A Look at Diddy's Past Girlfriends, From Jennifer Lopez to Cassie

Diddy has had a number of relationships with famous stars including Jennifer Lopez and Cassie

Diddy, né Sean Combs, has had numerous relationships in the public eye since his rise to fame in the 1990s.

The “I’ll Be Missing You” rapper has been linked to famous stars from Jennifer Lopez to Cassie throughout his career. His longest relationship was with Kim Porter, whom he started dating in the 1990s before their final split in 2007.

Diddy and Porter, who died in 2018, raised four children together. Diddy also welcomed a son, Justin, with fashion designer Misa Hylton and a daughter, Chance, with his friend Sarah Chapman. In 2022, Diddy announced the birth of his seventh child, Love, with Dana Tran.

In November 2023, Cassie filed a lawsuit against Diddy alleging he raped and sexually trafficked her over the course of their decade-long relationship. In the complaint, Cassie claimed she was stuck in a “cycle of abuse, violence and sex trafficking” for 10 years, and when she tried to end the relationship for good in 2018, he allegedly raped her.

“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,” she said in a statement. “With the expiration of New York’s Adult Survivors Act fast approaching, it became clear that this was an opportunity to speak up about the trauma I have experienced and that I will be recovering from for the rest of my life.”

Diddy’s lawyer Ben Brafman denied the allegations in a statement to PEOPLE, calling them “offensive and outrageous.”

The following day, Diddy and Cassie announced they settled and resolved the claims in the lawsuit to their "mutual satisfaction."

“I have decided to resolve this matter amicably on terms that I have some level of control,” Cassie said in a statement. “I want to thank my family, fans and lawyers for their unwavering support.”

Related: A Timeline of Sean 'Diddy' Combs' Sexual Assault Allegations and Lawsuits

In the following months, numerous other lawsuits were filed against Diddy accusing him of sexual assault, which he has denied. In March 2024, the rapper's properties in Los Angeles, Miami and New York were raided amid allegations of sex trafficking.

"Earlier today, Homeland Security Investigations (HSI) New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners. We will provide further information as it becomes available," a Homeland Security Investigations representative said in a statement to PEOPLE.

From Jennifer Lopez to Cassie, here’s a complete look back at Diddy’s dating history.

Misa Hylton

Diddy started dating fashion designer Misa Hylton in the early 1990s when he was just coming up in the music industry. He helped Hylton get her big break when he hired her to style music group Jodeci.

“We were dating at the time and he had just went from intern to A&R,” she told BET in March 2023. “He had a new position at Uptown Records and he was in charge of putting together the album musically but also for their look.”

Diddy and Hylton welcomed their only child, Justin, on Dec. 30, 1993. While the pair seemed to break up shortly after, they remained close as they raised Justin, with Hylton even attending Diddy’s 50th birthday party in 2019.

In June 2023, she seemed to air her grievances with her ex on her Instagram after Justin was arrested and charged with a misdemeanor for a DUI. On her Instagram Story, Hylton wrote "this [is] where the buck stops" for her after "sit[ting] around for years and act[ing] like there isn't anything wrong with you."

She seemingly referred to Diddy’s lawsuit against the alcohol company, Diageo, which he sued for racial discrimination, alleging they failed to promote the Ciroc and DeLeon brands. Diddy signed with Diageo to become the face of Ciroc in 2007, though their marketing agreement has since been terminated. They teamed up again in 2013 to launch the tequila brand DeLeon.

"How [do] you go from one of the greatest to ever do it to making all your money off alcohol and suing the damn alcohol company," Hylton wrote. "Sell something healthy that builds people up. I’m sick of it!!!!! NOT MINES."

The pair appeared to make up shortly after when Hylton commented on Diddy’s Instagram post and he replied, “I love you queen. Stay in the light."

Kim Porter

Porter and Diddy started dating in the 1990s and welcomed their first child together, Christian, on April 1, 1998. Diddy also considers Porter’s first son from a previous partner, Quincy, as his own.

Though they broke up a year after Christian’s birth and battled in court over custody, they stayed close and were on and off for a long while after.

When Porter found out that Diddy was expecting a child with his friend Sarah Chapman in 2006 — while she was pregnant with the pair’s twins, D’Lila Star and Jessie James who were born in December that year — she felt that he betrayed her, she later told Essence.

She told the outlet that she found out through a friend and regretted that Diddy hadn’t told her himself.

“I would have preferred to find out from him because that’s a man,” she said. “I know it’s hard for anyone to say to their significant other, ‘I’ve gotten into some s— and I got a baby on the way.’ 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.”

After her twins were born, Diddy owned up to the truth and Porter revealed that she already knew.

“I said, ‘Really? Well, I already knew. I’m glad you decided to be a man,’ ” she recalled. “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.”

In July 2007, Porter called it quits with Diddy for the last time. "In ending this relationship, I made a decision that was in the best interest of myself, Sean and our family. I look forward to moving on with my life and my career and wish him prosperity, health and happiness in life and in love. We will remain friends and committed parents to our children," Porter said in a statement at the time.

However, the two remained close friends until her death in 2018 from lobar pneumonia and frequently spoke positively about each other, with Diddy praising Porter as an “incredible mother” in an interview with JET magazine.

