Sean ‘Diddy’ Combs had a high-profile relationship with Jennifer Lopez and in a resurfaced interview, he admitted he was hoping ex Kim Porter would take him back.

Sean ‘Diddy’ Combs once confessed that he dated Jennifer Lopez with the ulterior motive of making his ex-girlfriend Kim Porter jealous, hoping she would “come running after me.”

The founder of Bad Boy Records, now 55, had a tumultuous relationship with J. Lo from 1999 to early 2001, all while harboring lingering feelings for Kim.

In a throwback interview with Essence magazine in 2007, Diddy candidly discussed the strategy behind his high-profile romance, admitting: “I thought, ‘I’ll test the waters and hopefully Kim will see I’m serious and come running after me’.”

Despite describing Jennifer as his “perfect match,” it appears that wasn’t sufficient to sustain their relationship.

Kim, on her part, was not fooled by Diddy’s actions. In the same Essence interview, she revealed her insight into his true feelings, stating: “I knew what was really going on. He was still in love with me.”

Kim Portner got back together in 2003 (Image: Getty Images)

In that revealing conversation with Essence, Diddy also delved into the reasons he was drawn to Kim initially, which ironically were the same reasons that eventually drove them apart.

He reflected on his need for attention and admiration, saying: “I’m used to applause when I walk in the room. And [Kim] was just too cool,” indicating that her composure and lack of awe towards him were both attractive and challenging.”

Combs remarked: “I would tell her, ‘I guess I’ll go be with someone else who’ll take care of me the way I want to be taken care of, who’ll be a little more aggressive.'”

Diddy and Jennifer Lopez did not work out (Image: Getty Images)

Kim and Diddy patched things up in 2003, only to part ways permanently in 2007.

The interview has come back into the spotlight as the “Last Night” rapper is currently detained at Brooklyn’s Metropolitan Detention Center.

Arrested in September on accusations of sex trafficking, racketeering conspiracy, and transportation for prostitution, Combs has fiercely rejected all charges and entered a not guilty plea in court.

Awaiting his federal trial set for May 2025, Diddy faces multiple lawsuits from Texas attorney Tony Buzbee, including claims of rape, sexual abuse, and assault—all vehemently denied by Diddy.

Combs’ lawyer Erica Wolff addressed the lawsuit announcements, stating: “We cannot address every meritless allegation in what has become a reckless media circus.

“That said, Mr. Combs emphatically and categorically denies as false and defamatory any claim that he sexually abused anyone, including minors.

“He looks forward to proving his innocence and vindicating himself in court if and when claims are filed and served, where the truth will be established based on evidence, not speculation.”