His Dating History From J.Lo To Cassie Ventura – Hollywood Life

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“See, Diddy is my nickname. Love is my real name. I just changed my name to Love,” the man born Sean Combs said during his final appearance on The Ellen DeGeneres Show in May 2022. “Sean Love Combs, that’s what it says on my driver’s license, that’s my official name, Love.” Although the rapper was recently arrested in New York on Monday, September 16, and charged with racketeering, sex trafficking, and transporting individuals for prostitution, the hip-hop icon and spirits connoisseur has had a life filled with romance and sensuality, involving a long list of women over the years. Though Kim Porter will always have a special place in Diddy’s soul, he was romantically liked to other famous women like Jennifer Lopez, Lori Harvey, Yung Miami, and more.

But apparently, his dating history hasn’t been without drama. In November of 2023, Cassie accused the rapper of a string of alleged offenses, including claims of rape and other abuses. Although the case was reportedly settled, Diddy has been accused of sexual assault by multiple women and was taken into custody by federal agents in September 2024, following raids on his homes in March earlier that year. Here’s what to know about each of his most notable romantic relationships.

Kim Porter

Sean Combs began dating Kim Porter in 1994. “The first time I saw her, she was at the studio with her ex-boyfriend,” Diddy told Essence, referring to singer Al B. Sure, the father of Kim’s oldest child, Quincy. “I wasn’t trying to holler at her or anything, but I was admiring her—her lips, her eyes, her mouth, her shape, her energy—and thinking, ‘I wish I had a girl like that.’”

 She kind of made me nervous,” he told Essence. “She wasn’t like a New York girl. She was Bohemian, mixed with Georgia-peach hospitality. I got the idea she’d like doing stuff like walking barefoot in the grass. I didn’t think I could get her to like me. She was smooth, you know, like ice. She’s cool and collected and thinks before she speaks. You meet a lot of young ladies, and they just don’t do that. Kim was never pressed; she was always in control.”

While Kim was in control, Diddy wasn’t always in control of his love. Kim and Diddy split in 1999, as he began seeing Jennifer Lopez. The two rekindled their love in 2003, before splitting for good in 2007.

During their time together, Diddy and Kim started a family. They welcomed Christian “King” Combs in 1998 and twin daughters D’Lila Star and Jessie James Combs in 2006. Diddy would also help raise Quincy, eventually adopting the boy as his son.

Tragically, Kim passed away in 2018 at the age of 46. She died in her sleep from lobar pneumonia.

Misa Hylton Brim

Misa Hylton Brim is a designer and stylist credited with putting together some incredible looks from the 1990s, per Capital XTRA. She is also known as Diddy’s high school sweetheart and the mother of his son, Justin Combs. Misa and Diddy welcomed Justin in 1993. Since then, they have co-parented their son together.

“Kim, for the last 20 years we have raised our children together, my mind cannot begin to wrap around the fact that you are not going to be here,” Misa wrote following Porter’s death, per PEOPLE. “Thank you for being a 2nd mother to Justin and for loving Niko and Madison just the same,” she added, referring to her children from another relationship.

Sarah Chapman

Diddy had a brief romance with Sarah Chapman in the early 2000s. It was long enough for them to welcome a daughter, Chance Combs, who was born shortly before twins D’Lila and Jessie. The romance didn’t last much longer after Chance’s birth, though Sarah didn’t seem to hold any ill will. When Kim Porter passed away, she too mourned the loss.

“Rest in paradise Kim, and know your kids are covered in prayer and love,” she wrote on Instagram, per PEOPLE. “Your light will always shine thru your children and the way they all love each other is a blessing beyond words.”

Jennifer Lopez

One of the highest-profile romances of the late ’90s/early 2000s was that of Sean Combs and Jennifer Lopez. In 1999, Sean began dating J.Lo (while he was still with Kim, which triggered the split.) J.Lo and Diddy stayed together for two years,

“The Puffy era was just kind of a crazy, heightened time in my life. You know, Puffy and I both grew up in the Bronx,” J.Lo told The Breakfast Club in 2019. “He had been in the music business and had all this success; I was just starting and making my first album when I met him. He became kind of a mentor to me in that moment. We had this kind of crazy, tumultuous relationship that ended in a bang.”

