Inside Diddy's Long Dating History

Everything to know about Diddy's personal life amid bombshell lawsuit, accusing the rapper of rape and assault!  

Rap mogul Puff Diddy is the latest Hollywood titan to face serious allegations of rape and assault. To make the scathing case worse, the series of horrific accusations comes from none other than his longtime partner, Cassie Ventura. Here's a trip down the rapper's romantic history and his ongoing personal affairs as the world turns its focus on Diddy, who has maintained a relatively reputable image.  

Born Sean Love Combs on November 4, 1969, in Harlem, NYC, his illustrious career in the industry spans over three decades. Sean's journey started with an internship with Uptown Records in 1990. Three years in the business, Combs was already overseeing his own label, Bad Boy Entertainment, and locking a $100 million worth of deals. Throughout his career as a record producer and executive, Diddy is credited for cultivating artists such as Usher, Mary J, and more.  

Inside Diddy's Dating History!     

Diddy loves a beautiful woman by his side and his long, star-studded romantic history is the ultimate testament. The music connoisseur has been dabbling in the dating pool for a long time and in the process, has fathered six children with different women.   

Diddy's public earliest relationship with fashion stylist Misa Hylton-Brim resulted in the birth of his firstborn, Justin. Although the pair's romance was short-lived and did take a serious turn after their son's birth, the two currently share a cordial bond. The rap mogul had the most notable relationship with actress Kim Porter, with whom he was on and off, from 1994 to 2007.  

Porter, who tragically died from lobar pneumonia in 2018, was with singer Al B. Sure when she met Diddy in 1994. The pair gradually started a family, welcoming three kids, Christian, D’Lila, and Jessie as they delved into their decade-long bumpy romance. Sean poured his heart out for Kim in his latest album The Love Album: Off The Grid, which also featured Babyface and John Legend.   

Diddy had a brief affair with Sarah Chapman while he was navigating a bumpy romance with Kim. The affair put much strain on the rapper's committed relationship with Kim as he fathered a daughter, Chance, with Chapman. Sean's pairing with Jennifer Lopez in the late 90s and early 2000s took many by surprise.  

While Diddy was already knee-deep in his stellar music career, JLo was yet to find her footing in the glamour world of possibilities. The singer-turned-actress later reflected on her relationship with Diddy, concluding that Diddy's formative influence in her early career was probably the main factor behind their romance.   

"He became kind of a mentor to me in that moment," JLo explained, adding, "We had this kind of crazy, tumultuous relationship that ended in a bang." The duo's romance reportedly lasted on and off from 1999 to 2001. The Grammy-winning rapper started dating Cassie Ventura in 2007.  

The duo's romance was no less tumultuous than Diddy's former relationships, with the two breaking it off time and again until their final split in 2018. As per insiders, Cassie, who recently accused the rapper of rape, assault, and even sex trafficking in a lawsuit. The estranged duo has reportedly reached an undisclosed settlement.   

Diddy's romantic history also consists of brief affairs with divas such as models Gina Huynah and Lori Harvey, both of whom were linked with the rapper in 2019. Over the years, the Grammy winner has also sparked dating rumors with actress Cameron Diaz, and Naomi Campbell.  

Who is Diddy Dating?  

The rap mogul's love life seems to be getting more confusing each year. Diddy was linked with City Girls rapper Yung Miami in 2021 and it wasn't long before the two confirmed their liaison on Miami's podcast, Caresha, Please. Things only got complicated from there on as both rappers asserted their open relationship on several occasions.   

Diddy was in an open relationship with rapper Yung Miami! 

"People don't know what dating means. He's single, I'm single, but we're dating," Miami said while echoing Diddy's statements. The record producer even tapped Yung to appear in his Gotta Move On music video, but perhaps the collaboration was nothing more than a collegial feat as the rapper would soon announce the birth of his youngest kid with another woman.  

"I'm so blessed to welcome my baby girl Love Sean Combs to the world," the rapper tweeted while keeping the identity of his daughter's mother a secret. It was shortly revealed that Sean had his daughter with a cybersecurity professional, Dana Tran, who so far remains a mystery.  

Since the news of Diddy welcoming a kid with a new woman got out, the rapper and Miami have had a tumultuous relationship in the public, with the City Girls rapper even embroiling in a nasty internet feud with Diddy's ex, Gina Huynh, who trolled Yung by calling her Diddy's side chick.  

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