to the insider, though,
11:48quote,
11:49There were many wild moments with Diddy.
11:51Lopez was apparently afraid
11:53to leave Diddy,
11:54receiving death threats,
11:55and is creeped out that she stayed
11:57with him for so long.
11:58The cameras are going, okay?
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12:18As highly publicized
12:19as their relationship was,
12:21many questions about Diddy and J-Lo
12:22remain unanswered.
12:24So that's the way it was
12:24with you and puppy?
12:26Um, it wasn't like that.
12:29Was Lopez a victim of Diddy's
12:31alleged abuse?
12:32Did she witness him inflicting abuse
12:34towards others?
12:35Was Lopez aware of the sex trafficking
12:37and racketeering
12:38that supposedly took place?
12:39We may never know,
12:41unless Lopez is called to testify
12:43at Diddy's trial.
12:44I think that's what we avoid
12:45a lot of times because
12:48it's usually the truth
12:50and the truth kind of
12:52is hard to deal with
12:53most of the time.
12:54For now,
12:55the early 2000s seemed like
12:57a simpler time
12:57when he was Puff Daddy,
12:59she was Jenny from the Block,
13:00and the discharge of firearms
13:02was as shocking
13:03as celebrity scandals got.
13:04When it's all over,
13:06whenever that is,
13:08whatever happens,
13:09it'll be a very happy day
13:11once it's
13:15not something
13:15we have to think about.
13:16What do you make
13:17of Diddy and J-Lo's relationship?
13:19Let us know in the comments.
13:21We had this kind of crazy,
13:22tumultuous relationship
13:25that ended in like a bang.
13:27Let's say.