Infamous rapper and record producer, Sean Combs, also known as Puff ‘P’ Diddy, has been charged with many crimes. The first person to make these allegations and file a lawsuit was none other than his long-time on-and-off girlfriend, Cassandra ‘Cassie’ Ventura. As the case against the rapper continues in court, people are curious to know about the kind of relationships he had with other romantic partners. So, here’s a look at all the women that P Diddy has dated.
Diddy dated Misa Hylton and welcomed his first and only child with her
Diddy dated fashion designer, Misa Hylton before either of them had established their names in their respective fields. They were in a relationship in the early 1990s and also welcomed their only child together, Justin Combs, in 1993. However, the two broke up amicably after becoming parents. But their cordial bond soured when their son, Justin, was arrested for driving under the influence. Misa took to her Instagram Stories and blamed this on Diddy as he had become the face of the alcohol brand Ciroc in 2007. She accused him of promoting something very unhealthy. However, after this incident, the exes reconciled and became friends again.
Diddy cheated on Kim Porter while she was expecting twins
Diddy and model Kim Porter started dating soon after his breakup from Misa. The rapper became a dad for the second time when Kim gave birth to their son, Christian, in 1998. Diddy had also adopted Kim’s son, Quincy, from a previous relationship. The couple went on and off for a while after the birth of their son. In 2006, Kim and Diddy became parents to twins, D’Lila and Jessie. However, during this time, Diddy’s friend, Sarah Chapman, was also expecting his child. Kim opened up about the ordeal and stated:
“I would have preferred to find out from him because that’s a man. I know it’s hard for anyone to say to their significant other, ‘I’ve gotten into some s— and I got a baby on the way.’ But men do get caught up in things; I’m not naive to that. Still, there’s a right and a wrong way to handle it. Because, most of all, we were friends. Even if I couldn’t have understood it as a woman, I would have understood it as a friend.”
Kim called it quits with Diddy in 2007. However, they remained friends until she passed in 2018 from pneumonia. Diddy continued to be a father to her son, Quincy, whom he had adopted. The rapper would also post about Kim on her birthdays even after she passed away.
Diddy and Jennifer Lopez dated for two years, but the rapper cheated on her
Diddy had accompanied Jennifer Lopez as her boyfriend when she attended the 2000 Grammy Awards in her world-famous green Versace dress that led to the emergence of Google Images. They were in a relationship from 1999 to 2001, but broke up due to the rapper’s infidelity. Years later, in an interview with ET, Diddy called JLo one of his greatest loves.
Diddy and Cassie Ventura’s tumultuous relationship
Singer, Cassie Ventura and Diddy began dating in 2007 and were in an on-and-off relationship for a decade before finally breaking up in 2018. Cassie, who had signed with Diddy’s Bad Boy Records, was the first person to file a lawsuit against him in 2023. The complaint, as shared by People, alleged that Diddy had taken complete control of her life, and she had no choice but to comply out of fear.
Diddy welcomed his last child with Dana Tran
Diddy and model Dana Tran welcomed a daughter, Love, in 2022. Although parents to their daughter, it hasn’t been confirmed if Dana and the rapper ever dated. The news of his daughter’s birth was announced on X by Diddy himseld. 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! God is the Greatest!”
What are your thoughts on Diddy’s dating history? Let us know.
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