Diddy's Relationship History: The Hip-Hop Star's Famous Exes

The 'I'll Be Missing You' spitter, who was accused of rape, abuse and sex trafficking by his ex-girlfriend in a lawsuit, has dated a number of well-known women, some of which are actress and singer.

AceShowbiz - Being rich and famous, it's not hard for Sean "P. Diddy" Combs to find himself a girlfriend. Throughout his career, the hip-hop artist has been romantically linked to a string of beautiful ladies, including some famous stars. From model and fashion designer to actress and singer, the rapper has added them to his relationship history.

Some of the relationships resulted in his children, and some others gave birth to his hit songs such as "Must Be Love". While the "I'll Be Missing You" rapper managed to remain on good terms with a few of his former girlfriends, he was recently hit with sexual abuse allegations by one of his exes. In light of the lawsuit which also put the spotlight on his relationship history, AceShowbiz has listed a number of Diddy's famous exes.

1. Misa Hylton Brim

Misa Hylton Brim
Cover Images/Humberto Carreno

In the beginning of his career in the music industry, Diddy was in a romantic relationship with Misa Hylton Brim. The "Can't Nobody Hold Me Down" hitmaker, who is also known by his stage names Puffy and Puff Daddy, began his romance with the fashion designer in the early 1990s. At that time, the two also worked together as he hired her to style music group Jodeci, whose album and look he was in charge of.

In December 1993, Diddy and Misa welcomed their only child together, Justin Combs. Later on, it was reported that the two called it quits not long after Justin's birth. Though so, the two have committed to co-parenting their son, who gained international popularity through MTV's "My Super Sweet 16" in 2008.

2. Kim Porter

Kim Porter
Cover Images/David Wright

Diddy met Kim Porter for the first time at a studio. The "Been Around the World" rapper recalled in an interview that he admired "her lips, her eyes, her mouth, her shape" and "her energy" during their first meet-up. At that time, the model was in a romance with his music rival Al B. Sure, the father of her son Quincy Brown. In 1994, Diddy started dating Kim and even adopted Quincy later on.

A few years into their relationship, Diddy and Kim welcomed their first child, son Christian Combs, in April 1998 before breaking up one year later. The two reunited in 2003 and welcomed their twin daughters D'Lila and Jessie Combs in December 2006. However, before the twins' arrival, he cheated on Kim with her pal Sarah Chapman, who mothered yet another daughter, Chance Combs, for him. In July 2007, Diddy and Kim broke up for good. They remained friends until her death from lobar pneumonia in 2018.

3. Jennifer Lopez

Jennifer Lopez
Cover Images/BauerGriffin

Diddy was involved in a relationship with singer Jennifer Lopez for around two years. The "Victory" spitter and the "On the Floor" singer began their romance back in 1999. One year later, the two made a public appearance together at the 2000 Grammy Awards, where she went daring in an iconic green Versace dress.

Diddy and Jennifer decided to go their separate ways in 2001. He announced their split through his publicist in February of that year. On the reason behind the breakup, the songstress claimed in a chat with Vibe in 2003 that he cheated on her. In a 2019 interview on "The Breakfast Club" podcast, she recalled having "this kind of crazy, tumultuous relationship" with the "Come with Me" spitter "that ended in a bang."

4. Naomi Campbell

Naomi Campbell
Cover Images/Jason Mendez

After calling it quits with Jennifer, Diddy appeared to have moved on with British model Naomi Campbell. Diddy and Naomi were romantically linked for the first time back in 2001. At that time, the couple was pictured together for a British Vogue cover. It was believed that they had something more than a friendship one year later. However, they never confirmed their relationship.

Although it was reported that they later ended their romance, Diddy and Naomi have remained good friends since then. On November 9, 2023, the supermodel celebrated his 54th birthday by attending his party in London. They hung out together during the bash and were captured having a good time in some photos. However, she was believed to have distanced herself from the "Satisfy You" rapper following a sexual assault lawsuit by his other ex against him.

5. Cassie

Cover Images/Dario Alequin

Not long after his split from Kim, Diddy started dating fellow artist Cassie, whose real name is Cassandra Ventura. Despite starting their romance in 2007, the two did not go public with their relationship until 2012. They were in an on-again-off-again relationship until they called it quits for good in 2018. Having moved on from Diddy, she tied the knot with personal trainer Alex Fine in 2019. The wedded couple shares two children together.

On November 16, 2023, Cassie filed a lawsuit against Diddy and accused him of rape, abuse as well as sex trafficking, which all happened during their on-off relationship. The "Best Friend" rapper, through his attorney, vehemently denied the allegations, calling them "baseless and outrageous lies." Later on, the two agreed to settle the lawsuit. Though so, his attorney insisted that the settlement was not an "admission of wrongdoing" by his client.

6. Cameron Diaz

Cameron Diaz
Cover Images/Roger Wong

In 2008, Diddy reportedly met actress Cameron Diaz for the first time and began their on-off romance. That same year, the "Let's Get It" spitter and the "Charlie's Angels: Full Throttle" actress were photographed together at his "Operation Harlem 2 Hollywood" party. She could be seen wrapping one of her arms around his shoulder as they struck a pose together. They were believed to have separated for good in 2012.

Years later, in 2014, Diddy allegedly talked about his romance with Cameron when he was grabbing dinner. A source spilled to Us Weekly at the time, "He was at a dinner and the subject turned to Cameron dating Benji Madden. He said, 'If I could turn back time, things would be different!' He was bummed, saying, 'She's the sexiest girl in the world.' " The source was referring to Cameron's now-husband Benji, who started dating Cameron in 2014 and married her in 2015.

7. Lori Harvey

Lori Harvey
Cover Images/BG020/BauerGriffin

In his late 40s, Diddy was romantically linked to model Lori Harvey, who was only 22 years old at the time. The "Diddy" spitter and the entrepreneur, who was adopted by comedian Steve Harvey, sparked romance rumors in July 2019 after being spotted strolling around the SoHo neighborhood in New York City together. One month later, they were caught on camera during their trip to Italy with her father Steve and mother Marjorie Harvey.

In addition to the Big Apple and Italy, Diddy and Lori were seen together in Mexico. The "Bad Boy for Life" rapper and the SKN founder were believed to have gone their separate ways in October that same year after she unfollowed him on Instagram and he was caught grabbing dinner with another woman. However, the two never publicly confirmed their relationship.

8. Yung Miami

Yung Miami

Diddy sparked romance rumors with fellow rapper Yung Miami in 2021. The "I Need a Girl (Part One)" spitter and the City Girls raptress confirmed in June 2022 that they were in an open relationship. However, she revealed that they have called it quits in April. Speaking to The Cut at that time, she said, "We're still friends! We're still good friends! But we're single. That's not my man."

Though so, Diddy and Miami apparently remain on good terms. Recently, the 29-year-old raptress paid a sweet tribute to the "Shake Ya Tailfeather" rapper on his 54th birthday. Making use of Instagram, she uploaded a series of photos, including ones from their vacation in Paris, France. Along with the snaps, she exclaimed, "Happy birthday @diddy There's no other place I'd rather be! I love to rock with you," adding a white heart emoji.

You can share this post!

You might also like
Related Posts