Sean 'Diddy' Combs’ romantic past, from Jennifer Lopez to tragic death of Kim Porter

The life of Sean "Diddy" Combs is under intense scrutiny, including his past and present relationships.

On Monday, two of Combs' homes in Los Angeles and Miami were raided as part of a federal human trafficking investigation. 

Combs declared his innocence, and his attorney, Aaron Dyer, told Fox News Digital in a statement Tuesday, "There has been no finding of criminal or civil liability with any of these allegations. Mr. Combs is innocent and will continue to fight every single day to clear his name."

Additionally, Rodney Jones, known professionally as Lil Rod, sued Combs in February for sexual assault and listed the rapper’s most recent girlfriend, Yung Miami, in his updated complaint on Monday, alleging she was paid as a sex worker by Combs and also provided him with drugs.

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Combs has also faced prior legal issues with his dating life, including a lawsuit by ex-girlfriend Cassie alleging years of abuse. 

Read on for more details about the rapper’s complicated and high-profile dating history.

Misa Hylton

Misa Hylton is a fashion designer who began dating Combs in the early 1990s.

They welcomed a son together, Justin, in 1993 and have co-parented him since their breakup shortly after.

In 2023, Hylton appeared to call out Combs on social media when Justin was charged with a DUI, writing, "I’m not protecting no one anymore, just my son."

She also implied Combs had been "sit[ting] around for years and act[ing] like there isn’t anything wrong with you."

"The statement ‘a fish rots from the head down’ means that, in addition to being a major contributing [factor] in a family or organization’s success, leadership is also the root cause of its failure and demise," she added.

They later exchanged more positive interactions at the time on Instagram after Diddy posted that he felt like it was "f--- everybody" season, and she agreed in a comment. He wrote in response, "I love you queen. Stay in the light."

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Kim Porter

Model Kim Porter and Combs dated on and off from the 1990s through 2007, when they broke up following his alleged infidelity.

"He’s not the first man who’s cheated," Porter told Essence magazine in 2007. "He’s not the first man who’s had a baby outside of his relationship. He’s not the originator of this. But at this point in my life — I have girls now — it’s a different program."

Combs adopted Porter’s son Quincy from a previous relationship, and they shared three more children together, son Christian and twin daughters D’Lila and Jessie.

Despite the alleged infidelity, they remained friendly throughout the years until her sudden death from lobar pneumonia in 2018 at age 47.

Combs paid tribute to Porter on social media, writing, "We were more than best friends, we were more than soulmates. WE WERE SOME OTHER S---!!"

Calling it a "nightmare" loss, he added, "I miss you so much." 

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Jennifer Lopez

Combs dated Jennifer Lopez from 1999 to 2001 during one of his breaks from Porter but called it quits due to his alleged infidelity.

In 2003, Lopez spoke about the breakup in Vibe, telling the outlet, "It was the first time I was with someone who wasn’t faithful.

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"I was in this relationship with Puff [Combs] where I was totally crying, crazy and going nuts. It really took my whole life in a tailspin."

There were reports during the relationship that Lopez would try to hunt him down and even knocked on hotel doors looking for him, to which she responded, "I can’t remember right now, but I won’t say it didn’t happen.

"I never caught him, but I just knew. He’d say he was going to a club for a couple of hours and then never come back that night," she added.

During their relationship, Combs, Lopez and rapper Shyne were at a New York City nightclub when gunfire broke out and injured three people, including a woman who was shot in the face.

Lopez and Combs fled and were pulled over, and a gun was found in their vehicle. Lopez was released, but Combs and Shyne were charged with multiple offenses. Combs was later found not guilty at trial.

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Sarah Chapman

Though they never formally dated, Combs and Sarah Chapman welcomed a son, Chance, in 2006, while his ex, Porter, was expecting their twins.

Porter expressed her disappointment in a 2007 Essence interview, saying, "But men do get caught up in things; I’m not naive to that. Still, there’s a right and a wrong way to handle it.

"Because, most of all, we were friends. Even if I couldn’t have understood it as a woman, I would have understood it as a friend."

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According to Porter, Combs confessed after their twins were born, and she said she already knew of his affair with Chapman.

