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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.

Sean Combs is a well known musician, producer and designer.

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During a long break between Diddy and Kim Porter he dated Jennifer Lopez.

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.

Sean “Diddy” Combs Rumored Girlfriend Diana Bianchi 2008 She claimed the two had an affair at the recording studio though Diddy denies this.

July 2008 - July 2008Sean Combs signed Cassie to his Bad Boy label, and that sparked romance rumors in the summer of 2008.