Sean “Diddy” Combs has been in the news as of late due to some serious allegations, including a lawsuit filed by his ex-girlfriend Cassie, which has accused him of rape, sexual trafficking, and more.
The controversy has brought to light Diddy’s extensive history of high-profile relationships since his rise to fame in the 1990s. The rapper has been romantically linked to several celebrities, including Jennifer Lopez, Cassie Ventura, and his longest relationship Kim Porter, whom he dated in the ’90s before their final split in 2007.
Diddy and Porter, who passed away in 2018, shared four children together: Quincy, Christian, Jessie, and D’Lia. In addition, the R&B artist has a son, Justin, from his relationship with fashion designer Misa Hylton, and a daughter, Chance, with a friend named Sarah Chapman. In 2022, he surprised many when he announced he welcomed a seventh child, Love, with a cybersecurity specialist and model Dana Tran.
Following Cassie’s lawsuit, multiple other allegations of sexual assault surfaced against Diddy, which he has vehemently denied. In March 2024, his properties were raided amid claims of sex trafficking, and a disturbing video from 2016, allegedly showing him abusing Cassie, emerged. Diddy was arrested in September 2024, facing charges including sex trafficking and more, but he pleaded not guilty and was denied bail.
From Jennifer Lopez to Cassie, here’s a complete look back at Diddy’s dating history throughout the years.
Misa Hylton
One of Diddy’s first notable relationships was in the 1990s with Hylton. Their relationship led to the birth of his first son in 1993. Hylton played a significant role in his early career, helping him with style choices for artists at Uptown Records. “He had a new position at Uptown Records and he was in charge of putting together the album musically but also for their look,” she recalled to BET in March 2023. Despite their breakup, they have maintained a close co-parenting relationship through the years.
Kim Porter
One of Diddy’s most notable relationships was with Porter, whom he began dating in the ’90s after his split from Hylton. Together, they had three biological children, a son named Christian, and twin daughters D’Lila Star and Jessie James. Diddy also had another child named Quincy from a previous unnamed relationship that the couple parented.
Their relationship had its ups and downs, especially when Porter discovered the producer was expecting a child with another woman, Sarah Chapman, while she was pregnant with their twins. Despite this betrayal, they managed to stay connected and co-parent their children. After their final breakup in 2007, Porter said, “In ending this relationship, I made a decision that was in the best interest of myself, Sean, and our family.” Following her tragic death in 2018, Diddy frequently honored her memory on social media posts that have since been removed.
Sarah Chapman
While still involved with Porter, Diddy welcomed a daughter, Chance, with Chapman. Their relationship has been primarily platonic, centered around co-parenting their child. Diddy expressed gratitude for the business woman’s role, saying, “Thank God for you every day! We are so grateful to have you in our lives!” in a post on Instagram that has now been removed.
Jennifer Lopez
Diddy’s high-profile romance with Lopez began in 1999 and lasted until 2001. Their relationship quickly became the talk of the town, especially after their appearance at the 2000 Grammy Awards.
The “I’ll Be Missing You” artist later described her as “without a doubt, one of my greatest loves,” in a 2017 interview with Entertainment Tonight. Though they parted ways due to infidelity, he has spoken fondly of their time together, saying to the outlet that he, “Didn’t know how big it was gonna be, but it was a great moment for her.”
Cassie Ventura
Following his final breakup with Porter in 2007, Diddy began a long and tumultuous relationship with singer Cassie later that same year. After their breakup in 2018, Cassie made serious allegations against Diddy, filing a lawsuit in November 2023 that accused him of rape, sexual trafficking, among other things throughout their relationship.
The complaint detailed a pattern of control and abuse, claiming that Diddy exerted “complete control” over her life, often resorting to violence. One of the most shocking pieces of evidence was a video released in May 2024, showing Diddy allegedly assaulting Cassie in a hotel in March 2016.
Lori Harvey
In 2019, Diddy sparked dating rumors with Lori Harvey, the daughter of comedian Steve Harvey. Their relationship was brief, as Harvey unfollowed Diddy on social media shortly after they were seen walking together in New York City’s Soho neighborhood. However, Harvey has denied the relationship rumors.
Yung Miami
Diddy was first linked to rapper Yung Miami in 2021 but waited until 2022 to talk about their relationship via her podcast Caresha Please. When asked what their relationship status was by Young Miami, Diddy responded, “We date. We’re dating. We go have dates. We’re friends. We go to exotic locations. We have great times.” She later clarified their situation to XXL Magazine, saying, “We are dating. We’re single, but we’re dating,” emphasizing their casual approach.
Dana Tran
The music mogul welcomed a child named Love with Tran in October 2022, though he has never confirmed their relationship. “I’m so blessed to welcome my baby girl Love Sean Combs to the world,” he wrote on X (formerly known as Twitter).
If you or someone you know has been the victim of sexual assault, please call the RAINN national helpline for support: 800.656.HOPE (4673).
