Diddy dating history: From Jennifer Lopez to Lori Harvey

7 December 2023, 12:26 | Updated: 26 March 2024, 14:23

Diddy dating history: From Jennifer Lopez to Lori Harvey
Diddy dating history: From Jennifer Lopez to Lori Harvey. Picture: Getty

Who is Diddy dating? Who are his ex-girlfriends and is he currently dating anyone in 2024?

Sean 'Diddy' Combs is a rapper, actor, producer and record executive, who also goes by the monikers P Diddy and Puff Daddy.

The 54-year-old has has a string of relationships with various women, including Cassie, Lori Harvey and Yung Miami.

His ex-girlfriend Cassie, along with three others, filed a lawsuit in 2023 accusing Diddy of abuse and sexual assault. But, who is Diddy currently dating and who are his ex-girlfriends?

Sean "Diddy" Combs"  is an American rapper, producer, record executive and entrepreneur.
Sean "Diddy" Combs" is an American rapper, producer, record executive and entrepreneur. Picture: Getty
  1. Yung Miami - Caresha Browlee

    The City Girls member, 30, and Sean “Diddy” Combs went public with their romance in June 2022, but made it known that it was not a monogamous relationship.

    The 30-year-old, whose real name is Caresha Brownlee, said she and Diddy, 54, “had our own situation” and refused to label their romance.

    “We were f–king with each other hard. We were together every day at one point,” she said. “He supported me, I supported him. I’ll let the internet call it whatever they want to call it.”

    Yung Miami and Diddy perform onstage at the 2023 MTV Video Music Awards held at Prudential Center on September 12, 2023 in Newark, New Jersey.
    Yung Miami and Diddy perform onstage at the 2023 MTV Video Music Awards held at Prudential Center on September 12, 2023 in Newark, New Jersey. Picture: Getty
  2. Miracle Watts

    Miracle Watts
    Miracle Watts. Picture: Getty

    Diddy and Miracle Watts had been rumoured to be dating since they were spotted together at Diddy's New Years Eve Party.

    Watts seemingly confirmed their romance on a recent post Diddy uploaded of himself.

    The hip-hop mogul shared a photo of himself taking a dip in the ocean, with the caption,“Welcome to the LOVE ERA.”

    The model left a comment on the post, letting fans know she is feeling Diddy.

    She wrote “GEEZ” alongside heart-eye emojis on Diddy's snap.

  3. Lori Harvey

    Lori Harvey
    Lori Harvey. Picture: Getty

    Diddy and Lori Harvey sparked dating rumours in July 2019, after they were spotted together several times in Italy, Mexico, New York City and Atlanta.

    Lori was spotted with her arm around Diddy during a dinner in Nerano, Italy with Lori's stepfather, Steve Harvey.

    Diddy's son, Christian Combs, opened up about his father's relationship with Lori,saying: "They [are] good. They’re just being … Private time... That’s up to them."

    While Diddy nor Lori never publicly confirmed their relationship, it's believed they split up in October 2019.

  4. Gina Huynh

    Gina Huynh
    Gina Huynh. Picture: Instagram

    Rumours began swirling that Diddy was dating Gina Huynh in October 2018.

    The pair were pictured on a date with each other in July 2019.

    However, Diddy was pictured with his ex-flame Cassie, whom he had split with, in September 2019.

    Things turned left for Diddy and Gina. In an Jun 2019 interview with Tasha K, Gina alleged that Diddy physically abused her and made paid her $50,000 to get rid of her pregnancy not once, but twice.

  5. Cassie Ventura

    Cassie Ventura and Diddy
    Cassie Ventura and Diddy. Picture: Getty

    Diddy and Cassie were has an on-and-off relationship for over 10 years.

    The pair secretly began dating in 2007, and officially confirmed their relationship in 2012.

    In 2014, the pair were rumoured to be married after Cassie was spotted wearing a ring.

    Throughout 2015 until 2018, the pair were rumoured to have broken up and got back together.

    However, the pair officially split for the last time in October 2018, following reports that Diddy was hesitant on settling down with Cassie.

    Cassie has filed a lawsuit in 2023, which depicted Combs as an erratic, controlling individual with violent tendencies aimed at Ventura and others.

  6. Kim Porter

    Kim Porter and Diddy
    Kim Porter and Diddy. Picture: Getty

    Diddy and Kim Porter began dating in the ’90s and welcomed their first child together in 1998 — a son named Christian Casey.

    In 1999, the pair broke up in and had a legal battle in court over child support for Christian.

    Diddy then went on to date Jennifer Lopez for two years before he and Porter reconciled in 2003.

    In December 2006, they welcomed twin daughters D’Lila Star and Jessie James.

    Porter was also mother her son with music producer Al B, named Quincy Brown. When Quincy was only 3 years old, Combs became close to him and raised him.

    Combs and Porter split for the final time in 2007.

    Kim Porter sadly passed away from pneumonia in November, 2018.

  7. Cameron Diaz

    Cameron Diaz and Diddy
    Cameron Diaz and Diddy. Picture: Getty

    Diddy first hooked up with actress Cameron Diaz in 2008.

    In 2012, the Annie film star was spotted straddling Diddy at a CAA gala in West Hollywood.

    Shortly after, the pair had called off their fling.

  8. Jennifer Lopez

    Jennifer Lopez and Diddy
    Jennifer Lopez and Diddy. Picture: Getty

    Diddy and Jennifer Lopez began dating in 1999, whilst he was still in a relationship with Kim Porter.

    In a recent interview with The Breakfast Club, Jennifer Lopez opened up about her relationship with Diddy.

    “The Puffy era was just kind of a crazy, heightened time in my life. You know, Puffy and I both grew up in the Bronx,” she began and explained what the initial attraction was.

    “He had been in the music business and had all this success; I was just starting and making my first album when I met him."

    He became kind of a mentor to me in that moment. We had this kind of crazy, tumultuous relationship that ended in a bang.”

    The pair officially ended in February 2001.

  9. Sarah Chapman

    Diddy and Sarah Chapman
    Diddy and Sarah Chapman. Picture: Getty

    Although most of Diddy’s kids came from his relationship with Porter, he also had two other baby mommas between the ‘90s and ‘00s.

    The more recent of these was Sarah Chapman, who gave birth to his daughter, Chance, several months before Kim welcomed his twins.

    The pair’s relationship ended up falling apart for good just a few months later.

  10. Misa Hylton Brim

    Diddy and Misa Hylton Brim
    Diddy and Misa Hylton Brim. Picture: Getty

    Diddy and Misa Hylton-Brim welcomed their son Justin Combs in 1993, just a few months after they began dating.

    She’s best known as a hip-hop stylist, putting together some of the most iconic looks from the 90's.

    Although the pair ended shortly after conceiving Justin, they have remained amicable friends and co-parent Justin well.

  11. Naomi Campbell

    Diddy and Naomi Campbell
    Diddy and Naomi Campbell. Picture: Getty

    Diddy and Naomi Campbell sparked dating rumours after they were pictured together on British Vogue in 2001.

    It was evident the pair had an unmatched connection and supposedly turned romantic back in 2002.

    However, neither of them commented on the status of their relationship.

    The pair remained friends after their split.

Here Are All The Ways You Can Listen To Capital XTRA