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Sean Combs is a well known musician, producer and designer. He has been known by many names over the years, including Puff Daddy, Puffy, P. Diddy and today he goes by Diddy. While his music career may not be as interesting as it once was, he has a very interesting dating history that is worth exploring, even though no woman has ever snagged the title of Sean “Diddy” Combs wife.

Sean “Diddy” Combs Girlfriend Misa Hylton Brim 1993 to 1995

These two were college sweethearts and dated for a few years. In this time they had a child together, a son named Justin Dior in December of 1993. Even though they broke up not even two years later, they two have remained friends since. They even share common interests today as both work in clothing design.

Sean “Diddy” Combs Girlfriend Kim Porter 1996 to 2007

These two dated on and off for more than a decade. When they got into the relationship, each had a son from a previous relationship. Diddy took on the role as the informal step father to Porter’s son Quincy. In 1998 they had a son named Christian together. Then in 2006 they had twin daughters named D’Lila Star and Jessie James. The final time they broke up there was speculation that it was because of Diddy’s affair which produced a child.

Sean “Diddy” Combs Rumored Girlfriend Lil’ Kim 1997 to 1998

There were rumors that these two had an affair for almost a year while he was with Kim Porter but this was never substantiated.

Sean “Diddy” Combs Girlfriend Jennifer Lopez September 1999 to February 2001

During a long break between Diddy and Kim Porter he dated Jennifer Lopez. There were rumors the two had been seeing each other for months before they went public with their relationship. In fact, Lopez was with Diddy the night of the gun fire incident in New York. Sources say that the legal turmoil over clearing his name is what caused a rift in their relationship leading to their breakup.

Sean “Diddy” Combs Girlfriend Emma Heming Willis 2001

These two dated briefly in 2001 after the relationship with Jennifer Lopez ended and before he got back together with Kim Porter. Though they were only together for a short period, it was long enough to do a photo shoot with.

Sean “Diddy” Combs Girlfriend Naomi Campbell 2002

There was a brief relationship between Diddy and the supermodel in 2002, though it was short lived. They remain close friends to this day.

Sean “Diddy” Combs Rumored Girlfriend Alicia Duvall 2002

In 2002 the British supermodel claimed to have a one night stand with Diddy that got her pregnant. Diddy disputed these allegations and she miscarried so the paternity was never confirmed.

Sean “Diddy” Combs Girlfriend Sarah Chapman 2004 to 2006

There is not much known about Sarah Chapman except that Diddy had an affair with her while dating Kim Porter. They had a daughter named Chance together in 2006. Since then there have been a few rumored girlfriends of the music mogul though none have been confirmed.

Sean “Diddy” Combs Rumored Girlfriend Aubrey O’Day 2007

These two worked together on making the band and rumors flew that they were together. When she gained a few pounds, rumors spread she was pregnant with his baby.

Sean “Diddy” Combs Rumored Girlfriend Cassie 2008

There were rumors in 2008 that these two were together when he signed her to his Bad Boy label. There were even rumors they were engaged, though both said they were simply friends.

Sean “Diddy” Combs Rumored Girlfriend Diana Bianchi 2008

She claimed the two had an affair at the recording studio though Diddy denies this.