Diddy Sent Bad Boy Staff to Stand Outside ‘TRL’ Studios With Signs to Win J. Lo Back

Sean “Diddy” Combs and Jennifer Lopez split in 2001 after rumors of infidelity began swirling. However, a new report claims that Combs wasn’t ready to walk away from the relationship.

Combs, 54, had Bad Boy Entertainment staff members stand outside of the ​Total Request Live (TRL) studio in 2001 when Lopez, 51, appeared on the MTV show alongside her Wedding Planner costar Matthew McConaughey. In the crowd outside, the Bad Boy employees held signs for Combs as a ploy to win Lopez back, according to a report from Rolling Stone.

Lopez and Combs began dating in 1999 after meeting on the set of Lopez’s music video for “If You Had My Love.” He famously accompanied the Maid in Manhattan star to Grammy Awards in 2000, but by 2001, things had soured between the couple and they went their separate ways. In 2003, Lopez opened up about their split to Vibe.

“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,” Lopez said. “I never caught him [cheating] but I just knew. He’d say he was going to a club for a couple of hours and then never come back that night.”

In 2015, Combs appeared on “The Breakfast Club” radio show and discussed the “deal” he made with his girlfriends in which he said that women could expect him to cheat.

“If I’m in a relationship with you, 25 percent of your time, you’re gonna just feel like, ‘Aw, man, I hate being here, this guy cheated on me, he lied on me,’” Combs said. “But then there’s 75 percent of ‘I’ma make you the happiest woman in the whole wide world. I’ma be there to support your dreams. I’ma be there to hold you, listen to you. I’ma be there to be your best friend. And I promise you’ll smile the most. You know who I am, this is what it is.’"

However, sources claimed to Rolling Stone that the Grammy winner didn’t fully disclose all of the so-called deal, and part of it was that the girlfriends weren’t allowed to walk away. Damien Vasquez, a former intern at Bad Boy Entertainment, claimed that was the reasoning behind Combs sending staffers to hold signs outside of the TRL studio.

A string of allegations against Combs have surfaced over the past six months, with several people filing lawsuits against the “Coming Home” artist, accusing him of sexual assault. Combs released a statement on December 6, 2023, denying all of the allegations.

“Enough is enough. For the last couple of weeks, I have sat silently and watched people try to assassinate my character, destroy my reputation and my legacy,” Combs stated. “Sickening allegations have been made against me by individuals looking for a quick payday. Let me be absolutely clear: I did not do any of the awful things being alleged. I will fight for my name, my family and for the truth.”

However, the allegations have led to a renewed interest in Lopez and Combs’ relationship, and a source exclusively revealed to In Touch that Lopez has no desire to revisit that time in her life.

“J. Lo is horrified by all of the accusations,” the insider said. “She and Diddy had talked about marriage at one point, but she left him for a reason. Now people want to know why and what she saw.”

The source continued, “There were many wild moments with Diddy, and it gives J. Lo the creeps to think that she was with him for so long,” shared the insider, noting that the superstar has previously spoken about him being unfaithful. “She wasn’t happy in the relationship.”