Diddy's Dating History: 12 Women the Rapper Dated and Was Linked To Through the Years

Diddy started his dating spree after meeting fashion designer Misa Hylton in the early 1990s. They welcomed their first and only child, Justin, on December 30, 1993, before their split afterward.

The pair had several heated exchanges over the past few years but patched things up already.

In 1994, Diddy found love again when he struck up a romance with Kim Porter following her relationship with Al B. Sure. They continued to have an on-again, off-again relationship for years until their first child, Christian, arrived on April 1, 1998.

While pregnant with their twins — D'Lila Star and Jessie James — in 2006, she discovered that the I'll Be Missing You rapper was also expecting his child with her friend Sarah Chapman. She told Essence that she felt he betrayed her and regretted how she learned about it.

"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."

Porter continued, "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."

They broke up for good in July 2007 and remained friends until she died in 2018.

Jennifer Lopez was also part of Diddy's dating list, and she shared a two-year relationship with him starting in 1999 following his and Porter's initial split. They broke up in 2001 due to his infidelity, but they remained friendly after what happened.

The It's All About the Benjamins hitmaker dated Joie Chavis, Chapman's close friend, following his failed relationships. RadarOnline.com learned that the fitness entrepreneur and Diddy followed each other online and interacted by liking each other's posts.

The buzz about their relationship eventually died down.

Diddy and Naomi Campbell ignited a dating buzz when they worked together in a British Vogue photoshoot in 2001. Reports said things went romantic in 2002, but they never commented on the news until they were linked to other people.

Diddy had an on-and-off romance with Cassie Ventura starting in 2007 until 2018. They met when she was 19 when he signed her to Bad Boy Records.

She dropped a bombshell last week when she accused the record executive of raping and abusing her during their 10-year relationship. Diddy's lawyer issued a statement debunking the "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 representative said. "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."

They settled a day after her lawsuit filing. The terms of the agreement remain unknown as of press time.

Diddy and Cameron Diaz shared a short-lived romance in 2008. Years after their breakup, the former Uptown Records director reportedly said during a dinner that things would be different between them if he "could turn back time."

Steve Harvey's daughter Lori Harvey sparked dating rumors with Diddy when they went to Italy for a family vacation. After the buzz surfaced, she unfollowed him on his social media accounts.

Gina Huynh was linked to Diddy in 2019, years before renewing the buzz after kissing him on the cheek following the Billboard Awards 2022. However, at that time, Diddy was dating Yung Miami, who wrote, "Somebody, please give this girl some attention!" after seeing the photo.

During the June 9, 2022, episode of Miami's "Caresha Please" podcast, Diddy said he was single "but dating" the host.

"You're like one of the realest people I've ever met and you're authentically yourself," he told her. "You're a great mother and a great friend. We just have a good time."

Yung Miami confirmed in April that they were no longer dating.

Diddy welcomed his baby, Love, with model Dana Tran in October 2022. They never confirmed their relationship, and the buzz disappeared months after being linked.