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Jimmy Kimmel asks Diddy a wild question about Jennifer Lopez in chilling video: "You were gonna beat..."

Diddy and Jennifer Lopez had a highly publicized relationship from 1999 to 2001, after meeting on the set of 'If You Had My Love'

During one of the most bizarre moments on 'Jimmy Kimmel Live!', Sean "Diddy" Combs was left speechless when the conversation veered off from promoting his album, 'The Love Album', to an old, over-20-year-old rumor involving his ex, Jennifer Lopez. The rumor claimed that Will and Jada Pinkett Smith had allegedly propositioned J.Lo for a threesome, leaving Diddy reportedly furious and wanting to fight Will Smith over the situation.

During the October 30, 2024 episode, Kimmel wasted no time bringing up the rumor during their conversation about the new music. “Speaking of love,” he began, “I saw a guy on the internet the other day. He said he used to be your security guard, who said that when you were dating J.Lo, Will Smith and Jada tried to pick her up on a threesome and you were gonna beat up Will Smith. Is that true?” The question left Diddy speechless immediately. He was silent for a few seconds, clearly trying to process the question before answering. “Yo, this show has gotten crazier since the last time I was here. No,” Diddy said, obviously perplexed. After another very long pause, he simply said, “No,” to flatly deny the rumor.

Kimmel, seemingly unfazed by the awkwardness, replied, “It’s all about love though. That’s not true?” making it even more confusing. “You really heard that?" Diddy asked, clearly stunned by how the conversation had taken such a strange turn. Kimmel, as he normally does, responded in a deadpan, “Yeah, yeah, I watched it on the internet,” adding humorously, “You’re telling me I can’t believe everything I read?” At this point, Diddy was visibly uncomfortable. “I don’t know what you’re talking about,” Diddy said, shaking his head. “Jimmy, I thought we was friends. Where did this interview just go?”

Diddy and J.Lo had a highly publicized relationship from 1999 to 2001, after meeting on the set of Lopez’s music video for 'If You Had My Love'. However, their relationship ended when Diddy cheated on Lopez, as per Cheat Sheet. However, on her Facebook Watch show ‘Red Table Talk’, Jada Pinkett Smith candidly revealed to the world that she had a threesome back in her early 20s. However, she explained that, while she had tried it, she didn’t enjoy the experience due to the lack of intimacy.

“I had a threesome once. I was very, very young,” she said, as per Entertainment Online. “Like, early 20s.” Giving the details in front of her 18-year-old daughter, Willow, she added, “I didn't like it. It just didn’t have the level of intimacy. But I tried it once and I was like, ‘Well, that’s not for me.’ But I would think if I was in love with two people, that’s another level.” She further added, “I could see enjoying a threesome then, but I was a kid,” continuing, “I was just like, you know, I saw two cute people.” Despite admitting to having a threesome, Jada and Will Smith have continually denied rumors of having an open marriage, according to Cosmopolitan. The two claim their relationship involves “transparency”, implying they are candid with each other.