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Who Dated Who? Celebrity Romances You Didn’t Know About

Lance Armstrong Oprah Winfrey interview
George Burns/Oprah Winfrey Network via Getty Images

No, Oprah and Lance Armstrong didn’t date, but we think you’ll surprised to find out who they DID date!

Did you know that Owen Wilson and Sheryl Crow used to date? How about Lance Armstrong and Ashley Olsen? This one skeeves me out… Yes, Roger Ebert and Oprah Winfrey dated! Could you imagine those two knocking the boots?

I’ve been reporting celebrity gossip for years and a lot of these hook ups are new news to me. You might think I’m making these odd Hollywood pairings up, but they absolutely happened. How about Winona Ryder and Jimmy Fallon? You guessed it! They hooked it up in 2002. You Oughta Know singer Alanis Morrisette dated Hollywood heart throb Ryan Reynolds from around 2002 – 2007.

The Huffington Post did the dirty work and went through years of photos to find proof of these low key hook ups! Check ‘em out here!

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