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Sean “Diddy” Combs, once a dominant force in hip-hop and founder of the legendary Bad Boy Records, has faced a dramatic and troubling fall from grace since 2023. That year, his former girlfriend, R&B singer and model Cassie Ventura, filed a highly publicized lawsuit accusing him of rape, assault, and sex trafficking during their nearly decade-long relationship. Although the two quickly settled the lawsuit, the allegations sparked other accusers to come forward, leading to Diddy’s ongoing federal trial on charges including sex trafficking, racketeering, and transportation for prostitution. He has already spent eight months in prison amid the case.
What intensified the damage to his reputation was a widely circulated hotel lobby video showing Diddy violently kicking, dragging, and punching Ventura as she tried to leave the premises—an image that shocked many given his former status as a music mogul.
Here’s a list of Diddy’s notable relationships over the years:
- Misa Hylton: The fashion designer and stylist dated Diddy in the early 1990s. They have one son together, Justin, born in 1993. Though they separated soon after, they reportedly remain on friendly terms.
- Kim Porter: Diddy’s longtime partner throughout the 1990s and early 2000s. Together, they had three children: Christian (born 1998), and twins D’Lila Star and Jessie James (born 2006). Diddy also adopted Kim’s son Quincy from a previous relationship. Their relationship was famously tumultuous, including a difficult period when Porter was pregnant with twins and discovered Diddy was expecting a child with another woman. The couple separated in 2007 but stayed close until Porter’s untimely death from pneumonia in 2018.
- Jennifer Lopez: Diddy and JLo dated from roughly 1999 to 2001. Their breakup was reportedly due to his infidelity, but the two maintained a friendly relationship afterward.
- Cassie Ventura: They were together for nearly ten years (2007–2018). Their relationship ended amid serious allegations and the ongoing legal battles. Cassie later married celebrity trainer and actor Alex Fine in 2019, with whom she has two daughters and is expecting a son.
- Yung Miami: The rapper and Diddy were linked starting in 2021 and confirmed their relationship publicly in 2022. They made a high-profile appearance together at the 2023 Met Gala.
- Dana Tran: A cybersecurity professional, model, and industrial specialist, Dana gave birth to Diddy’s seventh child, a daughter named Love, in October 2022. Though the couple never confirmed their romantic relationship, they have been seen co-parenting and vacationing together.
This turbulent personal history, marked by both high-profile relationships and serious allegations, stands in stark contrast to Diddy’s legendary career in music and business. The ongoing trial and public scrutiny will likely define this new, difficult chapter in his life.