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Sean “Diddy” Combs and Jennifer Lopez were together on and off for two years. During their relationship, Lopez began to suspect that he was not faithful to her. She described their final days together as being incredibly hard on her. Diddy’s friend, however, thought Diddy was the wronged party. He believed that Lopez proved herself to be disloyal during the breakup. 

Sean ‘Diddy’ Combs’ friend did not think highly of Jennifer Lopez 

On Dec. 27, 1999, Lopez, Diddy, and friends were at a club in New York. At some point in the night, gunfire erupted, injuring three people. Diddy and Lopez fled the scene, but they were later arrested with Bad Boy artist Moses “Shyne” Barrow. Lopez escaped without charges, but Diddy and Barrow did not. A jury acquitted Diddy in the 2001 trial, but Barrow received a prison sentence

While Diddy escaped prison time, Lopez broke up with him during the trial. When asked how he felt about her leaving him at this time in his life, Diddy answered carefully.

Sean 'Diddy' Combs walking in front of Jennifer Lopez. Lopez is smiling and looking over her shoulder.
Sean ‘Diddy’ Combs and Jennifer Lopez | Steve Granitz Archive 1/WireImage

“Well, you know, I wish her the best in her life. I always have,’’ he told The New Yorker in 2002. “But … Look, if she is happy, then I am happy for her.’’

His friend, who was present for the interview, was not as diplomatic. They disliked the fact that Lopez left Diddy during that challenging period in his life.

“Disloyal b****,’’ the friend said disdainfully. “She’s nothing but a disloyal b****.”

Jennifer Lopez did not believe Sean ‘Diddy’ Combs was loyal to her

Lopez did not view herself as disloyal. She believed that Diddy was the disloyal one in that relationship. 

“It was the first time I was with someone who wasn’t faithful,” she told Vibe Magazine (per Entertainment Weekly). ”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.”

While she never got definitive proof that he was cheating, she knew in her gut that it was true.

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

He reportedly had a hard time letting her go

While Diddy claimed that he just wanted to see Lopez happy, he reportedly had a hard time moving on from the relationship. Former Bad Boy intern Damien Vasquez alleged to Rolling Stone that Diddy sent people to “camp outside MTV’s TRL studios with signs to win her back.” He also began therapy to help him move past the relationship.

Sean Diddy Combs sitting next to Jennifer Lopez at a fashion show.
Jennifer Lopez and Sean Diddy Combs | Stephane Cardinale/Getty Images
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“I’ve gone to therapy for relationships I’ve been in, for tragedies I’ve been through. I think therapy is good,” Diddy once told Playboy (via Contact Music). “I’ve been called bipolar – I’m not; I just have very drastic mood swings. I went to therapy when Big died, but a lot of my therapy has been with love and relationships. I’ve had therapy about my relationship with Kim [Porter], about my relationship with Jennifer. Therapy helped me through a lot of those situations.”