When Jennifer Aniston Almost Dated Ashton Kutcher

On 22nd February, Jennifer Aniston made an appearance on the Spanish TV show El Hormiguero in Madrid. The actress, who recently got a haircut and was wearing glasses, was there to promote her film Just Go With It alongside co-star Adam Sandler.

In a recent interview on The Graham Norton Show, Ashton Kutcher shared a surprising story from his high school days.

Apparently, he made a bet with a friend that he would one day go on a date with none other than Jennifer Aniston. As fate would have it, he did eventually cross paths with Jen when she was still married to Brad Pitt.

But before making a move, Ashton asked for Brad’s permission to ask his wife out. To his surprise, Brad gave his blessing and encouraged him to go for it. Sadly, Jen turned him down, but the two have since become good friends.

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