Jon & Jen? It Might've Been

Aniston and Stewart had something similar to a date in the 90s

By Greg Wilson
|  Friday, Aug 20, 2010  |  Updated 11:16 AM CDT
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Jon Stewart thought he had it made when he scored a date with Jennifer Aniston, but when the actress showed up with a bunch of pals, it was clear she just wanted to be, well, friends.

Aniston stopped by Stewart's "The Daily Show" Thursday night, and the pair revealed the date, which came during the first season of "Friends," and before either had become A-List superstars. Stewart didn't even think Aniston would remember having dinner at an unarmed Italian restaurant on Manhattan's 10th Street, but she did.

"Of course I remember that," she said.

"It was lovely," Stewart recalled. "Here's what was nice about it that I remember, and tell me if you remember. You brought so many of your friends. And I remember thinking, 'She's so excited to be on a date with me, she wants me to get to know her posse.' "

"That's really sad," Aniston replied.

"In fact, I remember you just inviting random people from the restaurant to come sit between us," Stewart said.

It would only have been a year or two later that Stewart, 47, met his future wife, Tracey McShane, on a blind date. He famously proposed to her in 2000 through a personalized crossword puzzle and the pair now has two children.

Aniston got married at the same time to Brad Pitt, but they divorced in 2005.

The Daily Show With Jon Stewart Mon - Thurs 11p / 10c
Jennifer Aniston
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Selected Reading: The Daily Show, IMDB

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