Ashton Kutcher had eyes for America’s Sweetheart as a teen, and even waged money that he would make Jennifer Aniston his. 

“I made a bet when I was in high school — you have to imagine, I’m living on a farm in the middle of America, right,” Ashton explained on The Graham Norton Show. “And really having no chance of having a happy life. And I’ve sort of succumbed to this, so the best ideas I have are sitting around in basements making bets about what we would do someday.”

“So I make a bet with my buddy, I’m probably 17 years old. I say to him, ‘I bet you a thousand dollars that someday I will go on a date with Jennifer Aniston,’” he continues. “I’m 17 years old in Iowa and she’s like on my screensaver on my computer at this time, right? And he’s like, ‘You’re on, someday.’”

That day came when, four or five years later, Ashton asked Jennifer — with then-husband Brad Pitt’s blessing — out for pizza. She understandably shrugged off his advances, but the two could now be considered (wait for it) friends.


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