Sean ‘Diddy’ Combs’ relationship history: The embattled music mogul’s girlfriends, exes

Early in his career, the Bad Boys Records founder began dating fashion designer Misa Hylton.

The pair welcomed their first child, a son named Justin, in December 1993 and have co-parented him since their split.

Hylton made headlines for shading her ex in June 2023 after Justin’s DUI arrest, writing via Instagram that Diddy had been “sit[ting] around for years and act[ing] like there isn’t anything wrong with you.”

Kim Porter

Diddy dated model Kim Porter on and off from the 1990s through 2007, with the former couple remaining friends after breaking up for good.

While they were together, the songwriter adopted his partner’s son Quincy from a previous relationship.

The duo went on to welcome three more children of their own: son Christian and twin daughters D’Lila and Jessie.

When they called it quits, Porter wrote in a statement she wished Diddy “prosperity, health and happiness in life and in love.”

Porter died in November 2018 at age 47.

“We were more than best friends, we were more than soulmates. WE WERE SOME OTHER S–T!!” Diddy wrote via Instagram in the wake of the “nightmare” loss. “I miss you so much.”

Jennifer Lopez

Jennifer Lopez dated the “Coming Home” rapper for two years, with the exes confirming their split on Valentine’s Day in 2001.

Diddy gushed over the “Let’s Get Loud” singer in 2017, telling “Entertainment Tonight” that “she is one of the flyest out there.”

When Lopez rekindled her relationship with Ben Affleck in 2021, Diddy seemingly taunted them by posting a throwback PDA pic via Instagram — only to later insist he wasn’t “trolling” the couple.

Naomi Campbell

Diddy was rumored to be dating Naomi Campbell in 2002, but the duo never confirmed the romance.

They do, however, remain friends, with the record executive attending the supermodel’s 54th birthday party in November 2023.

After Cassie sued Diddy that same month, Campbell deleted photos of him from her Instagram.

Sarah Chapman

Although Diddy and Sarah Chapman never officially dated, the friends welcomed son Chance in 2006 while he was expecting twins with Porter.

Porter found out through a friend and lost “respect” for the Grammy winner.

“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,” she told Essence of the “wack” scenario (via People). “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.”

Cassie

Cassie and Diddy’s tumultuous relationship began in 2007, two years after he met the then-teenager while producing her first album.

While the pair primarily kept their relationship out of the spotlight, they made many red carpet appearances together and sparked engagement rumors in 2014.

The following year, Cassie hinted at infidelity via Instagram as breakup rumors swirled — only for them to reconcile by 2016.

By the time their split made headlines in October 2018, Cassie’s rep clarified that they had been apart “for months.”

When Cassie, who has moved on with husband Alex Fine, sued Combs in 2023, the lawsuit claimed that she “again and again tried to escape his tight hold over her life” before they called it quits for good.

In a statement, she wrote that she will be “recovering for the rest of [her] life” from the “trauma” and “years in silence and darkness” she allegedly experienced.

Cameron Diaz

Diddy and Cameron Diaz were believed to have engaged in a short-lived romance in 2008.

Us Weekly reported in 2014 that the “Hello Good Morning” rapper missed his former fling after she married Benji Madden.

He said over dinner that “things would be different … if [he] could turn back time,” according to the magazine.

Lori Harvey

One month after Diddy and Steve Harvey’s daughter Lori Harvey sparked dating rumors in July 2019, the duo were photographed vacationing in Italy with her parents.

Lori unfollowed Diddy on Instagram in October of that same year.

While the exes have yet to speak on their time together, Lori did deny rumors that she “dated a father and son before” amid speculation she also connected with Diddy and Hylton’s son, Justin.

Yung Miami

After months making headlines, Diddy appeared on Yung Miami’s “Caresha Please” podcast to clarify the status of their relationship.

“We’re dating. … We’re friends,” the BET Award winner said in the June 2022 episode.

The City Girls rapper, who continued to refer to herself as “single,” made her red carpet debut with Diddy at the 2023 Met Gala.

She has yet to comment on his ongoing legal battles.

Gina Huynh

Gina Huynh was linked to Diddy during his on-again, off-again romance with Cassie, alleging to blogger Tasha K in 2019 that he had stomped on her stomach and punched her in the head during a disagreement.

“He was mentally, emotionally and physically abusing me,” the model claimed at the time.

When Huynh posted a PDA pic with Combs in 2022 and hinted at a reconciliation, Yung Miami reacted with a shady tweet reading, “somebody, please give this girl some attention.”

Dana Tran

Diddy welcomed a baby girl named Love with Dana Tran in December 2022, leading Yung Miami to clarify she was not a “side bitch.”

She told podcast listeners that she wasn’t surprised by the infant’s arrival, explaining, “Communication is key … when you’re dealing with somebody.”

Similarly, Diddy insisted Yung Miami was not his “side chick” and was, instead, “very important and special to” him.