“The first time I was with someone who wasn’t faithful”: Jennifer Lopez Was Crying and Going Crazy in Her Relationship With Diddy Before Their Breakup

Emotional turmoil as Jennifer Lopez struggled with Diddy before their split was revealed.

"The first time I was with someone who wasn't faithful": Jennifer Lopez Was Crying and Going Crazy in Her Relationship With Diddy Before Their Breakup

SUMMARY

  • Jennifer Lopez and P. Diddy's unexpected encounter in 1999 sparked a high-profile romance.
  • Despite appearing happy in public, Lopez felt overwhelmed and emotionally drained by her relationship with Diddy.
  • Infidelity and emotional turmoil led to their breakup in 2001, despite Diddy's attempts to win Lopez back.
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In the late 1990s, everybody couldn’t get enough of Jennifer Lopez and Diddy’s relationship. It was all around the sensationalist newspapers and gossip sections. But, behind the flashy headlines was a story of heartbreak. Reports were popping up about the 54-year-old crying and feeling really stressed in her relationship with Diddy.

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Jennifer Lopez
Jennifer Lopez in This Is Me…Now

It appeared as though things were falling apart between them. Before they called it quits, Lopez’s emotional rollercoaster gave a peek at the intense side of popularity and fortune. Yet, we should rewind a bit and see where this entire saga started.

Jennifer Lopez And Diddy’s First Encounter Unfolded Unexpectedly

In 1999, everybody was going crazy about Jennifer Lopez and Diddy, as they were all in the news. J.Lo hit it huge with Selena in ’97, then, at that point, continued to kill with Out of Sight and Anaconda.

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Meanwhile, Diddy had already become a rap star, dropping his second solo album. Now, the pop sensation, and Diddy, the rebellious rapper, probably won’t have appeared as though they were a perfect pair, but they began dating that year.

Jennifer Lopez And Diddy
Jennifer Lopez and Diddy (credit: The Mother and Instagram: @diddy)

Both celebrities hail from the Bronx, which helped them connect. Before they started dating, they had previously run into each other in the music business, with J.Lo showing up in Diddy’s music video, Been Around the World, and later collaborating on her debut album.

According to Newsweek, they became closer while working on her video for If You Had My Love, sparking their romance. In the archived interview, Diddy claims it was love at first sight, but J.Lo wasn’t at first sold. She thought he wasn’t as family-oriented as she was. The actress said,

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“We developed this bond. We both understood where we were at that time in our lives and we both knew nobody else understood exactly how we felt.”

However, they became friends and found comfort in each other’s understanding of their crazy lives. Their bond bloomed into perhaps one of Hollywood’s most smoking feelings. But, in the same way as other Hollywood romantic tales, theirs didn’t have a fantasy finish.

Jennifer Lopez Felt Overwhelmed By Her Relationship With Diddy

Jennifer Lopez in Selena (1997)
Jennifer Lopez in Selena (1997)

Lopez has some intense memories of managing her relationship with Diddy. They looked cheerful on the red carpet, but behind the closed doors, it was disarray.

Lopez referred to that period as “crazy.” In a 2003 interview with Vibe magazine, Lopez revealed she was continually upset and felt like she was losing it while dating Diddy. She said,

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“The first time I was with someone who wasn’t faithful. I was in this relationship with Puff where I was totally crying, crazy and going nuts, it really took my whole life in a tailspin.”

As per Entertainment Weekly, there were times when Diddy would vanish, passing on Lopez to look for him in hotel rooms. Their relationship, however once talk of the town, crumbled under the tension. According to Newsweek, they called it quits in 2001, declaring their separation on Valentine’s Day. 

Infidelity was a significant issue, with Lopez thinking Diddy was cheating. Diddy later admitted he actually cared deeply about his ex, Kim Porter, on True Hollywood Story. He tried to win Lopez back with excellent gestures like sending her 100 white doves, yet it didn’t work ( as per Entertainment Weekly). This peek into Lopez’s emotional rollercoaster highlights the struggle for fame.

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Written by Muskan Chaudhary

Articles Published: 694

Muskan Chaudhary, Junior Content Writer at Fandom wire. Having completed her degree in Commerce, she has written over 500 articles spanning FandomWire and Animated Times in the pop culture. She is dedicated to bring the latest and informative content from the entertainment world, thus expanding her knowledge in the field. Apart from her contributions to FandamWire, she has a keen interest in video games, sketching and playing tennis.