As the trial of Sean 'Diddy' Combs continues in New York, all eyes are on the music mogul and his past relationships. He faces charges of sex trafficking, racketeering and transportation to engage in prostitution as well as a slew of other civil charges alleging sexual assault and abuse. Diddy denies all allegations and has pleaded not guilty in court.
As some of the more sordid details from his past have been dredged up in court, many people want to know more about his romantic history, including who he has publicly dated and who he shares his seven children with.
Sean 'Diddy' Combs' past girlfriends
Misa Hylton
When Diddy was just starting out in the music industry in the early '90s, before he started his own label in 1993, he dated fashion designer Misa Hylton. Diddy and Misa welcomed a child together called Justin in 1993. Their relationship ended shortly after but they reportedly remained close, with Misa attending Diddy's 50th birthday party in 2019.
However, in 2023, when their son was arrested and charged for a DUI, Misa called out her ex for his alcohol business ventures on social media. 'How [do] you go from one of the greatest to ever do it to making all your money off alcohol and suing the damn alcohol company,' she wrote. 'Sell something healthy that builds people up. I’m sick of it!!!!! NOT MINES.'
Kim Porter
After Misa, Diddy started dating Kim Porter. In 1998, their son Christian was born, and Diddy also considers Kim's first son Quincy as his own. Despite breaking up a year later and entering a custody battle, the exes remained close and were in an on-off relationship for years.
Kim later had twins with Diddy, D'Lila Star and Jessie, who have appeared in court during their father's trial, in 2006. Diddy was also expecting a child Sarah Chapman at the time, which she found out about through a friend, and Kim admitted this made her feel betrayed. 'I would have preferred to find out from him because that's a man,' she said. Diddy told her once his child with Sarah was born. 'For me, once the respect is gone, I'm not even listening to you,' she said.
In 2007, the couple split up for the final time. The pair remained close friends until Kim died from pneumonia in 2018.
Jennifer Lopez
In 1999, Combs started dating Jennifer Lopez and they were together for two years before breaking up in 2001. In 1999, JLo and Diddy were arrested after a night out in New York turned violent and they were pulled over by the police after a gunfire incident where three people were injured. J Lo was released without charges after 14 hours in custody, but Diddy faced weapons and bribery charges. He was later acquitted.
In a 2003 interview with Vibe, J Lo admitted that Diddy's alleged infidelity and partying is what led to their split. 'It was the first time I was with someone who wasn't faithful,' she said. 'I was in this relationship with Puff where I was totally crazy and going nuts, it really took my whole life in a tailspin.'
In an interview in 2017, Diddy said J Lo was 'without a doubt' one of the loves of his life and they have remained friendly over the years.
Sarah Chapman
Diddy and his friend the businesswoman Sarah Chapman never formally dated, but they welcomed a daughter called Chance together in 2006. For Chance's birthday in September 2023, Diddy posted on Instagram to say, 'Thank God for you everyday! We are so grateful to have you in our lives! Love you.'
Cassie
Diddy's most prominent relationship, at least in recent years, was with the singer Casandra 'Cassie' Ventura. The pair dated on and off for ten years after meeting in 2007 when Cassie was 19 and Diddy was 37 and he signed her to his label, Bad Boy Records. They broke up for good in 2018.
In 2023, she filed a lawsuit against him alleging that the rapper subjected her to a pattern of control and abuse for a decade. The case was settled out of court for $20 million (£14.7m).
However, in May the following year, CCTV footage was leaked online that showed Diddy violently beating and kicking Cassie outside their hotel room. It came at the same time as Diddy was under federal investigation. He was arrested in September and the video was played in court during his trial in May.
Cassie, who was eight months pregnant with her and her husband Alex Fine's baby at the time, told the court of the alleged abusive nature of her relationship with Diddy. 'I can't carry this anymore,' she said. 'I can't carry the shame, the guilt, the way he treated people like they were disposable. What's right is right, what's wrong is wrong. I came here to do the right thing.'
Lori Harvey
Diddy was rumoured to be dating Lori Harvey in 2019 after they were seen walking around New York's SoHo area. The following month they were spotted on holiday in Italy with Lori's parents. A few months later, though, Lori unfollowed Diddy on social media and their romance seemingly ended.
Yung Miami
In 2021, Diddy was linked to City Girls rapper Yung Miami. He confirmed the relationship on her podcast a year later when she asked 'what we is?' and Diddy replied, 'We're dating. We go have dates. We're friends. We go to exotic locations. We have great times.'
In September 2022, Yung Miami explained that she is still 'single' even though they are dating. 'He's single, I'm single, but we're dating,' she added. However, in May 2023, they attended the Met Gala together.
Dana Tran
Diddy's most recent relationship, then, was with Dana Tran. Despite never being publicly confirmed, the rapper welcomed a baby called Love in October 2022. Sharing the news on X he wrote, 'I'm so blessed to welcome my baby girl Love Sean Combs to the world. Mama Combs, Quincy, Justin, Christian, Chance, D'Lila, Jessie and myself all love you so much!'
Of course, various other individuals have testified about their experiences with Diddy over the years. He currently faces potentially more than 100 accusations of sexual assault over a 20 year period. One of his recent former partners has also testified during his sex trafficking trial under 'Jane' to remain anonymous. She said, 'I resent him for leading me into the lifestyle he led me to. I resented the way he went about introducing me to this lifestyle.'
The trial of Sean 'Diddy' Combs continues and is expected to last eight weeks.