Inside P Diddy’s wild relationship history: From his 17-year age gap with ex Cassie to a fling with JLo – amid sex trafficking and racketeering charges
P Diddy, Sean ‘Diddy Combs, is currently awaiting trial after being charged with sex trafficking and extortion.
On Tuesday, authorities released the indictment, which charges Diddy, 54, with extortion, sex trafficking and transportation for the purpose of prostitution.
His arrest came nearly a year after his ex-girlfriend Cassie settled a blistering $30 million lawsuit with him in November, in which she accused the mogul of rape, sex trafficking and repeated physical abuse during their ten-year relationship.
In May the release of gruesome leaked CCTV footage showing him beating her up in a hotel hallway in 2016.
Diddy pleaded not guilty during a bail hearing, where his legal team failed to secure his freedom by offering the court a $50 million bail package.
As the producer awaits trial, MailOnline takes a look at his wild relationship history, which has seen the musician have romantic liaisons with the likes of supermodel Naomi Campbell and model Lori Harvey…
Love life: The rapper, who is commonly known as P Diddy, Puff Daddy or more commonly Diddy, has a colorful dating history
Bombshell claims Diddy with Cassie at the premiere of ‘The Perfect Match’ at ArcLight Hollywood on March 7, 2016 in Hollywood, California
Misa Hylton-Brim
Happy family? Misa and Diddy welcomed their son Justin Combs (center) shortly after, in 1993
The New York fashion designer was born on January 6, 1973 and is one of Diddy’s first girlfriends.
When Diddy appeared on The Wendy Williams Show in 2017 and candidly told the host that he had multiple children with three different women.
He told People Magazine: ‘I met them all in the same year’.
Misa Hylton-Brim was the first mother of his children. They met in the 90s when Misa was a budding stylist at just 17 years old, but has since gone on to have a successful fashion career and even had a cameo in The Notorious BIG’s ‘Big Poppa’ music video.
When Diddy interned at Uptown Records, Misa helped him style Jodeci, one of the R&B acts he mentored.
Misa did so well that she was hired to style Mary J. Blige, who was then just an up-and-coming artist. The couple began dating and welcomed their son Justin Combs shortly after, in 1993.
Kimberly Porter
Playboy: Kim Porter and Diddy at his birthday party in Los Angeles on November 21, 2015
Diddy had an on-again, off-again relationship with actress Kimberly Porter, who tragically passed away in 2018 at the age of 47 after battling a serious bout of pneumonia.
Kim was also a model and was born on December 15, 1970 in Georgia.
Her credits include: Single Ladies, The Brothers and Mom, I Want to Sing, Wicked Wicked Games, Law & Order and Diddy’s show, I Want to Work for Diddy.
They dated for 13 years, met in 1994, and have three children: son Christian and twin daughters Jessie and D’Lila.
Diddy adopted her son from a previous relationship, Quincy, born in 1991 to his musical rival, singer Al B. Sure!
But just months before his twins were born, Diddy cheated on Kim with Sarah Chapman, who gave birth to another daughter for the rapper.
Jennifer Lopez
Dangerous duo: Jennifer Lopez and Diddy were arrested on Valentine’s Day 2001 for a nightclub shooting that left them embroiled in a drama
In 1999, Diddy and Hollywood A-lister Jennifer Lopez dated for two years. Their much-discussed relationship regularly made tabloid headlines.
However, their romance came to an abrupt end on Valentine’s Day 2001, when a shooting occurred at a nightclub, leaving the two embroiled in drama.
The pair were arrested, but quickly acquitted of all charges.
Jennifer later admitted that she was aa different vision for her family than the one Diddy had.
Casandra Ventura
Long-term relationship: Cassie filed a lawsuit against Combs on November 16, 2023, alleging “rape and repeated physical abuse over the course of approximately a decade”
Lawsuit: Cassie’s lawsuit alleges severe physical, emotional and sexual abuse
Combs was primarily romantically involved with his girlfriend of 11 years, R&B singer Cassie.
They were in a relationship from 2007 to 2018, after meeting in 2005 when she was 19.
Their on-again, off-again relationship was initially secret, but in 2012 their romance became public knowledge.
Cassie ended her relationship after she had enough of Diddy’s lack of commitment. She has since moved on and is happily married to personal trainer Alex Fine, with whom she has two children.
Cassie filed a lawsuit against Combs on November 16, 2023, alleging “rape and repeated physical abuse over the course of approximately ten years.”
She alleged that shortly before their relationship ended, Diddy broke into her home and raped her.
Her complaint details how he allegedly drugged, intimidated and forced her to have sex with male sex workers in front of him during their relationship.
Young Miami
Yung Miami: The singer famously shares her partner with other women
Yung Miami is the 29-year-old singer who is part of the duo City Girls who went public with her romance with Diddy in June 2022 and told the public about their polyamory.
During the 2022 BET Awards, Yung Miam held up a bright red sign that read “Go Papi” as the music mogul delivered his acceptance speech.
It seems like the two are getting along very well and are set to spend New Year’s Eve 2023 together at a luxury resort in St. Barts.
The brunette beauty placed cozy photos with the rapper to commemorate the holiday. She wrote: ‘365 more days around the world with you. Happy New Year!’
Lori Harvey
Beauty: Model Lori Harvey has been linked to rapper Diddy in the past
Diddy and model Lori Harvey, Steve Harvey’s adopted daughter, have been rumored to be in a relationship since July 2019.
The two lovebirds were spotted in various locations around the world, including Italy, Mexico and his hometown of New York City.
However, the two have never publicly confirmed their relationship, and neither has stepfather Steve could not confirm the matters.