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Josh Groban, January Jones, Cameron Diaz, Matt Dillon, Kelly Preston, George Clooney

E. Charbonneau/WireImage for Vanity Fair Magazine, Steve Granitz/WireImage, Jim Smeal/WireImage

Who did Sarah Jessica Parker get cozy with before marrying Matthew BroderickCan you imagine Chris Pratt with anyone else but wife Anna Farris? And who called Ashton Kutcher a bad ex-boyfriend? (Hint: She's now a Mad Men star!)

Whether they flew under the radar or paired up before you were even put on this earth, you might have missed these surprising celebrity couples that once were.

From Johnny Depp and Ellen Barkin to Kate Hudson and Dax Shepard, we're bringing you a list of Hollywood pairings from the ‘80s, ‘90s and beyond that might make you stop and say, ‘What?! They dated?!"