“Diddy is my nickname. Love is my real name. I just changed my name to Love,” stated Sean Combs during his final visit to 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.” However, the rapper, who was detained in New York on September 16, 2024, facing charges related to racketeering, sex trafficking, and transportation for prostitution, exhibits a more complex side beyond his affectionate persona.
Throughout the years, Diddy has been associated with numerous partners, but the mounting allegations have unveiled a darker aspect of his life of “love.”
Diddy has frequently asserted that his late ex-partner Kim Porter would always occupy a special place in his heart. However, since her passing in 2018, allegations regarding his sexual history and purported misconduct have surfaced. His romantic history also includes relationships with high-profile figures such as Jennifer Lopez, Lori Harvey, and Yung Miami, although it has not been without its share of controversy. In November 2023, Cassie Ventura alleged a series of abusive behaviors against Diddy, making claims of rape and other offenses. Even though the case was settled, security footage emerged that showed him kicking Cassie in a Los Angeles hotel in 2016. Following these events, Diddy faced multiple accusations of sexual assault and was taken into custody by federal agents in September 2024, after his homes were reportedly searched.
Here’s an overview of Diddy’s most significant romantic relationships.
Kim Porter
Diddy’s relationship with Kim Porter began in 1994. “The first time I saw her, she was at the studio with her ex-boyfriend,” Diddy recalled, referring to singer Al B. Sure, who is also the father of Kim’s oldest child, Quincy Taylor Brown. “I wasn’t trying to hit on her or anything, but I was captivated by her beauty and energy, thinking, ‘I wish I had a girl like that.’
“She made me nervous,” he continued. “She wasn’t your typical New York girl. She had a unique Bohemian vibe that made her stand out. I thought she would enjoy things like walking barefoot in the grass, and I didn’t think I could get her to like me. Kim always exuded confidence and control that was distinct.”
While Kim was composed, Diddy often struggled to maintain stability in their romance. The couple separated in 1999 when Diddy began seeing Lopez, but they rekindled their relationship in 2003 before ultimately parting ways in 2007.
During their time together, Diddy and Kim built a family. They welcomed their son, Christian Combs, in 1998 and twin daughters D’Lila Star and Jessie James Combs in 2006. Diddy also played a fatherly role to Quincy, eventually adopting him.
Tragically, Kim passed away in 2018 at the age of 46 due to complications from lobar pneumonia.
Misa Hylton Brim
Misa Hylton Brim, a renowned stylist and designer recognized for her iconic 90s looks, is also known as Diddy’s high school sweetheart. Misa and Diddy welcomed their son, Justin Combs, in 1993, and they have co-parented him ever since.
“Kim, for the past 20 years we raised our children together, and it’s hard to grasp that you are no longer here,” Misa expressed after Kim’s death. “I appreciate everything you did for Justin and your love for Niko and Madison.”
Sarah Chapman
Diddy had a brief involvement with Sarah Chapman in the early 2000s. This relationship resulted in the birth of their daughter, Chance Combs, shortly before the arrival of twins D’Lila and Jessie. The romance was short-lived, but Sarah held no animosity toward Diddy. After Kim’s passing, she mourned Kim’s loss publicly.
“Rest in paradise, Kim. Your children are surrounded by love and prayers,” Sarah wrote on Instagram.
Jennifer Lopez
One of the most notable relationships of the late ’90s and early 2000s was between Sean Combs and Jennifer Lopez. They began dating in 1999 while he was still involved with Kim, which ultimately led to Kim and Sean’s breakup. J.Lo and Diddy maintained their relationship for two years.
“The Puffy era was a whirlwind in my life. Both of us grew up in the Bronx,” Jennifer recounted in a 2019 interview. “Puffy had already experienced a level of success in the music industry, and I was just starting my first album when we met. It was a tumultuous relationship that seemed essential for my growth as an artist.”
The couple publicly announced their separation on Valentine’s Day in 2001. “Mr. Combs confirms the breakup,” his publicist stated, urging respect for their privacy during this difficult time.
Jennifer later mentioned that she felt unable to achieve the family life she desired with Sean, noting the drama from the nightclub shooting incident in December 1999 that resulted in both of them being arrested, though they were later exonerated.
Naomi Campbell
Diddy was romantically linked to the supermodel Naomi Campbell in the early 2000s, sparked by rumors and their appearances in British Vogue. Their relationship is rumored to have blossomed around 2002, though the two never officially confirmed it, maintaining a platonic friendship after their speculated romance ended.
Cassie
Cassie Ventura’s romance with Diddy began in 2007 and was characterized by a tumultuous relationship that became public in 2012. The couple’s relationship endured until they separated in 2018, reportedly due to Diddy’s hesitance to commit further.
Following their breakup, Cassie married Alex Fine in 2019 and started a family. However, in November 2023, she filed a lawsuit against Diddy, alleging severe complaints including rape and physical abuse throughout their relationship. In her statement, Cassie emphasized her intention to speak out for herself and other women who face violence in their relationships.
Diddy’s legal team responded vehemently denying the allegations, asserting that Cassie’s lawsuit was an act of blackmail against him.
Cameron Diaz
Diddy briefly dated Cameron Diaz in 2008. Years later, in 2014, he expressed regret over their romance, suggesting that if given the chance, things could have been different.
Lori Harvey
Diddy’s relationship with Lori Harvey, the daughter of comedian Steve Harvey, sparked dating rumors in July 2019 when they were spotted together. Their unconfirmed romance included a vacation to Italy, but it didn’t last long, as Lori ceased following Diddy online in October of the same year.
Gina Huynh
Model Gina Huynh was linked to Diddy in 2019. In 2022, she reignited dating rumors by posting a photo on her Instagram, leading to public reactions from Yung Miami, who criticized Huynh for seeking attention.
Yung Miami
Despite claiming to be single, Diddy confirmed that he was dating Yung Miami in 2022 and described their relationship as fun and supportive. However, in April 2023, they acknowledged that their romance had ended but maintained their friendship.
Yung Miami shared candid details about their intense relationship in a subsequent interview, emphasizing their strong connection during their time together.
If you or someone you know has been sexually abused, please reach out to the National Sexual Assault Hotline at 1-800-656-HOPE (4673) for confidential support.
If you or anyone you know is facing domestic violence, reach out to the National Domestic Violence Hotline at 1-800-799-7233 for assistance.
