<p id=”par-1_39″><a href=”https://www.cheatsheet.com/tag/jennifer-lopez/”>Jennifer Lopez</a>’s relationship with Sean ‘Diddy’ Combs lasted for two years before <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-shared-knew-sean-diddy-combs-unfaithful.html/”>the pair called it quits</a>. But after they reunited backstage at an awards ceremony, Diddy’s girlfriend at the time, Cassie, couldn’t help but inquire about the meeting.</p>
<h2 class=”wp-block-heading” id=”h-sean-diddy-combs-was-caught-reuniting-with-jennifer-lopez-at-an-awards-show”>Sean ‘Diddy’ Combs was caught reuniting with Jennifer Lopez at an Awards show</h2>
<figure class=”wp-block-image size-full” id=”emb-1″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2024/09/Jennifer-Lopez-Diddy.webp?strip=all&quality=80″ alt=”Sean ‘Diddy’ Combs and Jennifer Lopez stand together. He wears a black suit jacket and sunglasses. She wears a black dress.” class=”wp-image-3708739″><figcaption class=”wp-element-caption”>Sean ‘Diddy’ Combs and Jennifer Lopez | Stephane Cardinale/Sygma via Getty Images</figcaption></figure>
<p id=”par-2_67″>Lopez and Diddy’s relationship didn’t last long. Although the two celebrities fell hard for each other, their lifestyles weren’t compatible in the end. The “Jenny on the Block” singer has been candid about how being Diddy was a stressful period in her life that <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-cried-surprise-birthday-party-sean-p-diddy-combs-threw.html/”>left her crying</a> on a few occasions. As instantaneous as their bond was, Lopez knew deep down their relationship wasn’t built to last.</p>
<p id=”par-3_50″>“He was like, ‘I love you’. Right away. It was very fast, but we did have a connection,” Lopez once said on VH1’s <em>Behind the Music</em> (via <a href=”https://1053rnb.com/410871/video-j-lo-exposes-diddy-on-vh1-the-relationship-did-get-ugly/”>105.3</a>). <em>“</em>We did fall in love and we were very close. But my relationship with him was always something I knew would end.”</p>
<p id=”par-4_61″>Lopez’s prediction would come true, as she and Diddy would go their separate ways for good in 2001 after <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-called-1-night-sean-diddy-combs-complete-nightmare.html/”>a chaotic relationship</a> full of scandals. Both would eventually move on with other life partners, but she and Lopez would still maintain contact over the years. And at the time, they didn’t mind catching up with each other when they crossed paths.</p>
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<iframe title=”Diddy introduces Ryan Leslie & Cassie to Warner/Atlantic on March 9, 2006″ width=”925″ height=”694″ src=”https://www.youtube.com/embed/B1zqmcpP62g?feature=oembed” frameborder=”0″ allow=”accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share” referrerpolicy=”strict-origin-when-cross-origin” allowfullscreen></iframe>
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<p id=”par-5_48″>The two were once photographed hanging out backstage at the 2015 American Music Awards. The incident was brought up during Diddy’s interview with <em><a href=”https://www.youtube.com/watch?v=BsA7wpWgFZQ&ab_channel=BreakfastClubPower105.1FM”>The Breakfast Club</a></em> because of <a href=”https://www.cheatsheet.com/entertainment/sean-diddy-combs-felt-god-sent-cassie-save-bad-boy-records.html/”>his relationship with Cassie</a> back then. The CEO maintained that Cassie didn’t mind him being so chummy with his ex.</p>
<p id=”par-6_19″>“My woman, at the end of the day, you know, she ain’t have a problem with it,” Diddy said.</p>
<p id=”par-7_29″>Still, he joked that Cassie might’ve had a few suspicions back then. But whatever concerns she had were quelled by the fact that Lopez was in <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopezs-famous-exes-a-look-back-at-the-stars-love-life.html/”>her own relationship</a>.</p>
<p id=”par-8_59″>“She had some questions,” he said. “She had some questions but not, not…you know, Casper was there. Me and Jennifer, people gonna be friends, man, people gonna grow, and, any of my exes, they smile and they’re happy to see me, and that’s all that was about. And, you know, I answered the question and we kept it moving.”</p>
<h2 class=”wp-block-heading” id=”h-sean-diddy-combs-still-considered-jennifer-lopez-his-girl-long-after-they-broke-up”>Sean ‘Diddy’ Combs still considered Jennifer Lopez his girl long after they broke up</h2>
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<p id=”par-9_49″>Lopez’s connection with Diddy was immediate and powerful when they met on the set of her music video “If You Had My Love.” The two would end up dating later that year, but started off more as friends and business partners. They quickly bonded over their ambition and upbringing.</p>
<p id=”par-10_51″>“Puffy and I both <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-visit-bronx.html/”>grew up in the Bronx</a>. He had been in the music business and had all this success. I was just starting and making my first album when I met him. He became kind of a mentor to me in that moment,” Lopez said on <a href=”https://www.cbsnews.com/video/jennifer-lopez-on-relationships-and-tabloids-in-the-bennifer-era/”>CBS Sunday Mornings</a>.</p>
<p id=”par-11_30″>Diddy would help Lopez develop her debut album “On the 6.” While working alongside her, Lopez’s longtime manager Benny Medina theorized he was attracted to Lopez’s talents and star potential.</p>
<p id=”par-12_31″>“Puffy is the type of manager/producer/artist/entrepreneur who could very well see her potential, and I think he fell in love with that as much as he did her,” Medina told <a href=”https://www.billboard.com/music/pop/jennifer-lopez-on-the-6-if-you-had-my-love-interview-8513788/”>Billboard</a>.</p>
<p id=”par-13_17″>But Lopez’s relationship came as a shock considering she was adamant about not dating the music mogul.</p>
<p id=”par-14_56″>“Which was funny, because at the beginning of the album, not only was he not her boyfriend, but she wasn’t even interested. At all,” her producer Corey Rooney remembered. “She was like ‘oh my god please, he doesn’t have a shot.’ You know, but after a few cheat codes he was given, he figured it out.’</p>
<p id=”par-15_30″>Their friendship wasn’t something Diddy was willing to let go. Even after Lopez was officially off the market <a href=”https://www.cheatsheet.com/entertainment/marc-anthony-said-jennifer-lopez-stand-enjoy-life-little.html/”>by marrying Marc Anthony,</a> he still felt connected to the <em>Hustler</em>s star.</p>
<p id=”par-16_25″>“If she’s in love with somebody and that makes her happy, I’m happy for her,” Diddy once told the <a href=”https://www.heraldtribune.com/story/news/2004/06/07/affleck-and-p-diddy-react-to-jlos-surprise-weekend-marriage/28809502007/”>Herald-Tribune</a>.” That’s my girl for life.”</p>