Source: Courtesy / Combs Enterprises
Sean Combs affectionately known as Puff Daddy and also P. Diddy and also Diddy and more recently Brother Love, recently received a BET Lifetime Achievement Award for his contribution to music. During his acceptance speech on June 26, the music mogul, producer, CEO and master of urban marketing, took a moment to thank the most influential people in his life. Combs gave personal shout outs to notable women he’s dated in the past. On the sidelines, his rumored boo Yung Miami cheered him on. The sassy half of City Girls held a red poster board that read “Go Papi.” Caresha Brownlee cheered like the ultimate fan. The “Twerkalator” is not the first woman to be swept into a situationship with the mogul.
Combs, 52, has never been married, though, he’s had multiple long term relationships and multiple name changes over the years, he’s never given a woman his last name. As an extrovert, Brother Love has been public about some of his love affairs and has shared a glimpse into his private life. One thing about Diddy is he keeps a baddie. MADAMENOIRE takes a look at a few of the most notable Diddy dames.
Misa Hylton
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Misa Hylton is the genesis. She is the mother to Puff Daddy’s eldest son, Justin Dior Combs. At 17-years-old, Hylton made a cameo in Notorious BIG’s, “Big Poppa” video, sipping champagne with Puff in a hot tub. Her close proximity to hip hop and R&B fostered close relationships with some of the genres’ largest icons. Those relationships budded into friendships that led to Hylton’s thriving career as a stylist. If Puff shaped the sound of the 1990s with his remixes, then Hylton shaped the hip hop fashion with her style sense. She’s credited for styling Mary J. Blige, Jodeci, and Foxy Brown. One of Lil Kim’s most iconic looks was conceived by Hylton – the iconic blue pasty ensemble. By the mid-90s Hylton and Puffy’s relationship had ended. She continues to style notable artists and has worked with the Carters on their “ApeShit” video and The City Girls’ “Twerkalator.” Hylton also owns the Misa Hylton Fashion academy.
Kim Porter
Source: Ken McCoy / WENN / WENN
Porter began dating Puffy Daddy in the ‘90s, as well. As a stunning model, Porter kept men’s necks on a swivel. She dated the OG light-skinned king, Al B. Sure with whom she shared her first son Quincy. Porter continued her modeling career and dabbled in acting during her and Puffy’s relationship run. Together she and the “Benjamins” rapper had three children Christian, Jessie James, and D’Lila Combs. Combs also assumed the role of fathering Quincy. Porter and Puff Daddy’s relationship ran hot and cold over the course of ten years until calling it quits for good in 2008. They remained friends until her death at the age of 47 in 2018.
Jennifer Lopez
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Many fans give Jennifer Lopez and Puff’s relationship a side-eye. For decades, rumor has it this relationship was a PR stunt to raise each artists’ profile. Jenny from the block began dating Diddy as her music career began to kick off. The Selena actress wanted to flex her wings as a pop artist. Puffy served as a mentor for the singer. For some time, the pair were joined at the hip, till the relationship ended in early 2001 after the infamous nightclub shooting in New York City.
Sarah Chapman
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Sarah Chapman gave birth to Diddy’s third child, Chance Combs, five months before the birth of his twins with Kim Porter. The timeline is murky to say the least. Nonetheless, Chapman was romantically involved with the rapper. Working behind the scenes in the fashion industry, Chapman has never taken the spotlight. She is an active participant on social media with over 200,000 followers on instagram. She can be seen traveling the world and supporting both her daughter Chance and the Combs Twins’s modeling careers.
Cassie
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Deja-Vu. The public first became aware of Cassie when she dropped her single “Me & You” in 2007. Around the same time, Diddy had his eye on the singer. He signed her to be a spokesperson for his Sean Jean apparel line. The two began dating secretly in 2007. They began making public appearances together in 2012. Back in 2013, she spoke with MN about her relationship with the mogul: ”Just being around him is a completely inspiring experience.”
Cassie continued to release music during their relationship, but her career never really found its footing after the initial success. In 2018, after many break-ups and make-ups, Diddy and Cassie ended their relationship. Within a year, she would be happily-married to her trainer Alex Fine. Mr. and Mrs. Fine have two children together.
Yung Miami
Prince Williams
Sassy City Girl Yung Miami is the latest baddie to fall into an entanglement with Brother Love. The two have been hand-holding and Diddy-boppin around the town. Yung Miami didn’t play the background long. Her refusal to be lowkey is hilarious. On the inaugural episode of her Revolt podcast Caresha Please, the feisty rapper interviews Brother Love. When he says that their relationship status is “friends,” she insists they go together—“real bad.” The Miami rapper has no problem fighting for her man. Recently, She engaged in a social media sparring match with another of Brother Love’s friends, Gina Hunyh.
The Combs Girls
Source: Gregg DeGuire / Getty
As mentioned, Brother Love fathered three daughters with previous partners, Chapman and Porter. Jesse James, D’Lila and Chance are the last in the Combs Clan. Each 15-year-old teenager is navigating high school and budding modeling careers. The Combs girls began their modeling careers at 7-years-old, walking the runway for the Swarovski and Ooh, during New York fashion week in 2013. The trio continue to navigate the industry and turn heads with their beauty and style. Their most recent Vogue shoot with their famous father turned heads. The ladies showed off their modeling prowess. They are no longer just bouncing along the catwalk or posing with toothy grins. The sisters served fierce poses, over the top hair and intense model faces. The future is bright for all three baby girls.
Mama Combs
Prince Williams
Janice Combs, often called Mama Combs, is the 82 year-old queen of Sean Combs’ life. His relationships with women may be rocky, but his love for Mama Combs knows no bounds. Ms. Combs embodies style, grace and opulence. Her signature blonde hair is attention grabbing as is her drip. For her 80th birthday in 2020, Combs penned a sweet message for his Mama, attributing his greatness to Mama Combs. The Bad Boy honcho presented his mother with a $1 million check and a brand new Bentley.
