His Romantic Journey from Jennifer Lopez to Cassie Ventura in Hollywood Life
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“See, Diddy is my nickname. Love is my real name. I just changed my name to Love,” the man born Sean Combs said during his final appearance on The Ellen DeGeneres Show in May 2022. “Sean Love Combs, that’s what it says on my driver’s license, that’s my official name, Love.” Although the rapper was recently arrested in New York on Monday, September 16, and charged with racketeering, sex trafficking, and transporting individuals for prostitution, the hip-hop icon and spirits connoisseur has had a life filled with romance and sensuality, involving a long list of women over the years. Though Kim Porter will always have a special place in Diddy’s soul, he was romantically liked to other famous women like Jennifer Lopez, Lori Harvey, Yung Miami, and more.
But apparently, his dating history hasn’t been without drama. In November of 2023, Cassie accused the rapper of a string of alleged offenses, including claims of rape and other abuses. Although the case was reportedly settled, Diddy has been accused of sexual assault by multiple women and was taken into custody by federal agents in September 2024, following raids on his homes in March earlier that year. Here’s what to know about each of his most notable romantic relationships.
Kim Porter
Sean Combs began dating Kim Porter in 1994. “The first time I saw her, she was at the studio with her ex-boyfriend,” Diddy told Essence, referring to singer Al B. Sure, the father of Kim’s oldest child, Quincy. “I wasn’t trying to holler at her or anything, but I was admiring her—her lips, her eyes, her mouth, her shape, her energy—and thinking, ‘I wish I had a girl like that.’”
She kind of made me nervous,” he told Essence. “She wasn’t like a New York girl. She was Bohemian, mixed with Georgia-peach hospitality. I got the idea she’d like doing stuff like walking barefoot in the grass. I didn’t think I could get her to like me. She was smooth, you know, like ice. She’s cool and collected and thinks before she speaks. You meet a lot of young ladies, and they just don’t do that. Kim was never pressed; she was always in control.”
While Kim was in control, Diddy wasn’t always in control of his love. Kim and Diddy split in 1999, as he began seeing Jennifer Lopez. The two rekindled their love in 2003, before splitting for good in 2007.
During their time together, Diddy and Kim started a family. They welcomed Christian “King” Combs in 1998 and twin daughters D’Lila Star and Jessie James Combs in 2006. Diddy would also help raise Quincy, eventually adopting the boy as his son.
Tragically, Kim passed away in 2018 at the age of 46. She died in her sleep from lobar pneumonia.
Misa Hylton Brim
Misa Hylton Brim is a designer and stylist credited with putting together some incredible looks from the 1990s, per Capital XTRA. She is also known as Diddy’s high school sweetheart and the mother of his son, Justin Combs. Misa and Diddy welcomed Justin in 1993. Since then, they have co-parented their son together.
“Kim, for the last 20 years we have raised our children together, my mind cannot begin to wrap around the fact that you are not going to be here,” Misa wrote following Porter’s death, per PEOPLE. “Thank you for being a 2nd mother to Justin and for loving Niko and Madison just the same,” she added, referring to her children from another relationship.
Sarah Chapman
Diddy had a brief romance with Sarah Chapman in the early 2000s. It was long enough for them to welcome a daughter, Chance Combs, who was born shortly before twins D’Lila and Jessie. The romance didn’t last much longer after Chance’s birth, though Sarah didn’t seem to hold any ill will. When Kim Porter passed away, she too mourned the loss.
“Rest in paradise Kim, and know your kids are covered in prayer and love,” she wrote on Instagram, per PEOPLE. “Your light will always shine thru your children and the way they all love each other is a blessing beyond words.”
Jennifer Lopez
One of the highest-profile romances of the late ’90s/early 2000s was that of Sean Combs and Jennifer Lopez. In 1999, Sean began dating J.Lo (while he was still with Kim, which triggered the split.) J.Lo and Diddy stayed together for two years,
“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,”