Diddy’s girlfriends all have one thing in common: they are beautiful and hot.

Diddy , whose real name is Sean Combs, has had several public relationships since he rose to fame in the 1990s.

The “I’ll Be Missing You” rapper has had a number of high-profile relationships involving celebrities ranging from Jennifer Lopez to Cassie throughout his career. His longest relationship was with Kim Porter, whom he began dating in the ’90s before their final split in 2007.

Diddy’s most high-profile relationship was probably his affair with Cassie. On November 17, 2023, Cassie filed a lawsuit against Diddy, accusing him of rape and sex trafficking during their ten-year relationship.

Misa Hylton

Diddy began dating fashion designer Misa Hylton in the early 1990s when he was just starting to make his name in the music industry. He helped Hylton get his big break when he hired her as a stylist for the band Jodeci.

Diddy and Hylton welcomed their only child, Justin, on December 30, 1993. The two split shortly after but remained in a relationship to co-parent Justin. Hylton even attended Diddy’s 50th birthday party in 2019.

In June 2023, Hylton expressed her frustration with Diddy when her son was arrested for drunk driving. It seems that according to Hylton, Diddy himself raised Justin poorly.

However, it seems the two have since made up after Diddy left a comment on Hylton’s Instagram.

Kim Porter

Of Diddy’s girlfriends, he and Porter probably had the longest, albeit on-and-off, relationship. Porter and Diddy officially dated in the 90s. In 1998, Porter and Diddy welcomed their son Christian. Diddy also considered Quincy – Porter’s first son with his lover – as his own. 1 year after Christian was born, the two officially broke up and even took each other to court over a custody dispute. However, the two quickly reconciled and rekindled their old relationship.

Porter was pregnant with twins when she learned that another woman was pregnant with Diddy’s child. Porter told the media at the time that she felt betrayed.

In July 2007, Porter ended his relationship with Diddy. “I have made the decision to end this relationship in the best interests of myself, Sean and our family. I look forward to moving on with my life and career and wish him success, health and happiness in his life and in his love life. We will remain friends and devoted parents to our children,” Porter said in a statement at the time.

However, they remained close friends until her death in 2018 from pneumonia.

Jennifer Lopez

Diddy began a relationship with Lopez in 1999 and the two dated for two years before breaking up in 2001. Jennifer Lopez said the reason for their split was Diddy’s infidelity. One of the memorable moments between Diddy and Lopez was when they attended the Grammy Awards together in 2000, where the beauty wore the famous blue Versace dress.

Diddy once had many compliments for his ex-girlfriend and said that she was one of the greatest loves of his life.

Sarah Chapman

Diddy and businesswoman Chapman have a strange relationship. The two have confirmed that they are not dating and are just friends, but they have a daughter together. The baby was born while Diddy was still dating Porter. Despite a rocky start to their parenting journey, Diddy has maintained a close relationship with Chapman as they raise their daughter, Chance.

Cassie

After splitting with Porter in 2007, Diddy began a relationship with singer Cassie, real name Cassandra Ventura. The two maintained an on-again, off-again relationship for a decade before officially calling it quits in 2018.

In November 2023, Cassie accused Diddy of raping and abusing her throughout their relationship. In the complaint, Cassie said she met Diddy when she was 19 and he was 37. She alleged that shortly after, Diddy had “complete control” over her life. She was forced to accept Diddy’s advances out of fear of retaliation if she refused.

The complaint also alleges that Diddy physically abused her, stomping on her face and forcing her to hide in a hotel room for a week until the bruises healed. Cassie also claims that after she decided to break up in September 2018, Diddy raped her.

Lori Harvey

In July 2019, Diddy and Lori Harvey were rumored to be dating when they were seen walking together through the SoHo neighborhood of New York City. A month later, they were seen vacationing in Italy with Harvey’s parents, Marjorie and Steve Harvey. However, just a few months later, it appeared that the two had broken up when Harvey unfollowed Diddy on social media a few days after he was seen having dinner with another woman.

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

Yung Miami

Diddy and City Girls rapper Yung Miami were rumored to be in a relationship in 2021 but didn’t confirm it until 2022. Appearing on Yung Miami’s podcast, when asked ‘What are we?’ Diddy replied: “We’re dating.” In another interview, the rapper said she was “single” but they were dating.

“We’re dating. We’re single, but we’re dating. People don’t know what dating means. He’s single, I’m single, but we’re dating,” she said.

In 2023, the two attended the 2023 Met Gala together. When host La La Anthony asked about the couple, Diddy explained that they “didn’t put a title” on their relationship. In August 2024, Yung Miami told The Cut that she was single and that Diddy “wasn’t her man.”

Dana Tran

Although Diddy never confirmed his relationship with Dana Tran, the two welcomed a baby girl named Love in October 2022. According to experts, Diddy and Dana Tran are not in a romantic relationship, the connection between the two is their daughter Love.