1. Natassia Malthe
![Royal Film Premiere Of The Other Boleyn Girl - London](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631748882494.jpg?quality=80&strip=all&w=336&crop=0%2C0%2C100%2C480px)
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](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14419267421157.jpg?quality=80&strip=all&w=319&crop=0%2C0%2C100%2C480px)
Queen video vixen ‘Superhead’ says that she hooked up with Diddy once upon a time
3. Naomi Campbell
![Deleon Tequila Launch Party](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631741645238.jpg?quality=80&strip=all&w=378&crop=0%2C0%2C100%2C480px)
Naomi and Diddy were once “The Ultimate Power Duo” according to ‘Vogue’
4. Jennifer Lopez
![1999 MTV Music Awards Arrivals](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631739381.jpg?quality=80&strip=all&w=505&crop=0%2C0%2C100%2C480px)
These two were really the ultimate power couple of the late 1990s
5. Misa Hylton
![Ciroc Vodka Presents Sean 'Diddy' Combs' Birthday Celebration](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631738459475.jpg?quality=80&strip=all&w=322&crop=0%2C0%2C100%2C480px)
Misa is the mother of Diddy’s oldest child, Justin
6. Cassie
![Premiere Of Lionsgate's 'The Perfect Match' - Arrivals](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631737155593.jpg?quality=80&strip=all&w=410&crop=0%2C0%2C100%2C480px)
Diddy’s current boo
7. Penelope Cruz
![Giorgio Armani Prive in L.A. - Inside](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631736223476.jpg?quality=80&strip=all&w=364&crop=0%2C0%2C100%2C480px)
Penelope starred in Diddy’s fashion campaigns but did they go the extra mile?
8. Cameron Diaz
![The 80th Annual Academy Awards - Arrivals](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631735619353.jpg?quality=80&strip=all&w=335&crop=0%2C0%2C100%2C480px)
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](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631734799172.jpg?quality=80&strip=all&w=629&crop=0%2C0%2C100%2C480px)
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](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631734019537.jpg?quality=80&strip=all&w=326&crop=0%2C0%2C100%2C480px)
Kim is the mother of three of Diddy’s children
11. Tracey Edmonds
![88th Annual Academy Awards - Arrivals](https://ioneglobalgrind.staging.go.ione.nyc/wp-content/uploads/sites/16/2016/05/14631732624279.jpg?quality=80&strip=all&w=366&crop=0%2C0%2C100%2C480px)
These two were linked together even though Tracey maintains that they are “just friends”