Celebrity
Sean ‘Diddy’ Combs dated Jennifer Lopez for about two years between 1999 and 2001. The couple’s breakup was hard on them, and both have previously spoken out about the relationship.
Hip-hop mogul Sean ‘Diddy’ Combs was once the guy everyone wanted to be friends with. He was known for wild parties (that cost upward of $500,000 each), and in the early 2000s, he dated plenty of high-profile people. But one of his most well-known relationships was with singer and actor Jennifer Lopez, whom Diddy dated for about two years between 1999 and 2001.
Diddy eventually opened up about his relationship, saying that therapy helped him get over the breakup.
Sean ‘Diddy’ Combs relationship with Jennifer Lopez had a strong impact on him
When Diddy and JLo started dating in the late 1990s, they were both just starting what would eventually be decades of fame. They were essentially equals when it came to how known they were, and at that time, it only made sense that they dated. However, the romance didn’t last. Diddy and JLo were often caught up in controversy, including a situation at a night club that involved someone getting shot.
JLo eventually opened up about the relationship from her perspective. “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,” JLo told Vibe magazine a couple years after the split. “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.”
And Diddy said that he had a hard time moving on from JLo, too. “Well, you know, I wish her the best in her life. I always have,” Combs told The New Yorker in 2002, according to OK! Magazine. “But … Look, if she is happy, then I am happy for her.”
Diddy also said in an interview with Playboy that therapy was helpful. “I’ve gone to therapy for relationships I’ve been in, for tragedies I’ve been through. I think therapy is good,” he said. “I’ve had therapy about my relationship with Kim [Porter], about my relationship with Jennifer. Therapy helped me through a lot of those situations.”
Sean ‘Diddy’ Combs is currently awaiting trial on numerous charges
Diddy has had nothing short of a fall from grace over the last year. Back in 2023, his ex, Cassie Ventura, sued him for abuse, and eventually footage was released of Diddy abusing Cassie in a hotel hallway. Then, after a lengthy investigation, Diddy was arrested in 2024 on allegations including sex trafficking and racketeering.
Celebrities have mostly abandoned Diddy, with only his family seemingly staying at his side through the legal battles. Most people don’t want to be associated with him, and more women have come forward detailing their experiences with the mogul. Diddy’s trial is scheduled to begin in May 2025.
