Jennifer Lopez Dating History: What to Know About the singer’s Relationships

The intimate details of Sean “Diddy” Combs’ personal life are being discussed at his ongoing federal criminal trial.

In September 2024, Combs was arrested and charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He pled not guilty and was denied bail multiple times ahead of his trial in New York City, which began on May 12.

The accusations against Combs first came to light when his ex-girlfriend Casandra “Cassie” Ventura filed a lawsuit against the rapper in November 2023, alleging that Combs raped and sexually trafficked her over the course of their decade-long relationship. The exes reached a settlement one day later.

In the following months, numerous other lawsuits were filed against Combs, 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.

Two months later, a video was released showing Combs allegedly abusing Cassie in a hotel in March 2016. Combs later confirmed it was him in the video and apologized for his actions.

On May 13, Cassie was called to the witness stand at Combs’ trial. In her testimony, she claimed that the rap mogul “controlled” her life when they were together and forced her to participate in sexual encounters.

Prior to his relationship with the “Me & U” singer, Combs dated Jennifer Lopez from 1999 to 2001. He went on to welcome four children with the late Kim Porter, whom he started dating in the ’90s before their final split in 2007.

Combs also shares a son, Justin, with fashion designer Misa Hylton and a daughter, Chance, with his friend Sarah Chapman. In 2022, Combs announced the birth of his seventh child, Love, with Dana Tran.

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

Misa Hylton

Combs 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 the 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.”

Combs 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 Combs’ 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 Stories, 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 Combs’ lawsuit against the alcohol company, Diageo, which he sued for racial discrimination, alleging they failed to promote the Ciroc and DeLeon brands. Combs 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 couple appeared to make up shortly after when Hylton commented on Combs’ Instagram post and he replied, “I love you queen. Stay in the light.”

Kim Porter

Combs and Porter started dating in the 1990s and welcomed their first child together, Christian, on April 1, 1998. Combs 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 Combs was expecting a child with his friend Sarah Chapman in 2006 — while she was pregnant with their twins, D’Lila Star and Jessie James — she felt that he betrayed her, she later told Essence.

Porter told the outlet that she found out through a friend and regretted that Combs 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 their twins were born in December 2006, Combs 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 Combs 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 Combs praising Porter as an “incredible mother” in an interview with JET magazine.

After she died, Combs 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

Combs 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, Combs posted a throwback picture of the two.

Sarah Chapman

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

Despite the rocky start to the parenting journey, Combs 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, Combs 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, Combs entered into a relationship with singer Cassie, whose real name is Casandra 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 Combs of raping and abusing her over the course of their relationship. The complaint, which was obtained by PEOPLE, said that Cassie first met Combs 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 Combs 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 Combs forced his way into her home and raped her.