YOU MAY NOT KNOW–From Breakup With Jennifer Lopez to the Tragic Death of Partner Kimberly Porter, Diddy’s Dating Life Has Seen Many Ups and Downs

From JLo to heartbreak,

s love life could give Shakespeare a run for his money!

Sean Combs has been involved in numerous high-profile relationships, including with celebrities like Jennifer Lopez and Cassie Ventura.

Diddy

Since his ascent to fame in the 1990s, Diddy, aka Sean Combs, has been involved in a number of high-profile relationships. Throughout his career, the No Way Out hitmaker has been associated with a number of well-known celebrities, including Jennifer Lopez and Cassie Ventura. Kimberly Porter was the woman he dated for the longest, beginning in the 1990s and ending in 2007.

Of course, dating has not always been easy for the father of seven children. His public relationship with Lopez and the tragic death of his partner Porter were the starting points of this. The music mogul, 54, has had a number of ups and downs in his love life, prompting fans to speculate about his love life at every turn.

Diddy in a still from his single Bad Boy For Life

But the relationship that lasted ten years with the late Porter—the mother of three of his seven biological children—seems to have given him the biggest emotional lift of his life.

From J.Lo to Kimberly Porter: The Women Behind Diddy’s Heartache
During his early career as a musician in the 1990s, Sean Combs, aka Diddy, got romantically involved with fashion designer Misa Hylton. When the latter was hired by music group Jodeci, he helped her land her big break. In March 2023, she told BET:

“We were dating at the time and he had just went from intern to A&R.”

After that, in 1994, Combs began dating Kimberly Porter, who passed away on November 15, 2018. Diddy said to Essence,“The first time I saw her, she was at the studio with her ex-boyfriend”, alluding to singer Al B. Sure!

Although Porter maintained control, Diddy’s love was not always under his control. In 1999, the late model and rapper broke up as the latter started dating Jennifer Lopez. Before calling it quits in 2007, Diddy and Porter reignited their romance in 2003.

“The Puffy era was just kind of a crazy, heightened tJennifer Lopez in This Is Me..Nowime in my life. You know, Puffy and I both grew up in the Bronx.” 

Jennifer Lopez in This Is Me..Now

They parted ways in 2001. Diddy’s publicist, Nathalie Moar, reportedly told ABC News that the rapper “confirmed that he and his love, Jennifer Lopez, have, in fact, broken up.”

Combs and Cassie Ventura had an eleven-year relationship that lasted from 2007 to 2018. Diddy and Cameron Diaz had a brief romance in 2008, but it was more of a fleeting relationship between two ‘90s icons. According to a 2014 Us Weekly article, Diddy said, “If I could turn back time, things would be different”, in response to a discussion regarding Cameron and Benji Madden’s relationship.

Things Get Worse For Meek Mill After Lawsuit Exposes His Alleged Romance With Diddy
From rumored relationships with other celebrities to his search for love in the aftermath of Porter’s death, Diddy’s romantic pursuits have been closely watched by the public.

They parted ways in 2001. Diddy’s publicist, Nathalie Moar, reportedly told ABC News that the rapper “confirmed that he and his love, Jennifer Lopez, have, in fact, broken up.”

Combs and Cassie Ventura had an eleven-year relationship that lasted from 2007 to 2018. Diddy and Cameron Diaz had a brief romance in 2008, but it was more of a fleeting relationship between two ‘90s icons. According to a 2014 Us Weekly article, Diddy said, “If I could turn back time, things would be different”, in response to a discussion regarding Cameron and Benji Madden’s relationship.

Things Get Worse For Meek Mill After Lawsuit Exposes His Alleged Romance With Diddy
From rumored relationships with other celebrities to his search for love in the aftermath of Porter’s death, Diddy’s romantic pursuits have been closely watched by the public.