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

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For almost three decades, Sean “Diddy” Combs held significant influence in the music industry, being one of the most sought-after figures in hip-hop. His label Bad Boy Records consistently set new records year after year. However, things took a drastic turn in 2023 when Cassie Ventura, his former girlfriend and R&B artist-model, filed a lawsuit against him. The accusations included rape, assault, and sexual trafficking during their relationship spanning over a decade.

Despite resolving the issue within a day, the news sparked a chain reaction, inspiring other victims to reveal their distressing experiences and accuse Diddy of heinous crimes. Now, he has been incarcerated for eight months and is standing trial on federal charges related to s*x trafficking, racketeering, and facilitating prostitution.

The incident in a hotel lobby that captured him brutally kicking, pulling, and hitting Ventura as she was attempting to exit the premises significantly tarnished his image. In his heyday, he was romantically linked to several prominent figures in the entertainment world, with Jennifer Lopez being one of them.

As a lifestyle connoisseur looking back, I’ve been blessed with the arrival of four beautiful children, shared with the late Kim Porter, who left us too soon. Additionally, I have a son named Justin, born from my collaboration with fashion designer Misa Hylton, and a daughter Chance, a precious gift from my dear friend Sarah Chapman. Fast forward to 2022, I’ve embraced the joy of fatherhood once more, welcoming Love into our family with Dana Tran by my side.

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

Misa Hylton

In the first half of the 1990s, Diddy was romantically involved with fashion designer Misa Hylton. Their single child, Justin, was born on December 30, 1993. Despite splitting up soon after their son’s birth, they have managed to maintain a strong friendship until the present day.

Kim Porter

In the 1990s, Porter and Diddy began dating. They had their first child together, Christian, on April 1, 1998. Their relationship was often up and down over the years. In 2006, when she was pregnant with his twins, D’Lila Star and Jessie James, Porter found out that he was expecting a child with his friend Sarah Chapman. Combs also adopted Porter’s first son from a past relationship, Quincy. They separated in 2007 but continued to keep in touch until her death in 2018 due to pneumonia.

Jennifer Lopez

In the late ’90s and early 2000s, I had the chance to date two powerhouses – JLo and Diddy. Our relationship lasted for almost two years, from 1999 to 2001. However, in a 2003 Vibe interview, the pop icon shared that infidelity was the cause of our separation. Remarkably, much like my past relationships, I managed to maintain a strong connection with JLo post-split.

Cassie Ventura

For approximately ten years, from around 2007 to 2018, Ventura was in a relationship with Diddy. During her testimony at the Manhattan court, she revealed extensive details about the abusive nature of their romance. However, they did not have any children together. Following their separation, Ventura married Alex Fine, a well-known fitness instructor and actor, in 2019. The couple currently has two daughters, with another son due between June and July of this year.

Yung Miami

Back in 2021, whispers began swirling around the music world about a potential connection between me and Diddy. However, it wasn’t until June of 2022 that we boldly stepped into the limelight and acknowledged our relationship to the world. But let me tell you, nothing beats the thrill of walking the red carpet at the Met Gala together in 2023 – a moment I will cherish forever!

Dana Tran

In October 2022, a cybersecurity expert, industrial consultant, and model named Tran gave birth to her child, Love, with the renowned artist Diddy. Although they didn’t publicly confirm their romantic involvement, they have been observed sharing parenting responsibilities and enjoying family trips together.

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2025-05-16 16:53