Did You Know Diddy Once Dated Jennifer Lopez? Revisiting His Dating History and Past Girlfriends

Trigger Warning: This article contains mentions of s*xual abuse. 

Sean "Diddy" Combs ruled the music industry for nearly three decades. He was among the most sought-after names in the hip-hop music scene, with his label Bad Boy Records crossing new milestones every year. But things changed in 2023 when his ex-girlfriend and R&B singer-model Cassie Ventura filed a lawsuit against him, alleging that the music mogul r*aped her, assaulted her, and even s*xually trafficked her over the course of their decade-long relationship.

Even though the two reached a settlement in less than 24 hours, the news caused a ripple effect, and several other victims came forward to share their horrific stories and accused Diddy of some horrendous crimes. Now, he has been in prison for eight months and is currently on federal trial on charges of s*x trafficking, racketeering, and transportation for pr*stitution.

What deeply damaged his reputation was a viral video from a hotel lobby that showed him kicking, dragging, and punching Ventura while she was trying to leave the property. During his prime days, he dated some really famous women in the industry, with Jennifer Lopez being one of them. 

He later went on to welcome four children with late Kim Porter. He also shared a son named Justin with fashion designer Misa Hylton and a daughter named Chance with his friend Sarah Chapman. In 2022, he welcomed his seventh child, Love, with Dana Tran.

Here's a look at his dating history and past girlfriends!

Misa Hylton

Diddy dated fashion designer Misa Hylton in the early 1990s. They welcomed their only child, Justin, on December 30, 1993. The pair broke up shortly after their son's birth but remain close friends even today.

Kim Porter

Porter and Diddy also started dating in the 1990s. They welcomed their first child together, Christian, on April 1, 1998. They went on to have an on-again, off-again relationship for years. In 2006, when she was pregnant with Diddy's twins, D'Lila Star and Jessie James, she discovered he was expecting a child with his friend Sarah Chapman. Combs also adopted Porter's first son from a previous partner, Quincy. The two parted ways in 2007; however, they remained in touch until she died in 2018 from pneumonia.

Jennifer Lopez

JLo and Diddy dated for nearly two years between 1999 and 2001. The pop icon cited infidelity as the reason for their split in a 2003 Vibe interview. Just like his previous relationships, he maintained a close bond with JLo even after their split.

Cassie Ventura

Ventura and Diddy dated for nearly a decade between 2007 and 2018. She has shared details of her abusive relationship in depth on the stand of the Manhattan court. The two didn't have any children. After their split, Ventura went on to marry celebrity personal trainer and actor Alex Fine in 2019. The two already have two daughters and are expecting a third child, a son, anytime in June or July.

Yung Miami

Miami and Diddy were first linked in 2021, and they first confirmed their relationship in June 2022. The two even attended the Met Gala together in 2023.

Dana Tran

Tran, who is a cybersecurity professional, industrial specialist, and model, welcomed her daughter Love with Diddy in October 2022. The two never confirmed their relationship but have been seen coparenting and going on family vacations.

Disclaimer: If you need support or know someone who is struggling with domestic violence or assault, or abuse, please reach out to your nearest mental health specialist or NGO or speak to someone about it. There are several helplines available for the same.

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