After she died, Diddy has continued to post about Porter, including on the anniversary of her death and on what would have been her 50th birthday in 2020.

Jennifer Lopez

Diddy started a relationship with Lopez in 1999 and the two dated for two years before splitting in 2001, with the “On the Floor” singer citing his infidelity as the cause in a 2003 interview with Vibe.

They attended the 2000 Grammy Awards where Lopez donned her famous green Versace dress.

“I thought it was gonna really change the game as far as for her and fashion,” he told Entertainment Tonight in 2017. “I didn’t know how big it was gonna be, but it was a great moment for her.”

He added that Lopez was “without a doubt” one of his greatest loves. The former pair remained friendly since their split — they reunited at a party in 2018 and, in 2021, Diddy posted a throwback picture of the two.

Sarah Chapman

While Diddy and Chapman, who is a businesswoman, never dated, they were friends for years and welcomed a child, Chance, together while Diddy was still in a relationship with Porter.

Despite the rocky start to the parenting journey, Diddy has remained close to Chapman as they raised Chance together and he still regularly posts with gratitude for the mother to his eldest daughter.

For her birthday in September 2023, Diddy posted a tribute on Instagram, writing, “Thank God for you everyday! We are so grateful to have you in our lives! Love you.”

Cassie

Following his final break with Porter, Diddy entered into a relationship with singer Cassie, whose real name is Cassandra Ventura, in 2007. They were on-again-off-again for nearly a decade, calling it quits for the last time in 2018.

In November 2023, Cassie accused Diddy of raping and abusing her over the course of their relationship. The complaint, which was obtained by PEOPLE, said that Cassie first met Diddy when she was 19 and he was 37, and he had just signed her to his label Bad Boy Records.

She alleged that before long he had “complete control” over her life and when he pursued a relationship with her, she agreed because she feared retaliation if she denied him, per the complaint.

“All aspects of Ms. Ventura’s life were controlled by either Mr. Combs or his management companies,” the complaint said.

The complaint also alleged that Diddy could be physically abusive to her, once stomping on her face and forcing her to hide in a hotel room for a week until her bruises healed.

“She found herself becoming numb to the abuse she was experiencing, and became entirely beholden to Mr. Combs’s demands,” the complaint read. “She began to blindly follow his instructions out of fear of again being on the receiving end of a vicious beating.”

Once Cassie decided to fully end the relationship in September 2018 over dinner, she alleged Diddy forced his way into her home and raped her.

In a statement to PEOPLE, Diddy's lawyer Brafman said, "Mr. Combs vehemently denies these offensive and outrageous allegations. Ms. Ventura's demand of $30 million, under the threat of writing a damaging book about their relationship, was unequivocally rejected as blatant blackmail."

The statement continued, "Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs' reputation, and seeking a pay day."

However, the day after she filed the lawsuit, Diddy and Cassie settled and shared that no further details about the terms of their agreement would be released publicly.

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

Brafman clarified Diddy's stance on the issue in a statement to PEOPLE, saying, "Just so we’re clear, a decision to settle a lawsuit, especially in 2023, is in no way an admission of wrongdoing. Mr. Combs‘ decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims. He is happy they got to a mutual settlement and wishes Ms. Ventura the best."

Following their breakup, Cassie married personal trainer Alex Fine in 2019 and has welcomed two children with him.

Lori Harvey

In July 2019, Diddy and Lori Harvey were rumored to be dating as they were seen taking a stroll through New York City’s SoHo neighborhood together. A month later, they were seen vacationing with Harvey’s parents, Marjorie and Steve Harvey, in Italy.

However, just a few months later, in October, it appeared the two had split as Harvey unfollowed Diddy on social media days after he was spotted grabbing dinner with another woman.

In January 2023, Harvey denied the rumors that she had dated both Diddy and his son Justin. When asked by E! News host Adrienne Bailon what the “biggest misconception” about her was, Harvey replied, “I've heard I dated a father and son before. Absolutely not true.”

Yung Miami

Diddy and City Girls rapper Yung Miami were first linked in 2021 but only confirmed their relationship in June 2022 when Diddy appeared on her podcast.

"We date," he responded after Yung Miami asked him, "So what we is?"

"We're dating. We go have dates. We're friends. We go to exotic locations. We have great times," Diddy stated.

Related: Diddy and Yung Miami's Relationship Timeline

A few months later, in September 2022, Yung Miami clarified in an interview with XXL Mag that she was “single” but they were dating.

"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," she said.

The two later attended the 2023 Met Gala together, where Diddy explained to host La La Anthony that they “don’t put titles” on their relationship. The previous month, Yung Miami told The Cut that she was single and Diddy was “not [her] man.”

Dana Tran

Though Diddy hasn’t ever confirmed a relationship with Dana Tran, who is a cybersecurity professional, industrial specialist and model, the two did welcome a baby, Love, together in October 2022.

"I'm so blessed to welcome my baby girl Love Sean Combs to the world," he wrote on X. "Mama Combs, Quincy, Justin, Christian, Chance, D'Lila, Jessie and myself all love you so much! God is the Greatest!"

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