Who Has Diddy Dated? 11 Women Romantically Linked To The Mogul

Looking at Diddy's romantic connections and captivating love stories.

BYVictor Omega
diddy girlfriends

As a rap luminary, Diddy officially changed his name to "Love" in May 2022. Unsurprisingly, it's clear that this sentiment has guided much of his life. From an enduring relationship with the late Kim Porter to the likes of Jennifer Lopez and Lori Harvey, Diddy's affinity for romance and sensuality is undeniable and now he's found a new companion in Dana Tran, with whom he recently welcomed a baby girl named Love. Learn more about Diddy's most notable relationships and their lasting impact on his life. Here are Diddy Girlfriends.

11. Kim Porter

EAST HAMPTON, NY - SEPTEMBER 02: Host Sean "Diddy" Combs and Kim Porter with their twin daughters D'Lila Star Combs and Jessie James Combs pictured at "The Real White Party" presented by Sean "Diddy" Combs at the Combs' East Hampton estate on September 2, 2007 in East Hampton, New York. (Photo by Mat Szwajkos/CP/Getty Images for CP)

Observing her distinct Boheme-Georgia culture, Diddy was immediately captivated by Kim Porter in 1994. Intimidated by her grace and elegance, yet mesmerized by her beauty, he silently yearned for a relationship with her. Complemented with intelligence and poise, Kim was always unruffled and judicious in every situation — qualities that further enticed the Bad Boy CEO. However, despite this strong initial connection and sharing three children -- Christian, D'Lila Star, and Jessie James -- their romance wasn't sustainable, as Diddy began to pursue Jennifer Lopez in 1999. The couple rekindled the romance in 2003 before splitting for good in 2007.

10. Cameron Diaz

(L-R) Sean "Diddy" Combs and Cameron Diaz attend Tower Building on February 5, 2011 in Dallas, Texas.

In 2008, Cameron Diaz, one of Diddy's rumored girlfriends, briefly ignited a whirlwind romance regarded as merely a fleeting encounter between two era-defining stars. Six years later, when Us Weekly reported on Cameron's relationship with Benji Madden, Diddy allegedly quipped "If only I could turn back the clock", seemingly regretful of their supposed split.

9. Miracle Watts

LOS ANGELES, CA - AUGUST 22: Miracle Watts attends the Premiere Of TV One's "When Love Kills" at Harmony Gold on August 22, 2017 in Los Angeles, California. (Photo by Earl Gibson III/Getty Images)

Rumors of Diddy and Miracle Watts' relationship got a boost when the pair attended Diddy's New Year's Eve celebration. Seemingly confirming their romantic involvement, Watts later responded to a photo the hip-hop star shared of himself in the ocean with an affectionate comment, expressing her admiration for him by saying "GEEZ" along with love-struck emojis. Although not necessarily a confirmation, many believed that she became Diddy's latest girlfriend.

8. Misa Hylton Brim

NEW YORK - JANUARY 23: (L-R) Justin Dior Combs, Sean "Diddy" Combs and Misa Hilton attend Justin Dior Comb's 16th birthday party at M2 Ultra Lounge on January 23, 2010 in New York City. (Photo by Johnny Nunez/WireImage)

For two decades, Misa Hylton Brim and Diddy have worked together to nurture their son Justin Combs. Additionally, Misa has acted as an adoring "second mother" to his other kids, Niko and Madison, from other relationships. Upon learning of the tragic passing of Kim Porter, Combs' long-time partner, Hylton Brim penned a sorrowful tribute featured in PEOPLE Magazine: "I am simply unable to comprehend that you are no longer here," she wrote with profound sadness. Unfortunately, it appears that there could be some underlying issues regarding their co-parenting relationship following Misa's comments regarding their son's DUI arrest.

7. Sarah Chapman

BEVERLY HILLS, CA - JUNE 03: Sean Combs and Sarah Chapman attend the Ladylike Foundation's 9th Annual Women Of Excellence Awards Gala at The Beverly Hilton Hotel on June 3, 2017 in Beverly Hills, California. (Photo by Earl Gibson III/Getty Images)

Among Diddy girlfriends in the early 2000s, Sarah Chapman's union with Diddy was ephemeral yet profoundly significant. As a result, it ushered in the arrival of Chance Combs. Despite their amicable separation, Sarah harbored no ill will and recently commemorated Kim Porter's passing on Instagram, praising the late mother for her unwavering devotion to her children. "Rest assured Kim, that your young ones will be blessed with love and prayers. Your resilience shines through in your children's unbreakable bond," she wrote.