"I said, ‘Really? Well, I already knew. I’m glad you decided to be a man,’" Porter told the outlet. "I was like, ‘Dude, this is so wack. I can’t even respect you right now.’ And, for me, once the respect is gone, I’m not even listening to you."

Chapman and Combs have remained friendly over the years, with the mogul recently wishing her a happy birthday on social media last year.

Cassie

Combs began a relationship with Cassie, whose full name Cassandra Ventura, a singer signed to his Bad Boy Records label in 2007.

Engagement rumors surfaced in 2014, followed by breakup rumors the next year and a reconciliation in 2016.

They called it quits for good in 2018, with Cassie’s rep stating they had been apart "for months," according to the New York Post.

In 2023, Cassie filed a lawsuit against Combs, claiming he had abused and raped her during their relationship, which they began two years after they first met, when she was 19 and he was 37.

The suit claimed Combs had "uncontrollable rage" and alleged he beat her on multiple occasions.

"After years in silence and darkness, I am finally ready to tell my story, and to speak up on behalf of myself and for the benefit of other women who face violence and abuse in their relationships," Cassie, 37, told Fox News Digital in a statement. 

Combs denied the claims and ended up settling the suit one day after it was filed.

"I have decided to resolve this matter amicably on terms that I have some level of control," Cassie said at the time. "I want to thank my family, fans and lawyers for their unwavering support." 

Combs said in his own statement, "We have decided to resolve this matter amicably. I wish Cassie and her family all the best. Love."

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Yung Miami

Rapper Yung Miami and Combs confirmed their relationship in 2022 when he appeared on her podcast, "Caresha Please," part of Combs’ REVOLT podcast network.

She later made a confusing statement about their relationship in XXL Magazine, saying, "We are dating. We single, but we’re dating. People don’t know what dating means. He’s single, I’m single, but we’re dating. That’s what I mean when I say we go together. When we’re together, we’re together. We’re having the time of our lives, but we’re still single."

The pair attended the 2023 Met Gala together last year.

Yung Miami, whose legal name Caresha Romeka Brownlee, is named in a complaint by Rodney Jones against Combs, alleging she was one of several women "paid a monthly fee to work as Mr. Combs’ sex workers."

The filing also alleges she transported drugs on behalf of Combs, describing his preference for "tuci" a "pink drug that is a combination of ecstasy and cocaine."

"Plaintiff and the Combs Rico Enterprise were rehearsing for ‘something in the water festival’ in Virginia. Plaintiff Jones personally witness Mr. Combs do a few lines of coke in his dressing room. Defendant Sean Combs wanted tuci, but Brendan forgot it, so Defendant Kristina Khorram called Yung Miami, who then brought it on the private jet from Miami," the lawsuit alleged.

Representatives for Yung Miami did not immediately return Fox News Digital’s request for comment.

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Dana Tran

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Combs and Dana Tran welcomed a daughter, Love, in 2022, his seventh child. 

The exact nature of their relationship is unclear, though they run a joint Instagram account for their daughter.

On her "Caresha, Please" podcast at the time of Love’s birth, Yung Miami stated she was aware of the infant’s existence.

"I think communication is key … when you’re dealing with somebody. It wasn’t, like, a surprise," she said, per the New York Post.

Diddy also took to X, formerly Twitter, to state that the rapper "is not my side chick. Never has been, never will be.

"She’s very important and special to me, and I don’t play about my Shawty Wop. I don’t discuss things on the internet and I will not start today." 

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Gina Huynh

Gina Huynh was linked to Combs during his on-again, off-again relationship with Cassie.

In 2019, she alleged to blogger Tasha K that Combs had abused her, saying, "He stomped on my stomach really hard — like, took the wind out of my breath," per the New York Post.

"He was mentally, emotionally and physically abusing me. He would always compare me to Cassie and tell me that I’m the bad one, she’s a good one."

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The interview resurfaced in 2023 after Cassie’s lawsuit against Combs. 

Huynh claimed she turned down $50,000 to get an abortion after becoming pregnant by Combs.

"I turned [the money] down because I just loved him. I wanted to … I was, like, trying to prove that," she claimed, according to the Daily Mail.

"I wasn’t the girl that wanted him for money. I just cared about him. I just wanted him to be nice to me. That’s it."

Fox News Digital's Caroline Thayer contributed to this report.