1. Natassia Malthe

Royal Film Premiere Of The Other Boleyn Girl - London Source:Getty

Rumors have flown around that Diddy had flown this model/actress around the globe

2. Karrine Steffans

Taschen Hosts 'Big Penis Book 3D' Launch Party Source:Getty

Queen video vixen ‘Superhead’ says that she hooked up with Diddy once upon a time

3. Naomi Campbell

Deleon Tequila Launch Party Source:Getty

Naomi and Diddy were once “The Ultimate Power Duo” according to ‘Vogue’

4. Jennifer Lopez

1999 MTV Music Awards Arrivals Source:Getty

These two were really the ultimate power couple of the late 1990s

5. Misa Hylton

Ciroc Vodka Presents Sean 'Diddy' Combs' Birthday Celebration Source:Getty

Misa is the mother of Diddy’s oldest child, Justin

6. Cassie

Premiere Of Lionsgate's 'The Perfect Match' - Arrivals Source:Getty

Diddy’s current boo

7. Penelope Cruz

Giorgio Armani Prive in L.A. - Inside Source:Getty

Penelope starred in Diddy’s fashion campaigns but did they go the extra mile?

8. Cameron Diaz

The 80th Annual Academy Awards - Arrivals Source:Getty

It is alleged that Diddy said Cameron is “the one that got away”

9. Sienna Miller

2007 Park City - MySpace Nights at Tao - Day 2 - Inside Source:Getty

These two were spotted frequently hanging out together in 2007

10. Kim Porter

Sean 'Diddy' Combs Exclusive Birthday Celebration Presented By CIROC Vodka In Beverly Hills Source:Getty

Kim is the mother of three of Diddy’s children

11. Tracey Edmonds

88th Annual Academy Awards - Arrivals Source:Getty

These two were linked together even though Tracey maintains that they are “just friends”

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