“It was definitely a moment but I felt like it was necessary,” she added. “He was meant to be in my life at that moment to teach me what I needed to know about the music business, about what kind of artist I wanted to be in the music industry.”

The couple announced their split on Valentine’s Day 2001. “Mr. Combs confirmed that he and his love, Jennifer Lopez, have, in fact, broken up,” his publicist said at the time, per Newsweek. “Mr. Combs is confirming this today, as he wanted to put all the rumors surrounding their relationship to rest. At this difficult time, we ask that you respect his privacy.”

J.Lo would later say in an interview that she ended things because she’d never have the family life she wanted with the rapper. Plus, who can forget the drama of the Dec. 1999 nightclub shooting that saw Diddy and J.Lo arrested, before they were ultimately cleared of all charges.

Naomi Campbell

For a hot second, Diddy was romantically linked to one of the most beautiful women in the world. Dating rumors swirled around Diddy and Naomi Campbell in 2001, when the two were photographed together in British Vogue in 2001. It’s thought that things went romantic in 2002, but the couple never confirmed a relationship. Things remained platonic after the end of their rumored romance.

Cassie

Cassie (aka Cassie Ventura) began dating the Bad Boy Icon in 2007. The on-and-off romance was mostly secret until 2012. The couple went public with their love, which continued until they split in 2018. Diddy was reportedly not interested in putting a ring on Cassie’s finger, so she left him. Four years after that breakup, Diddy released a song about how he had to “move on” and stop mourning the loss. However, in 2022, he thanked Cassie “for holding me down in the dark times” when accepting the Lifetime Achievement Award at the BET Awards.

Since splitting from Puff, Cassie married Alex Fine in 2019, and the couple welcomed two children together. But in November of 2023, she filed a lawsuit in New York City, alleging a number of complaints, including rape and abuse during their relationship, against the rapper. In papers filed in Federal District Court in NYC and reported on by the New York Times, she leveled accusations of “rape, and of repeated physical abuse over about a decade.”

“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 obtained by the NYT.

Combs hit back hard through a statement by his lawyer, Ben Brafman. “Mr. Combs vehemently denies these offensive and outrageous allegations,” Combs’ rep said in a statement. “For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail. 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’s reputation and seeking a payday.”

Cameron Diaz

Considered more of a short-term fling between two ’90s icons, Diddy and Cameron Diaz had a brief romance in 2008. In 2014, Us Weekly reported that Diddy was at a dinner where the subject of Cameron dating Benji Madden came up and said “If I could turn back time, things would be different.”

Lori Harvey

One of Diddy’s most recent love affairs was with Steve Harvey’s daughter, Lori Harvey. The two sparked talk of a romance in July 2019, after they were spotted spending time together. Diddy even joined Lori on vacation in Italy with the Family Feud host and Steve’s wife, Marjorie Elaine Harvey. However, the relationship (that neither publicly confirmed) didn’t last that long. Lori stopped following Diddy online in October 2019 after he was spotted out with another woman.

Gina Huynh

Gina Huynh, a Los Angeles-based model, was once linked to Diddy in 2019. In 2022, following the Billboard Awards, Gina claimed that she and Diddy were giving love a second shot by posting a picture of him kissing her cheek on her Instagram Story. This caught the attention of Puff’s girlfriend at the time, Yung Miami, who called out for “somebody, please give this girl some attention.”

Yung Miami

“I’m single. But I’m dating, I’m just taking my time with life,” Diddy said on the June 9, 2022, episode of Caresha Please, the podcast hosted by his then-girlfriend Yung Miami. Even though Diddy said he was single, he acknowledged that he and Miami (b. Caresha Brownlee) were an item. “We’re dating. We go have dates. We’re friends,” he said. “We go to exotic locations. We have great times.”

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

However, the 29-year-old rapper confirmed in an April 2023 interview with The Cut that she’s no longer dating the Bad Boy Records mogul.  “We’re still friends! We’re still good friends!” she said. “But we’re single. That’s not my man.” She further explained that the relationship had been intensely intimate.

“We were f*cking with each other hard. We were together every day at one point,” she said. “He supported me, I supported him. I’ll let the internet call it whatever they want to call it.”