A look at Sean Diddy Combs' dating history: All on music mogul's ex-girlfriends

Diddy has been linked to several prominent women, including Kim Porter, Cassie Ventura, Jennifer Lopez, and Lori Harvey

Sean “Diddy” Combs is currently facing a storm of legal troubles, including federal charges related to sex trafficking, racketeering, and sexual assault. As investigations unfold and multiple accusers come forward, public interest in the rapper’s personal life — particularly his past relationships — has intensified, as reported by People.

Diddy has been connected to a number of well-known women in the fashion and entertainment sectors (AFP)

Over the decades, Diddy has been linked to several high-profile women across the entertainment and fashion industries. While some of these relationships were romanticised in the public eye, others have recently resurfaced under a darker lens as reported by Page Six.

Here’s a look at the most prominent women Diddy has dated:

1. Kim Porter

The late Kim Porter, a model and actress, was Diddy’s long-term partner and the mother of three of his children. Their on-and-off relationship spanned over a decade, and she remained a central figure in his life until her untimely death in 2018. Diddy has often spoken of Porter as his soulmate and credited her with helping shape his family life, as reported by Newsweek.

2. Cassie Ventura

Singer and model Cassie Ventura had a nearly decade-long relationship with Diddy. While their partnership often appeared glamorous in public, it later became the focus of legal attention when Cassie accused Diddy of years of abuse, coercion, and control. Their lawsuit was settled privately, but it helped spark further scrutiny into Diddy’s past, as reported by Legit.

3. Jennifer Lopez

In the late 1990s and early 2000s, Diddy was romantically involved with pop star and actress Jennifer Lopez. The relationship was widely publicised and included a controversial nightclub incident involving gunfire. Though they eventually parted ways, their time together remains one of the most talked-about celebrity romances of the era.

4. Lori Harvey

In 2019, Diddy was linked to Lori Harvey, the stepdaughter of TV host Steve Harvey. The relationship sparked widespread discussion, not only due to the significant age difference but also rumors that Diddy had previously dated Lori’s mother. The romance appeared brief but was widely covered by celebrity media, as reported by Page Six.

5. Sarah Chapman

Sarah Chapman, the mother of one of Diddy’s daughters, maintained a more private relationship with the mogul. While their romantic ties were not as publicly discussed, they have co-parented amicably over the years.

6. Yung Miami (Caresha Brownlee)

Diddy was also linked to rapper Yung Miami of City Girls fame. Their relationship, though never officially defined, involved public displays of affection and frequent appearances together. Both described their dynamic as fun and supportive, suggesting a non-exclusive arrangement.

As Diddy navigates one of the most challenging periods of his life, his dating history — once celebrated in tabloids and entertainment headlines — is being reexamined through the lens of accountability. Each relationship tells a different story, but collectively, they form part of the broader narrative now unfolding in courtrooms and the public eye.