Jennifer Lopez and Diddy's Relationship Timeline, Explained

The pair dated for two years.

By Brenda Alexander

Jennifer Lopez has been with some of Hollywood's most sought-after bachelors. While she's now proudly Mrs. Ben Affleck, getting to the altar with the actor took her kissing many frogs and several heartaches and marriages to get it right. She's always professed that Affleck was her greatest love, but one of her most famous with Sean "Diddy" Combs. 

Though Diddy was in a relationship at the time he met Lopez, he told E! News that the Selena star was the first woman he'd ever fallen madly in love with. Their relationship was public and had many highs and lows. Ultimately, they didn't last but made a lasting impression in popular culture. 

How they met

The two met when Diddy was an already established force in the music industry. They met on the set of a music video in 1999 when Lopez's singing career was just getting started.

Merging cultures

During their time together, Lopez benefited greatly from Diddy's hip-hop influence. She began collaborating with rappers during this time and released a string of hits. They were also considered to be one of the best-dressed couples in Hollywood. Diddy had already been a big player in the fashion industry and started his clothing line, Sean John. Lopez was his date at the 2001 Grammy Awards where she donned the infamous Versace dress. "He gave me so many cues and taught me so many things," she told Access Hollywood in 2014. "I'll always be grateful to him for that.

A love triangle?

According to Diddy's longtime on-again-off-again love and the mother of three of his children, Kim Porter, Diddy began a relationship with Lopez while they were together and she broke things off. But she claimed he never stopped trying to woo her back, even while with Lopez. There was even a nasty child support case between Diddy and Porter. After he and Lopez split in 2001, he and Porter reconciled.

The arrest

Lopez spent an evening in New York City partying to ring in 2000 on New Year's Eve. At some point in the evening while out at a nightclub, Diddy got into a verbal spat with someone. Shots rang out, and people were injured.

They reportedly fled the scene but were stopped by police. A 9-mm. handgun was found in the car hidden under one of the seats near Lopez's feet. They were both arrested and booked, and Lopez reportedly spent the evening fearful and in tears. She was not charged with a crime but Diddy stood trial and was found not guilty.

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A split

While they survived the arrest, sources claimed their relationship was downhill from there. By 2001, they split. Many believe Lopez felt Diddy's bad-boy ways were not good for her career and image.

Was there cheating?

Lopez initially told Oprah Winfrey that she never caught Diddy doing anything while they were together but she's since confirmed he cheated. "It was the first time I was with someone who wasn't faithful," Lopez told VIBE in 2003. "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."

In addition to the cheating, there were major lifestyle differences. She referred to herself as "a homebody" during a 2001 interview with Rolling Stone. The mogul was not. "Puff loves to go out," she said at the time. "He's been a going-out-to-clubs person all his life, doing his thing."

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