Who Is Diddy Girlfriend? Who Has Sean ‘diddy’ Combs Dated and Worked with Over the Years?

Sean “Diddy” Combs has been one of the most connected figures in entertainment for more than three decades. His partners span a wide range: high-profile romances that played out in the tabloids, a long-term relationship that became the center of his criminal trial, and business alliances that built and sometimes shattered his empire.

This is a breakdown of the key romantic and business partners in Combs’ life.

Misa Hylton

Misa Hylton was Combs’ girlfriend in the early 1990s, when he was working his way up at Uptown Records. Hylton was a fashion stylist who helped shape the looks of artists like Mary J. Blige and Jodeci.

The pair welcomed their only child, Justin Dior Combs, on December 30, 1993. They split shortly after Justin’s birth. Hylton later said Combs wasn’t ready to settle down so early in his career, but the two remained friendly while co-parenting their son. Hylton married JoJo Brim in 1995 and had two more children before that marriage ended in 1999.

Kim Porter

Kim Porter was Combs’ most significant romantic partner and the mother of four of his children. They began dating in the 1990s and had an on-again, off-again relationship for more than a decade.

Their son Christian was born on April 1, 1998. Combs also adopted Porter’s son from a previous relationship, Quincy Brown. In 2006, Porter became pregnant with twins, D’Lila Star and Jessie James, but before she gave birth that December, she discovered Combs was expecting a child with Sarah Chapman.

Porter ended the relationship for good in July 2007. Despite the split, the two remained close friends until Porter’s death in November 2018 from lobar pneumonia at age 47.

Jennifer Lopez

Combs dated Jennifer Lopez from 1999 to 2001, a period that coincided with his rise as a public figure beyond music. The relationship ended with Lopez citing infidelity. In a 2003 interview with Vibe, she said: “I never caught him [cheating], but I just knew. He’d say he was going to a club for a couple of hours and then never came back that night.”

Combs has called Lopez “without a doubt” one of his greatest loves. The two remained friendly after their split.

Cassie Ventura

Combs’ relationship with singer Cassie Ventura lasted nearly a decade, from 2007 to 2018. She was signed to Bad Boy Records when she was 19 and he was 37. Their on-again, off-again relationship ended in 2018.

In November 2023, Cassie filed a lawsuit accusing Combs of rape and repeated physical abuse over the course of their relationship. The lawsuit alleged that he had “complete control” over her life and that she feared retaliation if she denied him. The case settled out of court within one day. Combs denied all allegations of wrongdoing.

Cassie testified during Combs’ 2025 federal trial. She has since moved abroad with her husband, personal trainer Alex Fine, and their children.

Yung Miami

Combs was linked to City Girls rapper Yung Miami beginning in 2021. They confirmed their relationship in June 2022 and attended the Met Gala together in 2023.

Combs described their arrangement in a 2022 interview: “We’re dating. We go on dates. We’re friends. We go to exotic locations. We have great times.” Yung Miami later clarified that they were not exclusive. The relationship was part of the period when Combs was also expecting a child with Dana Tran.

Sarah Chapman

Sarah Chapman is a businesswoman and longtime friend of Combs. They never publicly dated, but they welcomed a daughter, Chance Combs, in July 2006, while Combs was still in a relationship with Kim Porter.

Chapman has largely stayed out of the public eye. She attended Combs’ trial proceedings in 2025.

Dana Tran

Dana Tran is a cybersecurity professional and model who welcomed Combs’ seventh child, Love Sean Combs, on October 15, 2022. The two never confirmed a romantic relationship, but they have been seen co-parenting. Combs announced Love’s birth in December 2022, writing that he was “so blessed.”

Kirk Burrowes: The Business Partner Who Sued

Kirk Burrowes co-founded Bad Boy Entertainment with Combs in 1993. He served as the label’s president and chief operating officer. Combs allegedly gave his mother Janice 75% of the company and Burrowes 25%, according to Burrowes’ later claims.

In February 2025, Burrowes filed a lawsuit accusing Combs of years of sexual harassment, physical aggression, and forced compliance with degrading sexual acts. The complaint alleged that Combs groped him, forced him to witness sexual acts in the office, and in 1995 restrained him in an apartment and simulated intercourse until he ejaculated.

Burrowes also alleged that in 1996, Combs burst into his office with a baseball bat and forced him to sign over his 25% stake in Bad Boy Entertainment. He claimed Combs later blacklisted him from the industry.

Combs’ legal team denied the allegations, calling the lawsuit “another frivolous attempt to re-litigate claims that have been repeatedly thrown out of court over the past 30 years.”

Diageo: The Liquor Partnership That Ended

Combs’ most lucrative business partnership was with Diageo, the liquor giant behind Cîroc vodka and DeLeón tequila. The relationship ended in January 2024 after lawsuits were settled.

As part of the resolution, Diageo acquired the remaining 50% of DeLeón in a transaction valued at approximately $223 million. Combs no longer has any business relationship with either brand.

Current Status

Combs is currently serving a 50-month federal prison sentence at FCI Fort Dix in New Jersey. He was convicted in July 2025 on two counts of transportation to engage in prostitution. His projected release date is March 2, 2028.

His legal team is appealing the conviction. Combs has remained focused on his defense while incarcerated, with his lawyer describing him as having become “like a paralegal” in studying his own case.