Diddy’s star-studded dating timeline revealed — inside the rapper’s most talked-about romances from Jennifer Lopez to Cassie Ventura

In September 2024, Sean John Combs known as Diddy was arrested and charged with sex trafficking, racketeering conspiracy, and transportation to engage in prostitution. He pleaded not guilty and was denied bail multiple times before trial started in New York City on May 12, 2025.

These charges reportedly first came to light after Cassie, his ex- girlfriend, filed a lawsuit in November 2023, saying Diddy raped her. They settled the lawsuit one day later, but more people filed lawsuits against him after that.

In March 2024, police raided his homes in Los Angeles, Miami, and New York for the sex trafficking case. In May 2024, a video leaked showing Diddy hitting Cassie in a hotel in 2016. He apologized and admitted it was him. On May 13, 2025, Cassie testified in court, saying Diddy controlled her life and forced her into sexual acts.

Diddy's Love Affairs and Kids

In the 1990s, Misa Hylton, a fashion designer whom Diddy helped in her career by hiring her to style Jodeci. They had a son, Justin, born Dec 30, 1993 and later broke up soon after but co-parented peacefully. In June 2023, Misa slammed Diddy on Instagram Stories after Justin got a DUI. She also took a dig at Diddy’s lawsuit with alcohol brand Diageo, saying he should sell something healthy. But later, they seemed okay, Diddy commented “I love you queen” on her post.

Diddy and Kim Porter, his ex, had a son in 1998, named Christain. Diddy and Porter were in an on again off again thing from the nineties to 2007. Diddy was also helping raise Quincy, Kim Porter’s son from another relationship. In 2006, while Kim was pregnant with their twin girls, she found out Diddy was having a baby with another woman, Sarah Chapman.

In an interview with Essence she said, she was hurt he didn’t tell her directly, according to reports. Their twins D’Lila Star and Jessie James were born in Dec 2006. Kim broke up with Diddy for the last time in July 2007, saying she needed to move on. Didi was friends with Kim till she breathed her last, in 2018. Diddy still posts tributes to her.

Later in 1999 he started dating Jennifer Lopez. They dated for 2 years, went to the 2000 Grammys together. In a 2003 Vibe interview, J.Lo said they broke up because Diddy cheated. In 2017, Diddy told Entertainment Tonight that J.Lo was “one of my greatest loves”, according to the reports.

In 2006, Diddy and Sarah Chapman had a daughter, while they were reportedly just friends and he was still with Kim Porter at the time. Diddy and Sarah were co-parenting. Diddy gave Cassie an insta shoutout on her birthday in September 2023, thanking her for being in his life, before she took him to court in November of the same year.

Cassie accused him of 'bad' treatment like drugs, abuse, and other serious allegations. She also said he once broke into her place.

Diddy denied everything, and his lawyer said it was blackmail. The case was wrapped up in a day, after a settlement, and no more details were shared. Her case later led to a federal investigation and Diddy’s 2024 arrest. Cassie testified again in 2025, according to the reports. Cassie later got hitched to trainer Alex Fine, and has two kids with him, with a third reportedly on the way.

In 2019, Diddy was in the middle of another swing of dating rumours with Lori Harvey, after he was seen with her in New York. Both were also seen on a holiday together, with their respective families, in Italy. In October that year, Lori mysteriously unfollowed him, allegedly after Diddy was seen hobnobbing with another woman. Later in 2023, Lori quashed rumours of her dating either Diddy or his son Justin, calling the rumour mongering "absolutely not true".

Diddy was then linked with Yung Miami in 2021. Miami confirmed in June 2022 that they were dating but she also said they were still single. In an interview with XXL Mag she said that people didn’t understand what "dating" meant to them, according to the reports. Both of them did not officially make any announcement of breaking off.

Diddy has seven kids. His first son, Justin, was born in 1993 with Misa Hylton. He had Christian in 1998 and twin girls, D’Lila Star and Jessie James, in 2006 with Kim Porter. He also raised Kim’s son Quincy like his own. Diddy has a daughter with Sarah Chapman; and his youngest daughter, Love, born in 2022 with Dana Tran.

FAQs

Q1. Why is Diddy arrested?
He is charged with sex trafficking, abuse, and other crimes.

Q2. Who is Diddy's ex Cassie and what's her opinion about Diddy?
Cassie is Diddy’s ex girlfriend who said he abused and controlled her.