Sean ‘Diddy’ Combs’ Past Relationships Flashback During Investigation

Content warning: This article contains accusations of rape and abuse.

Sean “Diddy” Combs and his list of highly publicized relationships are under scrutiny again following his arrest in New York on Monday.

Combs was arrested on September 16 at the Park Hyatt Hotel in Manhattan, and a federal indictment was unsealed the next day charging him with extortion, human trafficking and soliciting prostitution.

The news comes after Combs faced multiple civil lawsuits alleging sexual assault, human trafficking and illegal distribution of weapons and drugs.

Combs’ attorney said Tuesday he does not intend to plead guilty.

“He will fight this with all his energy, all his might and the full confidence of his lawyers,” attorney Marc Agnifilo said in Manhattan federal court.

Last fall, the 54-year-old rapper settled a lawsuit filed against him by his ex-partner and “Me & U” singer Cassie, whose full name is Casandra Ventura. The pair dated from 2007 to 2018, and Cassie’s lawsuit accused Diddy of various abuses, including rape.

The music producer denies any wrongdoing and on November 17, he and Cassie announced a settlement.

However, recent allegations against Combs have sparked renewed interest in his past relationships and personal life.

Combs is the father of seven children with four different women, and some of his ex-wives, like Jennifer Lopez, have had careers that have surpassed his own.

Here are the women the rapper and music mogul has dated and had children with:

Hylton Bowl

Diddy’s first brush with public interest in his love life came in the early ’90s, when he was linked to designer Misa Hylton.

According to a report in The New York Times, Hylton was working on projects for high-profile R&B and rap stars such as Lil’ Kim and Mary J. Blige when Diddy founded his record label, Bad Boy Records, in 1993.

Hylton gave birth to Diddy’s son, Justin Dior, in 1993; however, in 2006, their relationship began to deteriorate.

That same year, the Associated Press reported that a lower court ordered him to pay his wife more than $19,000 a month in alimony.

Regardless of their differences over child support, Combs and Hylton have appeared cordial over the years. In 2019, Hylton attended Diddy’s 50th birthday party.

Jennifer Lopez

Although Diddy and Jennifer Lopez dated for only two years, between 1999 and 2001, there is no denying that their relationship has become a permanent part of the pop culture iconography of the early 21st century.

During their relationship, the couple ruled the red carpet, attended one of the first famous all-white parties in the Hamptons and attended the 42nd Grammy Awards, where Lopez wore her iconic Versace dress.

However, in 2001, the couple was struggling with a long-term crisis that had its origins in their relationship in 1999, when they witnessed a shooting at a Manhattan nightclub.

Diddy was later arrested and charged with weapons violations and other charges, according to The New York Times.

In May 2001, The New York Times reported that the charges against Diddy had been dropped and he and Lopez were no longer together.

Kim Porter

Diddy and Porter had an on-and-off relationship throughout the 1990s, but ultimately ended it in 2007 after the birth of their three children.

The couple welcomed their first child together, Christian, in April 1998. However, Diddy helped raise Porter’s son — Quincy Taylor Brown — from her previous relationship with singer Albert Joseph Brown III, known professionally as Al B. Sure. Quincy was born in 1991.

In 2006, Combs and Porter welcomed twins, Jessie and D’Lila Combs.

While pregnant with the twins, Porter learned that Combs was expecting another child with her co-star Sarah Chapman.

Porter died of lobar pneumonia in 2018. A year later, People magazine reported that Combs expressed regret that he never married the woman with whom he claimed to have had an “inexplicable relationship.”

Sarah Chapman

Diddy and Sarah Chapman welcomed their son, Chance Combs, in 2006.

According to People magazine, the couple knew each other for years before Chapman became pregnant while Combs was still in a relationship with Porter.

Porter gave birth to her and the Combs twins five months after Chapman gave birth to Chance.

These days, Chapman and Diddy remain connected through their daughter and their business. According to her Instagram page, Chapman currently works for Diddy’s company, Combs Global.

In September 2023, the rapper wished Chapman a happy birthday by posting on his Instagram account.

“Happy birthday Sarah! @callmepumpkin,” he wrote. “We thank God for you every day! We are so grateful to have you in our lives! We love you.”

Kasia

In 2007, after Diddy’s relationship with Porter broke up, he began dating singer Cassie.

Cassie was 19 when she met Diddy, who was then 37 and the head of Bad Boy Records, with which she had a music contract.

The couple began an on-again, off-again relationship, and attended events together, including the Met Gala in New York. They had no children together and eventually ended their relationship in 2018.

However, things weren’t completely over between the two. In November 2023, Cassie filed a legal complaint against Diddy and accused him of exercising “total control” over their nearly decade-long relationship, according to NBC News.

Cassie claimed that after trying to break up with Diddy in 2018, he forced her into sex and raped her. She also claimed that throughout their relationship, the rapper punched, kicked, hit and stomped on her.

Combs’ lawyer responded to the allegations, saying Diddy has “categorically” denied the allegations.

When the couple wrapped up their trial on Nov. 17, Combs’ attorney Ben Brafman said the rapper had not admitted any wrongdoing.

“Mr. Combs’ decision to settle does not in any way undermine his emphatic denial of the claims,” he said in a statement. “He is pleased that they have reached a mutual agreement and wishes Ms. Ventura all the best.”

You can read more about the chronology of their relationship here.

Dana Tran

Little is known about the scope of Diddy’s relationship with Dana Tran, a cybersecurity expert with whom he welcomed a daughter named Love in October 2022.

In December 2022 shared a post on X Welcome little one.

“I am so happy to welcome my baby girl Love Sean Combs into the world,” the post reads. “Mama Combs, Quincy, Justin, Christian, Chance, D’Lila, Jessie and I love you all so much! God is the Greatest!”

Nearly a year after Love’s birth, Tran celebrated the milestone with an Instagram post featuring a family photo of the couple and Love.

“A year of love,” the post’s caption reads.

This article was originally published on TODAY.com