Jon Stewart dated Jennifer Aniston in the nineties

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Jennifer Aniston

It was only one date, though it kindled a bi-coastal romance so steamy, so deep, that they never contacted each other for another fifteen years.

Last night, Jennifer Aniston appeared on the The Daily Show to promote The Switch, where the conversation invariably drifted to that one awkward date they had in the mid-nineties. Jon explains (in weird, cloying detail) how young and cute Aniston was back then, how he had to ask her out on a date. To recap: they went to an Italian restaurant in downtown Manhattan, she brought all of her friends, he was sad, Aniston quips her friends were more important than mid-nineties Jon Stewart, they plug the movie. Oh, and Jon clearly still has a crush on her, which she coyly deflects for six minutes.

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Via HuffPo