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Diddy’s Dating History: What to Know About the Rapper’s Relationships, from Jennifer Lopez to Cassie
Diddy has dated a number of famous women, including singer Cassie, who testified at his federal criminal trial in May 2025

Sean “Puff Daddy” Combs and Jennifer Lopez attend The 2000 MTV Video Music Awards ; Cassie Ventura and Sean Combs attend the “Can’t Stop, Won’t Stop: The Bad Boy Story” Premiere on April 27, 2017 in New York City.
Diddy and Jennifer Lopez in 2000; Cassie and Diddy in 2017.

Sean “Diddy” Combs’ dating history includes relationships with Jennifer Lopez, Cassie and Yung Miami
The rapper has welcomed seven children with four women
Cassie filed a lawsuit against Combs in 2023 and testified at his federal criminal trial in May 2025
The intimate details of Sean “Diddy” Combs’ personal life are being discussed at his ongoing federal criminal trial.

In September 2024, Combs was arrested and charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He pled not guilty and was denied bail multiple times ahead of his trial in New York City, which began on May 12.

The accusations against Combs first came to light when his ex-girlfriend Casandra “Cassie” Ventura filed a lawsuit against the rapper in November 2023, alleging that Combs raped and sexually trafficked her over the course of their decade-long relationship. The exes reached a settlement one day later.

In the following months, numerous other lawsuits were filed against Combs, accusing him of sexual assault, which he has denied. In March 2024, the rapper’s properties in Los Angeles, Miami and New York were raided amid allegations of sex trafficking.

Two months later, a video was released showing Combs allegedly abusing Cassie in a hotel in March 2016. Combs later confirmed it was him in the video and apologized for his actions.

Diddy’s Dating History: What to Know About the Rapper’s Relationships, from Jennifer Lopez to Cassie
Diddy has dated a number of famous women, including singer Cassie, who testified at his federal criminal trial in May 2025

By Rebecca Aizin and Samantha Stutsman Published on May 16, 2025 07:00AM EDT
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Sean “Puff Daddy” Combs and Jennifer Lopez attend The 2000 MTV Video Music Awards ; Cassie Ventura and Sean Combs attend the “Can’t Stop, Won’t Stop: The Bad Boy Story” Premiere on April 27, 2017 in New York City.

Sean “Diddy” Combs’ dating history includes relationships with Jennifer Lopez, Cassie and Yung Miami
The rapper has welcomed seven children with four women
Cassie filed a lawsuit against Combs in 2023 and testified at his federal criminal trial in May 2025
The intimate details of Sean “Diddy” Combs’ personal life are being discussed at his ongoing federal criminal trial.

In September 2024, Combs was arrested and charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He pled not guilty and was denied bail multiple times ahead of his trial in New York City, which began on May 12.

The accusations against Combs first came to light when his ex-girlfriend Casandra “Cassie” Ventura filed a lawsuit against the rapper in November 2023, alleging that Combs raped and sexually trafficked her over the course of their decade-long relationship. The exes reached a settlement one day later.

In the following months, numerous other lawsuits were filed against Combs, accusing him of sexual assault, which he has denied. In March 2024, the rapper’s properties in Los Angeles, Miami and New York were raided amid allegations of sex trafficking.

Two months later, a video was released showing Combs allegedly abusing Cassie in a hotel in March 2016. Combs later confirmed it was him in the video and apologized for his actions.

On May 13, Cassie was called to the witness stand at Combs’ trial. In her testimony, she claimed that the rap mogul “controlled” her life when they were together and forced her to participate in sexual encounters.

Prior to his relationship with the “Me & U” singer, Combs dated Jennifer Lopez from 1999 to 2001. He went on to welcome four children with the late Kim Porter, whom he started dating in the ’90s before their final split in 2007.

Combs also shares a son, Justin, with fashion designer Misa Hylton and a daughter, Chance, with his friend Sarah Chapman. In 2022, Combs announced the birth of his seventh child, Love, with Dana Tran.

From Jennifer Lopez to Cassie, here’s a complete look back at Sean “Diddy” Combs’ dating history.