In addition to his notoriously wild parties, Diddy also has a complicated love life. The rapper once dated Jennifer Lopez, had an on-again, off-again relationship with Kim Porter, dated many women and had a child with a Vietnamese-American beauty.

As the most notorious “playboy” in the American music industry, Diddy (real name: Sean Combs) not only shocked with his decadent parties but also constantly caused controversy with his tumultuous love affairs. The rapper, born in 1969, has dated many people, from showbiz beauties to beauties outside the entertainment industry, and has 7 children with 4 different women.

Misa Hylton

Designer – stylist Misa Hylton was Diddy’s first public relationship, they were together when the rapper was just starting his music career. They have a son together named Justin (born in 1993). After “going their separate ways”, the two raised their child together. The rap mogul’s eldest son graduated from college in 2016 and has pursued a career in acting and hosting. In the middle of last year, Justin was arrested for drunk driving and sentenced to three years of probation.

Kim Porter

Diddy’s longest relationship was with model and actress Kim Porter. They dated since 1994, broke up and got back together before calling it quits in 2007. The couple welcomed son Christian “King” Combs in 1998 and twin daughters D’Lila Star and Jessie James Combs in 2006. Diddy also adopted Quincy (Kim’s child from a previous relationship).

Notably, 5 months before welcoming the twins with Kim, Diddy had a daughter named Chance with his partner Sarah Chapman. Kim later learned of the news through a friend and lost respect for her longtime partner.

Diddy had a child with Sarah Chapman while with Kim Porter

In 2018, Kim passed away at the age of 47. The rapper said: “We were more than best friends, we were more than soul mates. We were something very different… I miss you so much.” The star also called Kim’s passing a “nightmare” loss.

Recently, when Diddy was involved in a sex scandal that shocked the American public, Kim Porter’s death and their relationship caused a stir again. The incident caused even more stir when a document believed to be the late model’s memoir was circulated, mentioning the 55-year-old rapper’s debauched life and the artist’s abuse of Kim. Conspiracy theories about Kim’s passing also caused heated discussions. The incident caused the couple’s children to speak up to affirm that it was not what their late mother wrote and hoped to end the misinformation.

Jennifer Lopez

Diddy dated Jennifer Lopez in 1999 when the rapper’s relationship with Kim Porter was in trouble. The couple dated for about 2 years, constantly stunning with lavish parties, walking together at major events, and this relationship even got J.Lo into trouble because of her involvement in a shooting at a nightclub in New York.

They broke up in 2001 and the singer described them as having a crazy, chaotic relationship that ended in a big bang. The On the Floor singer shared that she ended everything because she felt she could never have the family life she wanted with the rapper. She also mentioned her past affair. After Diddy was arrested last week, old party photos of the couple were resurfaced and caused a stir.

Cassie Ventura

Diddy’s other relationship that is causing a stir is with singer, actress, and model Cassie Ventura. The 8X beauty started dating the owner of the hit I Need a Girl in 2007, they went through many ups and downs, sometimes breaking up, sometimes getting back together before ending it completely in 2018. After ending this relationship, Cassie married Alex Fine in 2019 and had two children.

In November 2023, Cassie Ventura caused a stir in public opinion when she filed a lawsuit against her ex-boyfriend, accusing the rapper of physical abuse, violence, controlling her for decades (including forcing her to have sex with prostitutes) and raping her when she was trying to escape Combs’ grip.

Diddy denied all accusations and settled with his ex-girlfriend, affirming that this action was in no way an admission of wrongdoing. In May 2024, a video of this infamous star beating Cassie Ventura in 2016 was suddenly leaked, forcing Combs to apologize for his violent actions.

Yung Miami

Diddy has been with rapper Yung Miami since 2021. The Gotta Move On singer once shared that they dated, went to exotic places, had a great time and are still good friends. “You’re like one of the most down-to-earth people I’ve ever met, you’re yourself, you’re a great mom, you’re a great friend and we just have a good time,” the male star told Miami.

By 2023, the 9X female rapper confirmed that she and Diddy were no longer dating. They were still good friends but the “rap kingpin” was not her man. “We had a very intense relationship. At one point, we were together every day. He supported me, I supported him. I’ll let the internet call it whatever they want,” she shared.

Gina Huynh

During his on-and-off relationship with Cassie Ventura, Diddy dated model Gina Huynh. In 2019, Gina revealed that the I’ll Be Missing You singer had abused her mentally, emotionally, and physically. The beauty also revealed that Diddy had offered her $5,000 for an abortion. “I refused money because I only loved him… I’m not the kind of girl who wants to be with him for money. I only care about him. I just want him to be nice to me,” she added.

In 2022, the beauty posted an intimate photo with Combs, hinting at a reconciliation with the scandalous star. Yung Miami then responded with a suggestive tweet: “Someone, please pay attention to this girl.”

Dana Tran

In December 2022, while still in a relationship with Yung Miami, Diddy welcomed his daughter Love but did not mention her mother. Later, TMZ revealed that the girl’s mother was Dana Tran (28 years old), who works in the cybersecurity industry. They have never mentioned their relationship and Us Weekly’s source also denied rumors that the two had secretly married. According to what this beauty shared on social media, she is of Vietnamese origin and has a beautiful, hot appearance.

Diddy’s sudden announcement of having a child with someone else forced Yung Miami to clarify that she was not a “mistress”. The 9X rapper also shared that she was not surprised when the child was born. While Combs was being detained with a series of serious charges, Dana Tran still enjoyed her private life, sharing many happy photos with her daughter, not posting any content about her child’s father.

In addition to the above names, Diddy is also rumored to be dating Naomi Campbell, Cameron Diaz, Lori Harvey… and has been accused of sexual misconduct by many women.