Ouch! Pre-Fame Jennifer Aniston Put Jon Stewart in the Friend Zone

Longtime pals and coulda-been couple reminisce about their ill-fated '90s date

By Gina Serpe Aug 20, 2010 3:10 PMTags

Just think: if all had gone according to plan—well, according to Jon Stewart's plan—back in the 1990s, he could have been one-half of a superstar couple called Jonnifer. Or Stewiston.

On second thought, it's probably best that Jennifer Aniston just wasn't that into him. Even better is how she let him know it.

On what has to be he last leg of her publicity blitz for The Switch, Jennifer stopped by The Daily Show last night, where conversation with her longtime pal quickly turned to what could have been.

"You and I…you're not gonna remember this," Stewart began. "I asked you out. We went out to an Italian restaurant. And it was lovely."

Lovely, but not exactly intimate. If three's a crowd, their dinner date was a full-on swarm.

"Here's what was nice about it that I remember: you brought so many of your friends," he said. "And I remember thinking, well she's so excited about being on a date with me she wants me to get to know her posse."

Aniston, unsurprisingly, seems to remember the circumstances slightly differently, but with no less a subtle brush off for the funnyman. Ah, well. Can't win 'em all.

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