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Well, this is awkward….

The Most Awkward Celebrity Couples Of All-Time

Fame and love don’t really mix in our lovesick society where celebrity relationships crumble before they really start. It may seem easy for the rich and famous to find love BUT it’s clearly not based on the very awkward, mismatched and downright mind-boggling celebrity couples of the past several years.

Hit the jump for a (hilarious) gallery of the most awkward celebrity couples…ever.

Kim Kardashian & Kris Humphries

Beyonce & Jay Z

Nick Cannon & Mariah Carey


Mila Kunis & Macaulay Culkin

Rihanna & Drake

Continue Slideshow

Pharrell & Helen Lasichanh

Jennifer Lopez & Ben Affleck

Angelina Jolie & Billy Bob

Usher & Tameka Raymond Foster

Simon Cowell & Carmen Elektra

Geoffrey Arend & Christina Hendricks

Prince William & Kate Middleton

Mary-Kate Olsen & Olivier Sarkozy

Khloe Kardashian & French Montana (WHO?)



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