6. Jennifer Lopez

Sean "Puffy" Combs & Jennifer Lopez during The 42nd Annual GRAMMY Awards - Arista Records Pre-GRAMMY Party at Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by SGranitz/WireImage)

In 1999, Diddy and Jennifer Lopez had a tumultuous two-year relationship that made headlines. During their time together, Lopez credited Combs for being a source of mentorship. But on Valentine's Day 2001, the couple called it quits after the drama surrounding a nightclub shooting in late '99. Authorities arrested both of them. However, they were eventually absolved of any charges. Afterward, Lopez revealed she desired a different kind of family life than the one Diddy could provide her.

5. Lori Harvey

LOS ANGELES, CA - JUNE 02: Lori Harvey is seen on June 02, 2023 in Los Angeles, California. (Photo by thecelebrityfinder/Bauer-Griffin/GC Images)

In July 2019, Lori Harvey and Diddy made headlines for engaging in a brief yet highly-publicized relationship. Subsequently, the couple jetted off to Italy for a family vacation, only for Lori to unfollow the rapper on social media months later due to his being photographed with another woman.

Refuting popular belief, Lori recently set the record straight in an E! interview with Adrienne Bailon, where she affirmed that neither Diddy nor his son Justin Combs ever romanced her. Furthermore, she clarified that false accounts of passionate encounters with those she's never met have been circulated in the past, though she typically remains silent concerning such speculation.

4. Cassie Ventura

NEW YORK, NY - MAY 07: Cassie and Diddy "Heavenly Bodies: Fashion & the Catholic Imagination", the 2018 Costume Institute Benefit at Metropolitan Museum of Art on May 7, 2018 in New York City. (Photo by Taylor Hill/Getty Images)

In 2007, Cassie Ventura and Diddy began their on-again, off-again relationship that persisted for over a decade. Despite their attempts to remain discreet until 2012, the public discovered the union, though it eventually fizzled out in 2018 due to Diddy's lack of commitment. Four years later, he paid homage to his ex at the BET Awards Lifetime Achievement ceremony, despite having released a song about trying to move on from her. After their split, Cassie married Alex Fine in 2019 and they have two children.

3. Naomi Campbell

Sean "P. Diddy" Combs and Naomi Campbell during 2003 Clive Davis Pre-GRAMMY Party - Inside at The Regent Wall Street in New York City, New York, United States. (Photo by KMazur/WireImage)

As the 2001 British Vogue photo shoot indicated, for a brief period Diddy was linked to Naomi Campbell, widely hailed as one of the most beautiful women in the world. In 2002, rumors proliferated that their connection had developed into something more intimate. However, neither confirmed a romantic relationship. Nevertheless, the two have continued to maintain a strong friendship for nearly two decades, and have even made joint appearances on the red carpet up until 2022. Furthermore, during a holiday trip to St. Barts, Diddy sported a T-shirt with Campbell's face on it - a testament to the palpable bond between them.

2. Gina Huynh

LAS VEGAS, NEVADA - APRIL 02: Gina V Huynh attends the Pre-Grammy Brunch & Surf Club Label Launch Celebrating Hit-Boy at the Lavo Restaurant at The Palazzo Las Vegas on April 02, 2022 in Las Vegas, Nevada. (Photo by Johnny Nunez/WireImage)

In 2019, tabloid speculation linked Gina Huynh, a model based in Los Angeles, to P. Diddy. Then, after the Billboard Awards of 2022, Gina posted a photograph on her Instagram Story which showed her receiving a kiss on the cheek from the hip-hop mogul. This romantic gesture prompted an impassioned response from Yung Miami, who was then Diddy's partner, who wrote, "Somebody, please give this girl some attention!"

1. Yung Miami

US rappers Yung Miami (L) and Sean "Diddy" Combs arrive for the 2023 Met Gala at the Metropolitan Museum of Art on May 1, 2023, in New York. - The Gala raises money for the Metropolitan Museum of Art's Costume Institute. The Gala's 2023 theme is "Karl Lagerfeld: A Line of Beauty." (Photo by Angela WEISS / AFP) (Photo by ANGELA WEISS/AFP via Getty Images)

The list of Diddy Girlfriends wouldn't have been complete without Yung Miami. On June 9, 2022, Diddy divulged to Yung Miami, the host of the podcast Caresha Please, that he was single. He detailed, "We have dates, we're friends, and we explore exotic locations—it's great!" However, it was reported in April 2023 that the two had elected to sever their romantic relationship but still maintain a close bond. Miami elucidated their connection, saying: “We shared an incredibly strong and intimate connection. We did it all: spending every day together, him supporting me, me supporting him."

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