Were Diddy and Jennifer Lopez dating? A look at their relationship history

Jennifer Lopez and Sean Diddy Combs were two titans of the entertainment industry who ignited a whirlwind romance, capturing the attention of fans and media alike. Their relationship came into the public eye in September 1999, when they appeared together at the MTV Video Music Awards, marking their first official public outing as a couple.

Known for their high-profile status, the duo frequently made headlines as they were spotted at glamorous events, like the 42nd Annual Grammy Awards in February 2000. At the event, Lopez wore a plunging green Versace dress, which caught the eye of the media and stole the show, symbolizing their status as a power couple.

Throughout their relationship, both stars openly expressed their admiration for each other. In interviews, Lopez often described Combs as charismatic and influential in the music industry, while Combs praised Lopez for her unparalleled talent and style.

But their relationship faced challenges that were marked by legal troubles in December 1999, when they were both arrested in connection with a nightclub shooting in New York City. Although charges against Lopez were dropped, the incident added strain to their relationship.

Their romance ultimately concluded in February 2001. The news of their breakup was confirmed through a press release, distributed to multiple media outlets rather than on social media or through a direct interview.

Jennifer Lopez and Diddy's relationship timeline, explored

1999 MTV Video Music Awards (Image via Getty)

September 1999: Diddy and Jlo's first public couple appearance

In the late 1990s, Jennifer Lopez and Sean Diddy Combs became one of the most glamorous and talked-about couples in the entertainment industry.

Their story began in 1999 when Lopez was filming the music video for her hit single If You Had My Love, a project that introduced her to Combs. The connection was instant, and by September 1999, they made their first public appearance as a couple at the MTV Video Music Awards, setting off a flurry of media attention.

February 2000: The couple's Grammy Awards appearance

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Their relationship continued to draw the spotlight at the 42nd Annual Grammy Awards in February 2000, where Lopez wore the now-iconic green Versace dress. Reflecting on that night, Diddy told Entertainment Tonight in a 2017 interview,

“She deserved it. She is one of the fliest out there.”

February 2001: Diddy and Jlo break up

By February 2001, the couple decided to go their separate ways. The breakup was confirmed through a press release distributed to multiple media outlets - a common practice for high-profile separations at the time. Lopez later opened up about the reason for their split to Vibe, primarily attributing it to Diddy's infidelity.

"It was the first time I was with someone who wasn't faithful. I never caught him, 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," she stated.

July 2003: Lopez opened up about their controversial relationship

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The duo's relationship was not without its challenges. In December 1999, both were embroiled in a serious legal matter after a shooting incident at a New York City nightclub. The couple fled the scene, and Diddy was later charged with weapons and bribery offenses, though he was acquitted in March 2001. Lopez was detained but not charged.

Recalling the ordeal, Lopez discussed the emotional strain it placed on her, telling Vibe in a 2003 interview,

"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."

September 2018: The former couple share a friendly hug at a party

Despite the end of their romance, both Lopez and Diddy have periodically revisited their past in public discussions. In various interviews, Lopez has spoken about the lessons learned from their time together, and the importance of self-worth and trust in a relationship.

Meanwhile, Diddy has consistently expressed admiration for Lopez's talent and personality. At her All I Have Las Vegas residency party in 2018, captured by TMZ, the former couple shared a friendly hug, displaying the cordial nature of their relationship.

April 2020: Jennifer Lopez and Diddy's Instagram live reunion

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Jennifer Lopez and Sean Combs teamed up for a charitable dance-a-thon on Instagram Live to support Direct Relief's COVID-19 efforts, as reported by Billboard on Saturday, April 11, 2020, before the event. The virtual event took place on Sunday, and saw the participation of Lopez and her fiancé Alex Rodriguez, along with Combs and his sons.

During the live session, Combs expressed his affection for the new couple, saying,

“Hey, I love you guys, I can’t wait until we can see each other again. May God bless y’all, and I just love you guys!”

To this, Jennifer responded,

“We love what you’re doing, we love everybody out there. We want to send you all the love in the world, from our family to yours.”

May 2021: Diddy posts a throwback photo with Lopez

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In May 2021, amidst news of Lopez rekindling her romance with Ben Affleck, Diddy posted a throwback photo of himself with Lopez, stirring speculation. However, the post was later removed.

He clarified his intentions in an interview with Vanity Fair in August 2021, stating,