Sean Combs » Dating History

Complete list of Sean Combs dates, listed in chronological order.

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Karrine Steffans
Karrine Steffans and Puff Daddy unknown date
Misa Hylton-Brim
Puff Daddy and Misa Hylton-Brim September 1992 - 1995
Sean and Misa (who is now a designer) were college sweethearts. They had a child, named Justin Dior, in December 1993, and eventually went their separate ways. These days, she and Diddy are still in touch, and Misa has dished about his other girlfriends in interviews over the years. [more]
Sarah Chapman
P. Diddy and Sarah Chapman 1993 - 2009
Diddy and Sarah Chapman were friends for years and never publicly admitted to dating, especially since the music mogul was in a longterm relationship with Kim Porter during this time. It`s hard to say for sure if these two actually had a relationship, but they definitely had relations: Sarah gave birth ... [more]
Kim Porter
Puff Daddy and Kim Porter May 1994 - July 2007
Sean and Kim dated on-and-off for over a decade. They famously broke up in 1999 and battled over child support for their son, and Diddy dated Jennifer Lopez for two years. Then, Kim and Sean reconciled in 2003 and were together for another almost 4 years. They had twin daughters in 2006 and called it ... [more]
Lil' Kim
Sean Combs and Lil' Kim 1997 - 1998
Jennifer Lopez
Jennifer Lopez and Puff Daddy August 1999 - February 2001
While Jennifer Lopez and Sean "Diddy" Combs didn`t publicly acknowledge their relationship until September, 1999, they were dating for months before that. Lopez was with Combs the night that his entourage got into a night club argument in New York that ended in gun fire. While Lopez was cleared ... [more]
Emma Heming
Sean Combs and Emma Hemming 2001
Emma Heming and Sean Combs became an item after Sean`s break-up with Jennifer Lopez. He posed with her in a photo spread for `Details` magazine in 2001. [more]
Sky Nellor
Sky Nellor and Sean Combs 2002 RUMOR
Diddy was rumored to be cheating on Kim Porter with Sky when they were on tour together. [more]
Alicia Douvall
Sean Combs and Alicia Douvall 2002
British glamour model Alicia Douvall told news outlets in 2002 that she was pregnant, and Diddy was the dad. She claimed they`d had a one-night stand, but nothing was ever confirmed. Apparently he wasn`t the first celeb she allegedly bedded. [more]
Naomi Campbell
Puff Daddy and Naomi Campbell 2002
Naomi and P. Diddy dated briefly in 2002, but they remained friends after the split. [more]
Cassie Ventura
Cassie Ventura and P. Diddy May 2006
Sean Combs signed Cassie to his Bad Boy label, and that sparked romance rumors in the summer of 2006. There was even engagement buzz for a while! Both parties denied the relationship. "We are not together, but we are definitely friends," she said. [more]
Sienna Miller
Puff Daddy and Sienna Miller February 2007
Aubrey O'Day
Aubrey O'Day and Puff Daddy April 2007 RUMOR
Sean and Aubrey worked together (she was one of the winners of his reality show "Making the Band") and when the Danity Kane singer packed on a few pounds, the tabloids automatically assumed she was prego, and Diddy was the daddy. Both camps denied the claims, and Aubrey issued a statement on ... [more]
Diana Bianchi
Sean Combs and Diana Bianchi 2008
Diddy denied up and down that he slept with Diana Bianchi, the young woman who had an affair with Christie Brinkley`s husband, Peter Cook. A source told the "National Enquirer" she and Diddy had an affair after meeting at his recording studio. [more]
Cameron Diaz
Cameron Diaz and Sean Combs December 2011 RUMOR
Cameron Diaz and Sean “Diddy” Combs are bonding over more than just a “movie project” — they were caught kissing Saturday night at PH-D at the Dream Downtown Hotel. Spies said the blond actress, who split with Yankee slugger Alex Rodriguez in September, started the night ... [more]
Kate Upton
Kate Upton and Sean Combs 2013 RUMOR

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