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Celebrities never fail to surprise us. Whether it’s risky movie roles, unexpected career moves or shocking confessions. But let’s be honest for a moment: what we’re always dying to know is who’s dating who and who’s just broke whose heart. While the mammoth of celebrity couples, Brangelina, shocked us with the announcement of separation, we’d like to take a moment and remember the couples we can’t believe matched in the first place.

image: Getty Images
image: Getty Images

20. Drew Barrymore and David Arquette

David Arquette certainly had fun on the set of the Scream trilogy. Not only did he marry his on-screen love interest Courteney Cox, but he recently revealed that he had a thing going on with Drew Barrymore, too. Although sources reveal Arquette and Barrymore dated long before they had to run away from the Ghostface together — they were an item in 1991.

Image: Getty Images
Image: Getty Images

19. Jessica Simpson and Jensen Ackles

Apparently the Supernatural star was “Irresistible” for Jessica Simpson as they dated back in the ’90s. The romance didn’t last long long — Simpson later revealed that Ackles cheated on her with LeAnn Rimes.

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Image: Getty Images
Image: Getty Images

18. Sarah Jessica Parker and Robert Downey Jr.

Long before Downey Jr. was saving the world as Iron Man and Parker was clicking her Manolo Blahnik’s as Carrie Bradshaw, they were the tightest Hollywood couple from 1984 to 1991, before Downey’s addiction and misbehaving took the best of their relationships. Last year they had a reunion meeting, which gave both much-needed closure.

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