P Diddy, AKA Sean Combs, AKA Puff Daddy is a rapper, record producer and actor who’s been in the industry for a number of years now. Whilst Homeland Security are busy looking for Combs right now we’ve decided to get busy looking into his dating history.
Diddy has a long list of exes ranging from A-list musicians to A-list actors. Whilst some of these relationships were short lived, others have lasted years, with the rapper having seven children with four different women. Whilst there’s been rumors and speculation surrounding some of these relationships, we want to mainly focus on the ones that have been confirmed, although we’ll touch on some of those rumored relationships at the end.
Misa Hylton
Hylton is a designer and stylist who was Diddy’s high school sweetheart; the pair were together for a few years between 1992 and 1995, when he was still a relatively fresh face in the music scene. Hylton is also the mother of the rapper’s eldest son, Justin Combs, who was born in 1993; last year, when Justin was arrested driving under the influence, Misa placed the blame for the DUI on Diddy, making several cryptic posts alluding to the rapper via Instagram. Despite this, the pair were not at odds for long, as it appeared that they were on good terms again, according to People.
Kim Porter
Diddy’s relationship with Kim Porter was by far the longest lasting relationship out of all of them. They started dating in the nineties and had their first child, Christian, in 1998. They split up not too long after Christian’s birth, and the pair ended up battling against each other in court for custody over their son. The pair would be on again off again for a number of years until sometime around 2007, when they split for good.
Just before their final split, Porter would find herself pregnant with Diddy’s twins, D’Lila Star and Jessie James. Unbeknownst to her, Diddy had also gotten another woman, Sarah Chapman pregnant around the same time. He eventually owned up to his infidelity, but Porter had already found out at that point.
The two remained pretty close friends until Porter’s untimely death in 2018 due to Lobar Pneumonia. In a video posted by E! News on the fourth anniversary of her death, Diddy gave a heartfelt tribute, “You made me a better father and a better man. I’m so grateful for all the moments, the memories, the laughs, and the love.”
Jennifer Lopez
During one of the gaps when Diddy wasn’t seeing Kim Porter, he dated singer, actor, dancer Jennifer Lopez. They began dating in 1999 and stayed together for two years before breaking things off. Lopez claimed that infidelity was ultimately what destroyed their relationship, according to Instyle. However, the two remained friends, and Diddy went on to claim that Lopez was “without a doubt” one of his great loves.
Sarah Chapman
Diddy had another brief fling with businesswoman Sarah Chapman. Although it didn’t last long, it was just long enough for the two to welcome a child together — this was still at a time before Diddy had permanently broken up with Kim Porter.
Cameron Diaz
Although this was seemingly only a short term fling sometime around 2008, it’s still worth mentioning, especially because it evidently left an impression on Diddy. According to an article from US Weekly in 2014, the rapper reportedly missed his fling with Diaz telling Benji Madden, “if I could turn back time, things would be different.”
Cassie Ventura
In 2007, after Kim Porter and Diddy broke things off for good, the musician started dating Cassie Ventura. In the beginning it was all hush hush, keeping their relationship a secret before confirming the rumors in 2012. Like many of Diddy’s relationships, they were on again, off again, and in 2014 people even began speculating that they were married, as Cassie was spotted wearing a ring, according to the Economic Times. Neither of them acknowledged the engagement, and next thing you know, rumors were spreading that they had broken up.
The pair managed to make it last until 2018, when they called it quits for good. Unlike Diddy’s previous exes, the two did not remain on good terms — last year, People reported that Cassie had accused the musician of raping and abusing her during their relationship. Cassie filed a lawsuit against Diddy which was settled in November, and no details about the settlement have been made public.
Gina Huynh
Towards the end of his relationship with Cassie, Diddy began seeing model Gina Huynh. The pair were spotted on a date in 2019. Huynh also made claims of abuse against the musician in 2023; according to Page Six, he stomped on her stomach, and punched her in the back of the head. He also allegedly paid her $5,000 to have an abortion.
Yung Miami
Rumors began circulating in 2021 that Diddy and City Girls rapper Yung Miami were dating, but the pair didn’t confirm anything until the following year. Appearing on the music podcast Caresha Please hosted by Yung Miami, Diddy confirmed to all viewing that the two were in fact dating. Medium.com cites various sources who claim the couple decided to end their relationship in November 2023.
Dana Tran
It’s difficult to keep track of the relationship timeline between Diddy and Dana Tran; whilst the rapper never confirmed that they were dating, they did welcome a child, Love Sean Combs, together in 2022 with the musician making the announcement on X (formerly Twitter). This came after his appearance on Yung Miami’s podcast.
Unconfirmed ex-girlfriends
Whilst the above names are relationships that we know happened, there are a few people who many suspected Diddy of dating that were never fully confirmed. So while the women below have been speculated about, they’re not official exes.
Naomi Campbell
For a brief period in the early 2000’s the record producer was linked to English model Naomi Campbell; the pair were photographed together in British Vogue in 2001, but neither of them ever spoke on whether they were a couple.
Lori Harvey
Steve Harvey’s daughter, Lori Harvey, is another name that is often linked to the star. Rumors of romance started in 2019, and the pair were seen holidaying together in Italy. Prior to these rumors, Harvey had previously been linked to Diddy’s son, Justin Combs. In the end, Harvey shut down the rumors that she ever dated Diddy, according to People.
Miracle Watts
Last but not least, Diddy was rumored to be dating Instagram model Miracle Watts in 2021. The pair had been spotted together at a New Year’s Eve party, but that’s all there was to go off on that one.
