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Jennifer Lopez and Sean “Diddy” Combs began dating in 1999, not long after her divorce from her first husband. The pair were together, on and off, for two years before calling it quits for good in 2001. Lopez said that her two years with Diddy were tumultuous. She strongly suspected him of cheating on her, and he frequently told her he wanted their relationship to end. Even though they weren’t married, he told her he wanted a divorce.

Sean ‘Diddy’ Combs and Jennifer Lopez had a tumultuous relationship

When Lopez was still with Diddy, she hinted at problems in their relationship. Their careers made it difficult for them to see each other and he frequently told her that he wanted to break up as a result. 

“It’s a lot. He’s said to me many times, ‘I want a divorce,’” Lopez told Rolling Stone in 2001. “I’ll be away so much, or he’ll be … he can’t get away, whatever, but he’ll say, ‘So, where do I send the papers?’”

Sean 'Diddy' Combs wears a suit and sits with his arm around Jennifer Lopez's shoulder. She wears a shiny halter dress.
Sean “Diddy” Combs and Jennifer Lopez | Kevin Winter/ImageDirect

She said that even when they were together, they struggled to get on the same page.

“Puff loves to go out,” she said. “He’s been a going-out-to-clubs person all his life, doing his thing. I’ve always been a homebody. So we switch off what we do when we’re together. I don’t really like to talk about us, because I don’t feel like it’s anybody’s business. It’s a separate thing. He’s an artist, I’m an artist, we have two separate careers.”

Jennifer Lopez said Sean ‘Diddy’ Combs exhausted her

After their breakup, Lopez admitted that her dynamic with Diddy had been a challenge. For her, it came as a relief when things ended.

“It wasn’t a great time in my life,” she told Vanity Fair, referencing the 1999 club shooting. “It was scary. And we broke up many times before that, and got back together and broke up again, and nobody knew about it. It was very tempestuous. Towards the end it was emotionally exhausting. It was good that I was young.”

She said that all through their relationship, she had a nagging feeling he was cheating on her. While she never caught him in the act, she’s confident her gut feeling was right.

She said she was not comfortable with his behavior when they first met

Lopez and Diddy met on the set of the “If You Had My Love” music video. He told her he loved her shortly after meeting, before they were involved.

“I was like, This guy is crazy,” she said. “I said, ‘You don’t even know me.’”

Sean "Diddy" Combs wears a suit and sits with his arm around Jennifer Lopez, who wears a magenta dress.
Sean ‘Diddy’ Combs and Jennifer Lopez | KMazur/WireImage
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She tried to put distance between them, but he continued to pursue her.

“I kept him at a distance, but then he kept calling me and I guess it was exciting at the beginning,” she said. “He was from New York, I was from New York, we just kind of spoke the same language, and we both had a love of music. He sort of mentored me and was very sweet in the beginning.”