Sean ‘Diddy’ Combs Felt Dating This Unknown Actor Would’ve Been Like Dating J.Lo Part 2

5 hours ago

<p id=”par-1_39″><a href=”https://www.cheatsheet.com/tag/sean-diddy-combs/”>Sean ‘Diddy’ Combs</a>’ relationship <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-shared-relationship-sean-diddy-combs-worked-well.html/”>with Jennifer Lopez</a> was full of scandal and controversy back in the day. But if he had gone through dating this other actor, Diddy felt sure it would’ve been like dating Lopez all over again.</p>

<h2 class=”wp-block-heading” id=”h-sean-diddy-combs-recalled-trying-to-date-this-a-list-actor”>Sean ‘Diddy’ Combs recalled trying to date this A-List actor</h2>

<figure class=”wp-block-image size-full” id=”emb-1″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2024/10/Jennifer-Lopez-Diddy-1.webp?strip=all&quality=80″ alt=”Jennifer Lopez and Sean ‘Diddy’ Combs” class=”wp-image-3723863″><figcaption class=”wp-element-caption”>Jennifer Lopez and Sean ‘Diddy’ Combs | Kevin Mazur Archive 1/WireImage</figcaption></figure>

<p id=”par-2_51″>Diddy’s relationship with Lopez took a turn for the worst not too long after they started dating. The pair were first linked together in 1999. That year alone saw Lopez involved in the now <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-called-1-night-sean-diddy-combs-complete-nightmare.html/”>infamous NYC nightclub shooting</a>, where Diddy allegedly got into an altercation that led to guns being drawn.</p>

<p id=”par-3_48″>Still, despite the controversies, Lopez remained with Diddy on and off for two years before their relationship ended for good in 2001. After a while, the “On the Floor” singer simply couldn’t imagine spending the rest of her life with Diddy and all of the chaos surrounding him.</p>

<p id=”par-4_44″>”It was the first time I was with someone who wasn’t faithful,” Lopeze once told <em>Vibe </em>(via <a href=”https://ew.com/article/2003/05/26/j-lo-finally-dishes-p-diddy/”>Entertainment Weekly</a>). ”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.”</p>

<p id=”par-5_30″>”I never caught him <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-shared-knew-sean-diddy-combs-unfaithful.html/”>but I just knew</a>. He’d say he was going to a club for a couple of hours and then never come back that night,” Lopez added.</p>

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<p id=”par-6_56″>But it seemed Diddy was on his way to repeating his tumultuous relationship with Lopez with another actor. The music mogul wouldn’t reveal his mysterious partner’s name. However, it was clear she was a big deal with how aggressively he pursued her. He described it as a pairing that would’ve shocked everyone had it gone pubic.</p>

<p id=”par-7_99″>“There was a young lady who’s an actress,” Diddy once told <a href=”https://www.huffpost.com/entry/diddy-i-tried-to-lose-my_n_394970″>HuffPost</a>. “She’s famous. I liked her, so I was willing to do whatever I had to do… We started spending time together, but we were prisoners of our celebrity. She took me out to dinner after we got to know each other and hit me with a line that was straight out of the movies. She said, ‘You know this will never work, right?’ I knew she was right…This was going to shake up the world. It would have been a Puff and J. Lo situation, part two.”</p>

<p id=”par-8_26″>Whoever this actor was, she might have dodged a bullet. Today, she could’ve been one of several celebrities caught up in the <a href=”https://www.cheatsheet.com/entertainment/sean-diddy-combs-trial-date-likely-pushed-may-2025.html/”>music mogul’s current scandals</a>.</p>

<h2 class=”wp-block-heading” id=”h-fans-accused-sean-diddy-combs-of-trolling-jennifer-lopez-s-relationship-with-ben-affleck”>Fans accused Sean ‘Diddy’ Combs of Trolling Jennifer Lopez’s relationship with Ben Affleck</h2>

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<p id=”par-9_48″>Diddy wasn’t going to give up on Lopez easily even after she ended things. In an interview with<em> Variety </em>(via <a href=”https://ew.com/article/2001/05/10/puffy-tells-all-about-his-failed-romance-j-lo/”>Entertainment Weekly</a>), Diddy claimed he tried wooing Lopez back with several grand gestures. This included having singer Luther Vandross singing for Lopez, and sending her 100 white doves.</p>

<p id=”par-10_45″>Lopez corroborated Diddy’s white doves story in an interview on <em><a href=”https://www.youtube.com/watch?v=FbvACEJKLl8&ab_channel=starstracks29″>The Wendy Williams Show</a></em>. However, she wouldn’t say that the gesture was from Diddy. She claimed she was getting ready for an event at the time when her unnamed ex sprang the surprise on her.</p>

<p id=”par-11_30″>“So, I go to the window. The person who was in charge out there saw me appear at the window. And they release hundreds of doves. White doves,” Lopez recalled.</p>

<p id=”par-12_57″>The two remained friends for a long time after their breakup. Diddy would even comment on some of Lopez’s later lovers. On his social media, Diddy released a throwback picture of her and Lopez right after she and Affleck <a href=”https://www.cheatsheet.com/entertainment/jennifer-lopez-wouldnt-suggest-getting-ex-reuniting-ben-affleck.html/”>reignited their relationship</a>. Some felt Diddy was “trolling” with the timing. But Diddy clarified that wasn’t the case.</p>

<p id=”par-13_27″>“It wasn’t no trolling involved,” Diddy said to <a href=”https://www.vanityfair.com/style/2021/08/from-puff-daddy-to-diddy-to-love”>Vanity Fair</a>. “That’s just my friend. And I don’t have nothing to say about her relationship or her life.”</p>